One Terrifying Lesson in Sales

Halloween was just upon us. Costumes, candy, screaming children, and spooky stories. And if you’re lucky, a glass of wine to soothe the nerves after a long evening of trick-or-treating. You might ask yourself, “How does this relate to sales?”

And you’d be right. It’s not easy.

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But let me try: there’s nothing more scary in sales than getting blindsided by reality.

Think back to a deal you thought was a layup.The prospect sounds excited during the Zoom demo. Their high energy is palpable. You can feel them leaning in. They seem eager to learn more. They ask you a bunch of buying questions. Pricing is even brought up. You allow yourself to think, “Wow, this is headed in the right direction. I can feel them pulling at me.” You can smell the sweet aroma of the commission check headed your way. As they run to their next call, they implore you to follow-up via email to schedule the onboarding session.

As a dutiful salesperson, you comply within fifteen minutes of hanging up. Superhuman indicates they’ve opened your email the next day. But no response. Five days go by. You reach out once again, trying to provide incremental value.

Dead silence.

You’ve gone from salivating at the celebratory steak dinner you’d enjoy to the crushing shame of missed expectations.

So what caused you to go from thinking you had a deal done, to their pulling a Casper on you?

In most cases: faulty tracking of the prospect.

Tracking the prospect is one the hardest things to do in sales. You’re supposed to take the current temperature of the deal all the while juggling the pitch, leading the sales interaction, driving to a close, and a number of other things.

“Is the prospect ready to buy?”

“Am I selling beyond the close?”

“Have I given them an opportunity to surface any objections?”

“Do they trust me enough to buy?”

Those are just some questions rattling in your head as you’re interacting with your prospect. You’re like an NFL quarterback; sensory inputs are coming at you from all angles. And you have to remain calm, self-aware, and execute methodically, despite the chaos around you and inside your noggin.

Fast forward a few months. You and I happen to work together, as you’re having issues closing the opportunities in your pipeline. As we start our engagement, you pull out a recording of this demo, and we launch into game film review. As we peer into recorded footage together, we observe a few things. At the tail end of the call, the prospect rushes as he leaves, and his energy actually feels a bit unsettled and almost dismissive. We notice something else: the prospect’s initial excitement about your product cools off after you introduce pricing. What we had originally thought of as a very positive call now seems difficult to negotiate.

Regrettably, we weren’t able to catch it live, as we were bumping up against our allotted thirty minutes for the call. Poor time management caught up to us. As we rushed to wrap up, we were in the midst of the action, and couldn’t fully perceive what was happening in front of us. Our inability to accurately track our prospect ends up killing our deal. Had we been more turned in, we would have spotted these issues and either addressed them head on during the demo, or scheduled more time to tackle them.

Tracking the prospect is a little bit like a Chef tasting a dish in the mayhem of a busy restaurant kitchen. You’re orchestrating the graceful chaos of making delicious food for a savvy urban clientele, and you need to keep your eye on the ball. The dish needs to be exquisite right as it hits the plate. This means you need to be fully present to taste the dish at all of its stages. If anything feels off, you need to adjust and right the ship. A pinch more salt. Too al dente. More sauteing needed.

If you’re not able to taste the dish accurately, you can’t be expected to make the right adjustments and deliver the succulent entrée to Table 6. Your gustatory discernment needs to be on point all evening long. Same goes with sales. If you don’t see your prospect’s intent and mindset accurately, you won’t be able to deal with their reality as it is. And without inhabiting their world, you’re likely to lose the deal. The Chef’s equivalent of putting together an unsavory pièce de resistance.

But if you’re on the money with your awareness of your prospect, you spot the gaps that need to be filled to bring the deal home. Sometimes, all that’s needed is a little Cayenne pepper to deliver the flawless dish. It’s on you to figure what’s missing or needed in your sales interaction, and then provide it. If you do, you’ll land a lot of deals that previously had you befuddled. Quite possibly, the difference between having a crappy quarter and seeing your name at the top of the leaderboard.

Startup Myth: “Our product sells itself.” 1 Myth, 1 Home Run & 1 Lesson – 2nd Installment

Myth: Our product will sell itself if we demo it well.

Founders and startup operators often say to me, “Our close rate isn’t as high as we’d like. Our demos appear to be going well, but a lot of our prospects don’t convert after that.” Post-demo drop-off is a widespread problem. If it’s happening to you, take a deep breath.

The phenomenon is befuddling. You clearly heard excitement from your prospect on your last Zoom. “This could be a great thing for us!”, they’d said. You could taste the sweetness of a landed deal. The contract went out for signature. But when it came time to sign on the dotted line, all you got was silence. The most frustrating part? Having zero visibility into what happened. You’re oblivious to the inner workings on the other side of the table. And you’re stuck on the fact you had an enthusiastic prospect that suddenly went dark on you. 

Here’s what usually happens when you go from excited prospect on a demo to him ghosting you. More often than not, you dropped on their “to do” list. When you’ve got a prospect on the phone or Zoom, they’re your captive audience. Because they explicitly agreed to the demo, there’s strong built-in intent and interest. They are primed and hungry to find out about your product and how it might make their problems disappear. When they get off the Zoom with you, they might actually be convinced that you have something they absolutely need. 

But then, life happens. Their dog gets indigestion and needs immediate attention. They’re in the midst of an all-hands on deck product launch that could change their company’s fortunes, and are expected to help out with QA for the next forty eight hours. Their kids arrive from school elated about a new take home project. What was once a Top 3 item on their to do’s slides down that list. And quickly. Buying a software product starts to feel like a distant priority behind the other tasks piling up at home and at the office.

The lesson here is this: 

It’s not enough to just sell your product or service. 

You need to earn your prospect’s time and attention through the sales process. 

That means that you should be constantly selling the next step. 

When I coach my clients on this, I suggest they ask themselves, “What will the prospect get from attending the next call? What will they get from reviewing the contract? What value will they get from sitting through your demo? What can you promise they’ll get by going through an onboarding call with you?”

If you’re able to answer these questions with real benefits — not to you — but to your prospect, then you’ve got something. It becomes about unveiling that value to them in an enticing way. 

Here’s how we sold our onboarding call when I ran sales at Whitetruffle. At the end of our introductory call, I’d say, “In our upcoming account optimization (fancy way of saying “onboarding”) call, we’ll make sure that you’re properly set-up on the platform so you can make the most of your 14-day trial with us. We’ll not only take you through all of the bells and whistles available to you in the product, but we’ll also put together your first few job reqs in such a way that you get the most qualified candidate matches on a daily basis. Lastly, we’ll give you tips on how to put together your company profile, so that you’re putting your best foot forward in attracting candidates.” Now, how does that sound, if you’re a prospect? Sounds like you’ll get a lot from the onboarding call, right? The tangible value of attending the call is crystal clear.

My first sales guy at Whitetruffle initially got a lot of no shows for this onboarding call. Once we brushed up his delivery of this end of intro call transition and made sure he was selling the account optimization properly, people started showing up to these calls in higher numbers. Those led to a ton more free trial conversions and more paid customers.

Home run: Epsilon3 founders went from thinking they had product market fit issues to 50X’ing their ARR in 12 weeks. That included closing the biggest deal in company history with a space company we’ve all heard of. 

I can still remember it. Our engagement was just a few weeks old. Epsilon3’s founders — Laura and Max — were downtrodden. They were doubting their product. Would the market accept it? They had been selling it for several months but hadn’t gained much traction. They told me, “Maybe we should build something else. Maybe this is a sign that the market wants something different.” The thought of scrapping their entire product had crossed their mind. I responded, “Guys, I think it’s a bit premature. I’d like us to have more market evidence before making such a sharp turn. What we have here could either be a product issue or a sales execution issue, or a combination of the two. I can help you remove the sales execution issue. And we can continue learning about the market’s reaction to the product. We owe ourselves that, before redirecting the ship in a brand new direction.” 

Deep down, Laura and Max agreed. After all, they had invested close to a year in product development. They needed to give their baby a fair shake in the market. 

I got to work on diagnosing the sales execution issues. A few things were broken. For one, free trials were extended indefinitely. They were rarely time boxed. And a lot of our free trial users weren’t converting to paid customers. We were hoping that folks would like the product enough during a loosey goosey trial period to then decide to pay us. We also had no way to figure out what constituted success in our trials/pilots. It was impossible to paint a picture as to what our trial users might expect during this phase. We desperately needed a way to control the sale.

Laura and Max pulled up their sleeves and implemented a ton in very short order. We installed a 14-day credit card activated free trial. We combined it with an onboarding call, which was a forcing function for our customers to enter in their credit card info. We instituted a sturdy qualification process, which ensured we wouldn’t demo to folks that didn’t match our ICP. We also worked to find out about the buyer journey in great detail early in the process. This enabled us to get in front of the decision makers quickly and therefore shorten our sales cycle. We got better at selling next steps, and booking the next call/meeting on the call we’re currently on. In conjunction with that, we stopped relying on email follow ups to book upcoming calls. Lastly, we figured out what success looked like during our trial and started setting those expectations for our trial customers. 

Laura and Max’s efforts paid off quickly. We 4X’d MRR in the first month of working together and we’re on pace to do even better in subsequent months. A sweet culmination came with the closing of a game-changing six figure deal with a space company we all know. When working on the opportunity, I told Laura and Max that if they got it across the line, I’d travel down to LA to take them out to a celebratory dinner. At the time of this writing, I’m packing my bags for a trip to Tinsel Town. 

Lesson: The more I am attached to the outcome, the less effective I can be as a coach. 

I have a confession to make. 

I get emotionally invested in my clients’ success. (And this isn’t some form of humble brag, I promise).

Too much so, at times. It can eat away at me when we’re not moving as fast as we could. Or when I feel like my message isn’t landing the way it should. Or that I haven’t done a good enough job communicating a lesson that I learned the hard way. When I brought this issue up to my own coach — the fact that I was really struggling with the powerlessness of my coaching role — he put forth the advice above. I thought it so good, I even took it into therapy. 

Everything starts with acceptance. If I can’t accept that my client is stuck, I won’t be able to help them shine the right light on their blockage, and consequently have it melt away. The more a client feels my need for their success or a certain outcome, the more they will resist any change I’m trying to impart. Trying to impart change, in the first place, isn’t the right method. Change must come from within. I can only help my clients look at an issue that might be causing them to get in their own way. I can suggest a way for change. Or a different way to look at things. The client — who is the player out on the field — must actually perform the change. There’s a ceiling to what I can do. I can offer the advice, the insight, the lesson, or even a path to change. But I can’t act on it. I have to be okay with my powerlessness at the end of the day. 

If I become too attached to the outcome, I’ll force things. I won’t be able to meet my clients where they are, and help them where they might be stuck. I’ll most likely end up pushing them too hard, and they’ll resist even more. David Hawkins talks about this in his book “Letting Go”. Human beings resist change if they feel they’re being pushed into it. As my therapist has told me on several occasions, you must “join the resistance”. It is important to shine the light of awareness as to why someone might be resisting. Only then can someone make a true change about how they act. Understanding and seeing the blockage is the catalyst to change. Seeing the contours and shape of the resistance will in most cases dissolve it. But the person doing the self-examination must actually want to be different. 

Once you understand that, you can see that wanting success for your client is about you. Not the client. If helping your client is about meeting them where they are and not pushing them towards change, then being attached to an outcome is not only counterproductive. It’s also putting yourself ahead of the client’s progress and needs. In order to best serve my clients, I need to put their needs to be supported over my need to be a “successful” coach. In essence, I need to get over myself in order to be at my most helpful to others.

1 Myth, 1 Home Run & 1 Lesson

Myth: When writing outbound copy, being formal or professional is helpful.

We’ve all seen them: stiff emails dressed up with ‘formal’ or ‘professional’ words. We reach for the Delete button before we’ve finished reading the entire subject line. 

Here are some examples:

“Introducing [BrandName]”

“[BrandName] will solve [YourProblem]”

“[BrandName] is part of Gartner’s Magic Quadrant”

There’s two reasons these emails don’t work: they feel like sales pitches, and they look like every other sales email clogging up your inbox.

Professionalism is important in business, but ironically the best, most successful sales emails are personal and informal. They’re crafted to feel catchy and elicit your curiosity. 

Here are example subject lines:

“how are you solving [YourProblem], [FirstName]”

“you alive, [FirstName]?”

“feeling like Tom Cruise yet, [FirstName]?”

These spell out your first name, which naturally captures your attention (and is more than can be said for 90% of cold emails).

The same rules apply for the email body. Write as if you’re dashing off a note to a close friend. Let your personality out. Include humor. Don’t hesitate to write sentences all in lowercase. This is an opportunity for you to loosen up that necktie and put on your loafers. 

Here’s one I wrote wearing my weekend shoes:

Hey [FirstName] — how’s normal life Post-COVID? For me…it’s been exhausting interacting with friends more…I’m sure that’ll pass soon. I used to think I was an extrovert haha…

Speaking of exhaustion…how’s your accounting team performing? This time of year work is a little hectic and productivity is under a microscope. People like you keep telling us they’re not getting enough from their existing headcount. 

We’ve built software that organizes your accountants’ work and allows them to be a lot more efficient…36% on average. Disney, Coca-Cola, and BCG are among the teams that already use us. 

How about a quick call early next week to see if there’s a fit? All it’d take is 10-15mins. How does Tuesday afternoon look to you…?

Let me know…would love to connect!

Take care,


Now…how did that feel? Quite a bit more personal right? It could even pass for an email that’s not automated. And yet that’s the key to success in automation. You want to industrialize your process, all while your touch points feel personalized. Be as colloquial and as casual as possible.

At the end of the day, prospects want to buy from a human being, not a faceless corporation. To see your reply rate increase, write like you would to a friend, and let your humanity shine through.

Home run: Last year, while many companies were spinning their wheels figuring out how to survive, my client 3x’ed their MRR in 12 weeks.

A trends startup approached me late Q1 last year with a major problem. They were getting a ton of inbound interest — including from household names — but very little was converting to actual sales. The founder pair had garnered a ton of attention through PR, content and thought leadership, but next to nothing was hitting their bottom line. Recognizable brands said they wanted their product, but traction was minimal. The few deals they were able to land were far too small. The founding team wondered if they were ever going to hit product market fit, as they had been floundering on the sales front for over a year. Their runway was limited. So, they needed to get to ramen profitability before time ran out. One co-founder told me, “We need to make more money…for the survival of the company.” To make matters thornier, the pandemic slammed into us as we started our engagement. Would our customers suffer from budgetary contractions? Would fear play a role in their buying process?

As I stared into their sales funnel, I spotted major leaks. Folks were initially interested in the platform but weren’t jumping on a call with us. They came to the site and signed up for access to the platform, but somehow didn’t want to talk to us. We had little shot at making the sale as things stood. Once prospects did join us on the initial call, most of them didn’t stay in our sales funnel. Free trials were not converting to paying customers. We needed to patch things up. And quickly. 

What could we use as a lure for that first call? I wanted something that would compel them to attend. Without much delay, we came up with a consultation session. That first call was not only an introduction to the platform, but also a consultation where the salesperson delivered trends and insights. The prospect left that first meeting not only intrigued but wowed by the understandings they had gotten. They could walk into their next team meeting and flex their newfound industry knowledge, “Did you know that we’re seeing increased demand in [product category]? A 37% increase in North America over the next 2 months, as a matter of fact.”

Before ending our first sales meeting, we promised them even more on our next call: we’d help them answer some of their company’s major strategic questions. This second call was about unveiling the platform tailored to their needs. It was also about us getting them started on their credit card activated free trial. And setting them up for success for that initial stretch and beyond. 

Once changes were in place, our two punctures were plugged and our sales process started humming. All of a sudden, our steady flow of inbound leads now turning into greenbacks, and we were off to the races. 

The biggest lesson here is this: we transformed the customer experience. Offering demos to folks that had been curious about our data product wasn’t enough to get leads to convert. No prospect wants to sit through yet another product demo. Delivering personalized, actionable insights on a silver platter was the key to having them make their way down our sales funnel. And ultimately to a closed deal.

Lesson: The selling part is easy. It’s the “not selling” part that’s hard.

This gem was uttered by my coach several months back, in the context of selling my sales coaching services. It stuck with me ever since. Here’s what he meant. We all know the major selling points of our product or service. At a basic level, we know how to articulate those value props, and even handle major objections. And once we have some sort of sales process in place, we know how to lead the prospect through it, and get the deal across the goal line.

What’s much harder is to recognize what’s happening in our prospect and pull back at the appropriate times. Sales is about recognizing when to pour it on, when to sprinkle in a pinch of selling and when to not sell at all. Just like a good sauce, it must taste just right. A top-level Chef will intuitively know when to make the necessary adjustments to her dish. She’ll keep tasting things, tunes into her senses, and steps in with a pinch of salt at exactly the right time amidst the madness of her kitchen. Sales works the same way. Despite the many things going on around you, the feelings you’re managing on both ends, you need to be acutely tuned into your prospect. You might ask yourself the following questions, “Are they already sold?” “Are they ready to move on to the next step?” If you’re getting resounding “Yes’s”, then it’s time to move things along.

The last thing you want to do is keep selling when the prospect is either already sold, or is selling themselves. If the deal is already closed, you want to discuss next steps; which typically include things like payment, contract, and onboarding. If the prospect is selling themselves, you want to get out of the way. Few forces are as strong in sales (or otherwise) as someone convincing themselves of something. In those cases, you want to let them do the work for you. Adding in anything at that stage is only intruding on their cognitive journey. You risk derailing them. That’s when you want to let them talk and work their way through to a closed deal.

That doesn’t mean prospects won’t get to a point where they need a little nudge from you. They might even run into Everest-sized objections that you’ll get them over. But, the key here is to recognize when you need to intervene and when you can let the prospect close themselves. The ability to recognize when not to sell and actually shut up is an advanced form of sales.

Which leads us to the counterexample: a terrible sales experience. Most of us have felt the pain of a salesperson not being in-tune with their environment. They fail to understand what’s happening in front of them. They keep pushing something that doesn’t need to be pushed. You might already be convinced that you need their product, but they haven’t switched off their sales pitch. They lean in and insist, “You should really consider our solution for the issues you’re facing.” And you think to yourself, “I’ve been giving you buying signals that I want this thing for the past thirty minutes. Let’s move on already!” Depending on the prospect’s patience, the salesman’s tone deafness could end up costing him the sale. Had he known that his sales sauce tasted delicious, he might have left the dish alone, and been on the way to closing a deal.

So next time you’re selling, keep your antenna up. Track your prospect. Taste the sauce. What are they telling you? Are they sold already? Can you move on? If so, it’s time to use restraint. Adding in more selling would only ruin the dish. And the deal.  

Selling Through Crisis

It’s been a series of tidal waves. First came the news of a virus coming out of Asia’s wet markets. Then came the cruise ships that were floating petri dishes. Then the growing number of cases in countries like Italy and China. Then our sheltering in place orders across most US cities. And now the growing number of domestic and global cases.

There’s no question it’s a terrifying time for all of us. A natural instinct may be to crawl up in a big ball and hibernate. Or even worse: panic. When this quarantine first hit us, my therapist told me, “The Chinese character for crisis is composed of danger plus opportunity.” We are undoubtedly faced with a dangerous situation. But our only choice lies in how we respond. Despite the chaos around us, we always have the option to pull ourselves up by the bootstraps and establish a plan of action. We need to make the conscious choice of seeing opportunities where they lie, and pursuing them relentlessly. Here’s how I would think about sales in this Coronavirus reality.

It’s Prime Time for Building Pipeline

TV executives have known the concept of captive audience for the longest time. They have programmed their best bits for the boob tube on nights where folks are at home. Just look at television schedules today. The most successful shows are more than likely on nights where folks are at home: Monday, Thursday, and Sunday nights, for example. It’s no secret the NFL — who routinely has the majority of the top television shows by ratings any given year — has ended up on those nights. Radio executives have lived by this as well, putting their best programming during “drive time”, when folks commute to and from work in their cars. Commuters are captive in their cars, and in desperate need for entertainment. Radio is their best and perhaps only option. 

More than any other time in recent history, you have a captive audience of folks confined at home, with unprecedented access to technology platforms we can broadcast to. Our shelter in place orders have forced us in quarantines and have severely limited our in-person social interactions, so we’re seeking connection online. As social animals, we are confined in tight spaces and are craving social interaction and mental stimuli more than ever. And it’s happening all over the world. That’s a clear and gigantic opportunity for you to come in and create conversations.

Barring having small children that need constant attention, most adults will want to chat and will be open to doing so. Their distractions and outside activities have been dwindled to next to nothing. If you nail tone in your outreach (more on that later), you’ll be able to build up a glut of pipeline in Q2, which you’ll be harvesting in Q3 and Q4. 

Now, going through procurement or even closing complex sales is going to be tougher as folks are more disconnected than ever. Yes, we’re getting better at working remotely, but most organizations haven’t worked out the wrinkles of that yet. It’s also tougher right now to create urgency down your sales funnel and drive deals to a close. If I was a founder or a head of sales, I would put a lot of my energy into starting a lot of conversations and building pipeline. I would actually double down on it. I might even move some of my AEs to prospecting. This abundance of opportunities is something you’ll collect on in the latter portion of the year when things start getting back to normal. Companies that adopt this strategy will end up saving their year. 

If you thought this was only theoretical, I’ll submit that we’re seeing early signs that top of the funnel activities are generating more results right now. Within my consultancy, we have seen a decrease in Cost-per-Lead on Facebook, and also an increase in open and reply rates on outbound email in the past few weeks. 

Communication: Nail Your Tone

If you’re going to focus your efforts on generating opportunities, your only risk is not nailing tone in your communications. People are especially touchy these days, and reaching out with messaging that could be considered insensitive can turn people off very quickly. So you’re going to want to be extra careful. Lead with empathy. 

Your stance is going to be that of a waiter at a restaurant with a general message of “How can I help?” rather than “This is why you should use our product!” You’ll score points being extra friendly and informal during this time. Remember, people are most likely starving for human communication and intellectual stimulation. Think hard about that as you’re putting together your messaging. Salesy emails are not likely to land well during this time. Don’t push the sale, but tell prospects it might be worth having a quick conversation to see if there’s a fit. Think about including a personalized video message to your prospects. Seeing other human faces matters to all of us; particularly right now. Think about honoring each person’s humanity. Build relationships. In our startup community, founders are well known for asking each other out to coffee to share best practices and exchange feedback on their respective products. That’s the type of feel your messaging must have. If you go about formulating your outbound emails this way, you are going to start booking a lot of introductory calls for yourself, during this time of crisis. 

And remember, when you do chat with folks, make it about them, and their pain points. Nobody wants to have a product shoved down their throats. Nobody wants you to tell them about your product’s benefits, unless it applies to them. Especially now. You’re going to want to lead with pain points more than ever. As a close friend of mine told me a few nights ago over FaceTime, “This is a good time to get back to fundamentals.” This climate will be less forgiving to faux pas’, or clumsy communication. If you’re buttoned up, you’ll do just fine. 

Closing Deals: Focus on ROI

Now what if you did want to close deals during this time? What things do you need to consider to actually get deals moving down the funnel, and across the goal line? 

Three letters: R-O-I. 

With the contraction happening in the economy, your prospects are getting very cost-conscious. There’s no room for fluff. Selling with charisma or personality will not suffice. The rubber has met the road. And we need to make sure that products generate a positive ROI. And it’s important to articulate that in very simple, digestible terms. 

Let’s take a quick detour to illustrate my point….Hiring freezes and layoffs have already commenced. And more are coming. If you sell a tool that is supposed to enhance or empower a group of people within a business, this is your time to act. Folks will be looking to increase the productivity of their existing teams, without the need to add headcount. If you can prove to them that you can add a team member’s productivity, then you need to make that case right away. That will ensure that you close deals, even in this climate. Several years ago at Whitetruffle, where I ran sales, we used to sell an Agent package, which leveraged our talent sourcing platform and layered on a human component. We would have a person internally that would have a quick conversation with sourced candidates, in order to prequalify them, before we sent them to our employer clients. Our pitch to employers was that we could delay their hiring of a sourcer. Instead of paying a $80K – $90K salary per year in a city like San Francisco, or New York, you could hire us on a month-to-month basis for $3K/month. The ROI case was easy to make: it was $36K on demand versus $80K for a full-time hire, not counting benefits. And you could delay any real hiring. If you can make a similar case in this climate, you will have a good chance of closing.

If you’re formulating your sales strategy (like a few of my clients are currently doing), it’s time to think hard about the newer constraints that have been thrown into the mix. Folks are going to be more skittish about spending a large amount of cash in the immediate future, unless you are able to convince them there is positive ROI. You might have to extend trials or offer flexible payment terms to prove even more value upfront. If you can find a way to land and expand right now, I’d highly recommend it. The idea is this: if you can get people on the sauce at a lower price tag — without going through procurement — you’ve got a shot to land and expand later on. Think about pricing per seat and allowing people to pay for your product with their own credit card, before recruiting more members to join once you have delivered a ton of value. Lower the bar for entry, and let your product do the selling. That type of strategy is more than likely going to succeed in these difficult times. 

Spring Cleaning: What can we do better? 

You hear of people doing “spring cleaning” activities during this hiatus. It’s your chance to do the same thing within your sales organization. Look at your tool stack. Do you really need that Nth tool? Is it delivering value? Is there a different tool you’ve been meaning to try, that could provide a productivity boost or eliminate operational inefficiencies? Now might be the time to get on a demo with the vendor and/or sign up for a trial. 

Examine your sales funnel. What conversion rate can you take a stab at improving? What things can you install to make it better? Review your staff. Who needs extra training right now? Who can I help level up? What can I do to make them better salespeople? These are questions you should be asking yourself at this time. 

We’re usually so busy running around and chasing deals, that we don’t take enough time to take stock and regroup. This is just the time to engage in that type of thinking and strategizing. Tidy things up within sales. This little bit of slow down allows you to take stock in your sales model and work out some of the wrinkles you might have been ignoring for quite a while. Take the space to see what’s working and what’s not, and start putting in place initiatives that can fix your issues. 

Overall, it’s most important to be flexible with your approach. Many rules have been thrown out the window in a matter of weeks, and adaptability will be a major factor for companies that emerge from this period. Resistance to change, or clinging to old strategies will be an impediment to survival.

If you need help during this trying time, email us for a free consultation about how to set your startup up for a successful 2020. Feel free to drop me a line at to schedule a time. Be well and stay safe!

Email is an ad unit (and other advanced tips for outbound)

Several months back, I wrote about learnings I had garnered while building out outbound for Whitetruffle a few years ago, and with several of my consulting clients more recently. That first installment was meant for you to go beyond outbound best practices you probably read about online. The following is meant as a second chapter, weaving in even more advanced insights that weren’t included in the original.

Email is an ad unit.

Email is an ad unit, but it can take a moment to see why. Email feels invasive and superfluous. It infiltrates your inbox in overwhelming volumes. Some office workers view it as a to-do list that’s been forced upon them; touting their all-too-few “inbox zero” moments, which have become synonymous with peace of mind.

But thinking about it in such a way misses an opportunity to see email as a significant channel in your go-to-market arsenal.

How is email an ad unit, and a sophisticated one at that?

Email is a direct channel to a prospect transmitting a message that — if well-crafted — compels them to act. In most cases, this action is to (we’ll look at in the B2B sales realm, here) respond to the email and agree to an introductory call. When seen that way, email is a type of ad, that inspires its audience — the individual prospect — to act.

“What makes it a sophisticated ad unit?”, you might ask.

Well, email is incredibly personal. It is one-on-one communication that lands in an inbox that belongs to you and you alone. You get the sense that the author is writing to you solely, and to no one else. This creates a sense of intimacy that a billboard in Times Square, or a radio spot on national airwaves will never possess. Even when you’re broadcasting email to your targets in massive email campaigns — if done right — it feels like narrowcasting to each individual prospect. Or at least, it’s supposed to feel that way. More on that later.

Second, email is targeted to the utmost. You chose your targets in your lead generation process. You defined your Ideal Customer Profile based on who you believe is your ideal buyer, before even sourcing your leads. You know exactly who will see your messaging down to the company, job title, first, and last name. With other forms of advertising, you’re not quite sure who gets to see your ad. If you’ve bought space on a billboard along the 405 in Los Angeles, you can only hope your message hits folks that are likely to buy. But, you have no assurances. Same goes with radio advertising. Or TV ads. This leads marketers to utter John Wanamaker’s old truism, “Half the money I spend on advertising is wasted; the trouble is I don’t know which half.” Email is just the opposite. You know exactly who the recipients will be, and provided your customer profile is dialed in, there’s little wasted money or impressions.

Third, you have the benefit of knowing you can have several, more in-depth interactions with your prospect with email. With a good chunk ad units, you’re lucky to get one interaction: an impression, and if you’re lucky perhaps a click. Even when retargeting digital ads, you might get a few more clicks on the ad over the lifespan of the cookied user. But you won’t get the breadth and detail of feedback you might get through email. For broadcast media, like radio ads, it’s very hard to even track the effectiveness of your ad units. You buy ad units on a broadcast outlet, your ad is read on the air, but you rarely get feedback on your messaging from the prospect. More often than not, it’s very difficult to even track the impact of those types of ads. With emails, not only can you track the effectiveness of your messaging, but you can have several exchanges with the prospect. You are getting more feedback on your messaging per impression, than virtually any ad unit. Did you happen to leave your prospect confused with the value propositions you put forth? Were you able to clearly and concisely express how your service differentiated itself from competitors in the market? Were the value propositions you led with in your messaging the same ones that led your prospects to buy? What short message will likely grab the prospect’s attention? Responses from prospects to your emails act as direct feedback to your messaging. They let you know if they are confused at how you describe the main value proposition, or how you differentiate from the competition. You’ll be able to take those responses and iterate on your messaging. When your email messaging becomes crisp, you will know it. And you’ll be able to use the messaging company-wide. It’s wording you’ll work into ads, marketing communications, press releases, investor pitches, etc.

Fourth, email has several different components you can optimize for best results.

The first component is the subject line. That’s your business opener. Your pickup line. If you’re unable to get people to open your email, it doesn’t matter what you have in the email body. The email could very well be blank, if no one opens it. When I run campaigns, I try to hit an open rate of at least 40% (for the entire campaign) before focusing on the email body. You have very few characters to work with, so it’s important to be compel your prospect to click on the email. I’d encourage anyone to play with many different variations early on in your outbound buildout. When the data comes back, pick out the best performing subject lines and build around those.

Once we’ve hit that 40% open rate marker, we can focus on the second component of our ad unit: the email body. The copy contained within the body of the email is supposed to pique the prospect’s interest and get them to book an introductory call with the sales rep. You can be lengthy here, but it’s actually recommended to keep things short, sweet, and — believe it or not — informal. Getting a call scheduled for a rep or a founder contains two main conversion points. One is an actual response — an event we try to get at least 6% of the time, for the entire campaign. The other conversion point is an interested response — one that is captured by the Interested Rate. We try to hit an Interested Rate of 2-3% overall. The Interested Rate the most single important metric in outbound, as it represents the number of interested responses you’re getting back from prospects. Although we aim for a 2-3% conversion rate for interested replies, anything over 1% is considered a successful campaign.

The complexity of email is the reason why I never start out sending out large campaigns when I do an outbound buildout. Cranking things up prematurely will only cause you to burn through a large amount of leads prematurely. Early campaigns should range from 50 to 150 emails. Never more. Once we reach 1% interested rates, then we’re ready to scale things up. Before then, it’s premature. Unless the company has short term revenue targets to hit. That’s the only exception we’ll make. We’ll sacrifice leads in order to hit those targets, if need be.

If you allow yourself to look at email as an ad unit, it will brighten your outlook on it and make you a better email marketer. Email has been under fire in recent years. Folks in Tech have been clamoring for a better alternative. Meanwhile, email seems to be doing perfectly fine, as a mode of communication. Viewing it as an ad unit will allow you to become sophisticated about its various components, and allow you to craft more personal, punchy messaging that will generate more interested responses, and consequently, more intro calls.

Now that we’ve got you engaged about the medium, let’s get into some practical tips about how to make your outbound more effective.


Leverage founder-to-founder (or CEO-to-CEO) empathy

A few months back, I was working with a client on their outbound buildout. We had been slaving away at it for a couple of months. But, we weren’t hitting our conversion metrics. More specifically, we were having a hard time getting prospects to respond favorably to our content. Our Interested rates and Response rates were far too low.

In an attempt to change our fortunes, we decided to think about the problem differently. Instead of targeting Product Managers with a sales rep, as we had up to this point, we thought to ourselves, “Why not try leveraging the inherent kinship that exists between fellow founders of startups?” My client — a start-up — had a founding CEO with a good reputation and friendly demeanor. When I first brought up the idea of using him as our outbound point of contact, he was not convinced. I had to cajole him a bit, into trying this new idea. I pushed forward, “Listen, why don’t you let me run this campaign? We’ll create a new email address for you, and I’ll manage your inbox. I just want to be able to use your persona and establish some kind of connection with these folks. It will be a welcome departure from what we’ve been doing. We all know PMs don’t want to talk to a rep.”

He finally relented. And our new campaign was off and running. Within a couple of weeks, we knew we were onto something. We were finally getting responses back. Folks were actually interested in booking introductory calls with us. We had gotten our foot in the door. A large victory, for this client.

Now, why did this work? Why would a founder respond favorably to another founder?

There’s an inherent closeness between founders, that’s been forged by common intense experience. Despite working for different companies, you’re in the same foxhole together fighting the good fight. It’s you versus the world. You’re the anti-establishment new kids trying to bring down the industry incumbents with your radical approach. Very few people can relate to the pressures you face on a daily basis. You have to answer to your customers, investors, and employees. You have managed to build a business out of thin air. This extreme life you’ve chosen it not one many can stomach. Those that do take the leap automatically recognize one another. The bond is unspoken and already exists. All you need to do is remind your fellow founder that you’re here, and in it with them.

This approach works with CEOs as well, by the way. There, the kinship has a similar flavor. Even if the CEO hasn’t founded the company, it’s a lonely role at the top of a company. CEOs tend to understand one another, and bond at a very basic level.

Here’s an example of founder-to-founder copy that has worked in the past for me:

Hi {{first_name}} – I’m reaching out as a fellow SaaS founder to chat about ways to make [short phrase about high level value props]. I’ve been aware of what you’re up to and I’m interested in helping.

I’ve founded two companies ([Company1}.com and recently [Company2].com) and bootstrapped them to scale (X+ employees currently) by helping out other SaaS companies [do what your company does].

If we’ve piqued your interest, our team would be happy to chat sometime and offer some informal feedback.

What do you think?

Ask for feedback as a call to action in your email.

As you may have noticed in the copy example above, I am not selling hard. It feels a lot more informal. More, “let’s have a cup of coffee” and less “let me give you a presentation on the stellar benefits of our solution”.

One of the ways you get into the good graces of people is by asking for feedback rather than offering it. It’s a great conversation starter. People love giving it out. You’re propping up your prospect as an expert in her field. And you’re putting yourself in a humble and vulnerable position.

Anyone with a good conscience will most likely be swayed into being a good samaritan and help you out. And with that; you’ve got a conversation with them. Because you’ve made the prospect comfortable and valued, there’s a great likelihood they’ll start opening up about their issues. And all of a sudden, you can start soft selling based on what the prospect is confiding in you. You’ve built a trusted relationship with someone that was initially a cold prospect. If you’re subtle about it, the actually selling become the easy part. It’s all downhill from here.

Here’s an example of email copy I have used to ask the prospect for feedback:

Hi {{first_name}} – I’m a fellow founder looking for a bit of feedback on my new product: a way to [Short pitch about what the company does]. It’s like [Example company everyone knows], but [A different market].

Do you have one ‘wish list’ of features you’d like to see for what we’re building?

For background, we’ve helped companies like [Example Customer A] and [Example Customer B] add more [High level value prop] in a few weeks.

I’m trying to build a list of the most requested ones – so any feedback would really help 🙂



So next time you’re having a hard time booking calls with your current email copy, throw in a feedback request, and see how that works for you. In the startup world — where folks are always curious about new products and new trends — there’s an even greater chance you’ll get a favorable response from a fellow alpha user. And starting from a place of feedback will allow you to sell more effectively. Next thing you know, they’ll not only open up about feedback on your product, but also on the needs they have as a company.


Do not try to sell your product or service in one email.

In sports, there is such a thing as “trying to do too much”. At times, in baseball, the correct percentage play is to bunt the runner over; not swing for the fences. At certain situations, in football, all you’re looking to do is to get that first down, move the chains and buy yourself a new set of downs. You’re not looking to score in one play when you’re backed up at your own 10-yard line.

In the very same way, in outbound email campaigns: don’t try to get the transaction with one cold email. That’s simply unrealistic. Even asking the prospect to sign up to a free trial is asking too much, in many cases. Your goal should be to generate an introductory call.

That’s it.

If you start thinking about selling your product outright, your copy will be too long. Your message will be diffuse. You’ll run the risk of losing your reader in long feature lists and other benefits. Your message will most likely come off as a hard sale. Instead of bunting the runner over, you’ll end up striking out because you wanted to hit the ball out of the yard when all you need to do is get a runner on base.

Here’s an example of email copy that tries to do too much right off the bat:


I am reaching out because we’ve developed innovative software that will alleviate your headaches as a CFO.

Our software enables large companies to reduce their accounting costs by 68% on average, by reducing the amount of manpower needed and by increasing efficiencies.

Companies like Apple, Google and Facebook all use us, and have all expanded their relationship with us over time.

We’d like to include you to our client list. Feel free to get started with a free trial here.

Let us know if you have any questions.



If I were to be approached by this type of email, I would be very much turned off by it. The sales rep has no intention of getting me on the phone, nor the willingness to answer any of my questions. Nevermind do a demo of the software. The email does a good job of establishing credibility and social proof, but it falls short in that it tries to convert me right away without offering to handhold me through the process. This is an example of an email that tries to get to the free trial too quickly. Even folks that don’t like to chat with sales reps will feel a little awkward by the above approach. You might get a few folks to convert to a free trial, but the vast majority of folks will not react well. They more than likely won’t click on the link, nor will they respond to your email.

With a few small changes, the email copy becomes more palatable to your prospect, and increases your chances of eventually closing them:


I am reaching out because we’ve developed innovative software that will alleviate your headaches as a CFO. And we thought this might be relevant for you at [Company].

Our software enables large companies to reduce their accounting costs by 68% on average, by reducing the amount of manpower needed and by increasing efficiencies.

Companies like Apple, Google and Facebook all use us, and have all expanded their relationship with us over time.

What’s a good time for a quick introductory call next week?

I’d love to learn more about your business and see if we might be able to help.




If you start thinking that way — getting that critical first down instead of throwing up the Hail Mary — your copy will reflect that. It will be short, crisp and to the point. And your prospect won’t feel like you’re moving too fast with them. The email’s sole purpose will be to pique your prospect’s interest enough to have them agree to a quick call.

Commodity products or services will (most likely) not get high response rates.

One of the keys to outbound emailing is that you grab your prospect’s attention. First, with your subject line — to generate an “Open” — and then with your email body — to generate an interested response.

Imagine trying to grab your prospect’s attention if you can’t differentiate. Without being able to stick your neck out and say, “this is why we’re different and better than the competition.” Without telling them first why you are worth paying attention to, and then why you are above the competition. Products or services that are commodities — undifferentiated, for the most part — are invariably going to struggle with outbound email.

As an example, if you’re a development shop, and you’re mulling over whether or not to do outbound, think again. Even if you’re faster at deploying features, or more rigorous about doing QA, there’s a good chance that’s not a strong enough differentiator to tout over email and generate interested responses. You might be much better off relationship selling with a charming salesperson that will make friends with your prospect and inspire them to sign by their very likability. The differentiator — in this case — will not reside in the service, but in the salesperson.

Do not use calendaring software to schedule the initial call.

It’s one thing to use a calendaring tool like Calendly with an inbound lead. You have strong intent from the lead. They are very interested in having a conversation with you, as they have taken the time to fill out a detailed online form. Although I don’t always recommend it even in this scenario, you might well get away with it for that reason.

When it pertains to outbound, sending someone a calendaring link asking them to do the scheduling with you themselves is never a good idea. And yet, people do it, these days. Let me remind you: as the sales rep, it is your job to chase after the prospect and earn their business. Sending a calendaring link puts the onus of scheduling your first real interaction on a prospect that has just been cold emailed. It’s just not a good look to ask them to do that. Bad form very early on. As they are mulling over whether or not to answer your cold email with some interest, you are then asking them to take on the extra work of looking through your calendar and booking a time.

Always do the work of scheduling the introductory call with the prospect. You’ll start the conversation on the right foot.

Make sure your first line or two of email body copy are attention-grabbing.

You might say, “Well, that’s not really insightful. Everyone knows you want to hook people early on in your copy.”

And you’d be right.

The insight comes here, however.

Imagine yourself in the following situation. You’re having a very busy Monday. Your boss is on you about a report you’re behind on. Around 12:30pm, in a small gap between calls, you decide to pop out of the office to pick up some takeout from the nearest food truck, a few blocks away. As you arrive, you wince at the line that has already gathered. You bite the bullet and opt to wait the 10 or so minutes it will take to finally order your food. In need of distraction, you naturally look down at your phone and check your email…

This is the typical scenario you need to think about when generating email copy. The subject line and email body copy must be so good that it would grab the caffeinated, overworked version of yourself during a quick lunch break and prompt you to respond with a time for an introductory call.

Layer on the fact that you’re working with limited real estate on mobile devices, and you’ve got to make sure your copy is attention-grabbing right out of the gate. Not in your fourth or fifth sentence. But more like in the first.

The message needs to be punchy early. And it needs to compel your prospect to keep reading and then respond in a favorable manner.

Here’s how this translates to your email copy writing. Reduce your pleasantries up top. Nobody feels like you truly care when “you’re hoping they are doing well”. Get to the point. And lead with your best value right away. Do away with product features or functionality. Folks don’t buy products because they have features. Lean towards being very direct, even if it initially feels uncomfortable at first. You want folks to be able to read your first couple of lines on their cell phones in-line at the grocery story and respond with times to connect by phone before they get to the cashier.

An example is useful here:


Is [Company] spending an inordinate amount of time identifying clusters within customer behavior?

Acme’s interest-driven analytics engine will take care of that for you.

For example, our customer [Example Customer A] found new user clusters in 10% of the time it would have previously. WIthout doing any of the manual work.

Could this tool be useful for [Company]?


When you next find yourself working on email copy, visualize yourself as that stressed office worker taking a fifteen-minute break to pick up lunch. Can your copy be good enough to capture that person’s interest as they wait in line, and have them respond with times for that first call?

Outbound is one of the most rewarding things you can do in sales and marketing. You go from having no conversation going on to knocking down a door, and getting yourself in front of the prospect. Before building out outbound, you had no way to pitch your product or service. With effective outbound, you get yourself a ton of at bats and a chance to materially affect revenue. With that in mind, make use of the above tactics and the ones you might come up with. Let us know how they work out for you.

How to take your outbound sales to the next level

You’ve just figured out an early path to revenue. A basic way to sell your product. It’s not a bulletproof process, but it has garnered you a few logos on your site, and a couple of testimonials from happy customers.

You’re thrilled that your new product is starting to get real traction. The gestation period — the twelve previous months of product iteration — are finally starting to pay off.

To get here, you’ve relied on introductions from friends, fellow founders, and your investors to get you in front of prospects. This is great; but you know it’s not scalable, and you’re getting the sense that your network will soon be tapped out.

How are you going to go from a handful of paying customers to your first 50 or 100?

I’ve found that an outbound strategy is one of the best ways to get you in the door with a large number of potential buyers.

I didn’t fully realize the power of massive outbound until I was at Whitetruffle and in charge of building out the top of our sales funnel. As Head of Sales, I had established a reliable sales process. We were closing business at a good clip, once we came into contact with prospects. What I was missing was a predictable way to get in front of a large number of potential customers. That’s when we started to take a serious look at outbound. 6 months later, our initiative hit its stride. Once it did, it was a veritable infantry. June 2015 saw us have our highest nominal growth month, and we crossed the $100K MRR plateau. 50% of our MRR growth in June was attributed to our outbound efforts.

At that point, I was sold.

And the beautiful thing about outbound is that when it’s humming, it’s entirely predictable, as Aaron Ross covers in his book. You know that adding X leads at the very top of the sales funnel will garner you Y in incremental MRR at the very bottom.

That kind of reliability is exactly what you want as a sales leader or CEO. Board meetings get a lot less painful when the forecast you’ve given your investors actually hits.

Having now built out outbound for Whitetruffle and for several consulting clients, I’ve gathered a few insights along the way. I’ve tried to stay away from the basic best practices covered in depth elsewhere, and focus on what I’ve been able to learn that wasn’t initially obvious. Here are some learnings to consider.

Be patient, but resilient. Outbound can take a long time to get right.

At Whitetruffle, it took us about 6 months for our massive outbound initiative to really starting firing on all cylinders. I usually tell folks I work with now to plan on at least 3 to 6 months before massive outbound clicks in.

There are plenty of variables to test in outbound:

  • Subject Line
  • Email Body Copy
  • Calls-to-action
  • Targeted Decision-makers
  • Email Campaign Length
  • Geographical Regions

Iterating on these can take quite some time. Particularly when you factor in that the first few weeks are usually dedicated to subject lines. And that most campaigns take a minimum of two weeks to finish.

Iterating on your targeting is key.

At Whitetruffle, it took us several months to really nail our outbound initiative. In June of 2015, after 6 months our outbound initiative finally ended up contributing to half of our new business and our highest MRR nominal growth month in the company’s history.

What happened for us to get there?

We had to iterate on market location and decision maker. We also had to find the right type of customer: folks that could buy and stay with us for a while. Factors like company size, churn, targeted decision maker are all things to think about and iterate on as you move forward with your outbound campaign.

If you’re selling a software solution to CIOs of tech companies, you probably will want to target tech hubs in the United States and across the globe. Think San Francisco, New York, Austin, London, Berlin. If you’re selling fishing equipment to fishermen, you probably want to stay away from the state of Iowa or Belgium (all land-locked regions).

When thinking about who to target within an organization, asking yourself this, “Is responding to email part of their job?”

The other day, I was talking email marketing strategy with my friend Conor Lee, CEO of HipLead. We were discussing how best to think about targeting decision makers within an organization. In our conversation, we were enumerating the pros and cons of reaching out to certain types of decision makers. In his inimitable way, he immediately distilled how one should go about thinking about targets: “If their job is to respond to email, you’re going to get higher response rate.”

Software engineers are known for not liking email, for example. They tend to be in a lean back posture and can take up for several days to respond, if they even do so. That’s because they rightfully make their living in their code, actually making product (plenty has been written about the Maker’s Schedule). That’s where their bread is buttered, every single day. Salespeople, on the other hand, earn their paychecks (and commissions) by being very responsive to incoming emails. Over the years, it has been drilled into them to respond as promptly as possible. Closing the next deal may well depend on it.

All things being equal, you’re going to want to go through a salesperson versus an engineer. The salesperson is much more likely to respond and get the conversation started. Even if they are not the person you’d like to interact with in the end, they’ll most likely get you where you need to go.

Here’s a different framework, that is useful, as well: “Is this person spending a considerable amount of time in front of their computers at work?” Folks that spend a lot of time at their desks are more likely to respond to your incoming emails. It’s one of the reasons you’ll undoubtedly have more luck in engaging with folks with office jobs versus local merchants, for example. Local business owners are more than likely going to be knee-deep in operations throughout the day, and away from their computers. The average office worker is going to have more screen time, and thus more opportunity to process and respond to email.

It was a lesson I learned the hard way, when selling a real-time mobile offers solution to local mom and pop shops in San Francisco back in 2011. I had co-founded BeThere and was eager to get our product in the hands of location merchants. It became quickly apparent to us that getting to them through email was going to be close to impossible. They weren’t responding to our emails. We started calling them and showing up at their businesses. It was a game changer. We were able finally engage them around our value propositions. And we quickly signed up 30 merchants across the city.

Make sure you are ready to scale things up.

This might feel a little bit obvious, but I have worked with companies that either hadn’t defined this Ideal Customer Profile, didn’t have enough sales interactions under their belts, or didn’t have the sales infrastructure (people and tools) to handle the increase in demand that an outbound initiative will provide you. Before you launch massive outbound efforts, you need to make you sure have the following things really bolted down:

1) Ideal Customer Profile: usually it helps to have a clear idea of what your target is, in order to define how you will be approaching them. The Ideal Customer Profile is a central document in informing both lead generation, your sales approach, and even building out your call scripts. This doesn’t mean you have to be 100% correct on it, right off the bat. This profile will be a living/breathing document through your company’s lifetime, and it is sure to evolve over time based on market feedback. Without some semblance of an understanding of who you are trying to get in front of, it will be impossible to build out your outbound efforts.

2) Sales Reps: make sure you have the right number of sales reps to handle the responses from your outbound campaigns. It might sound a little self-evident. But not having those resources in place will actually hurt you a ton. It’s one thing to generate responses from prospects through massive outbound. If you don’t have the reps to handle the engagement you’re getting at the top of the funnel, then your whole initiative is not only wasted, but your brand is hurt by it. Imagine being a prospect. You show an initial interest in a product or service — or at least it’s high level value propositions — only to be abandoned once you initially respond. In order to prevent this from happening, I recommend modeling out your outbound efforts before you even begin. From your model, you’ll be able to see how many introductory calls are generated per week and per month. Depending on your reps’ current workload, you’ll then be able to figure out if you have enough warm bodies to handle the responses from leads.

3) Sales Tools: your sales tech stack is going to be your friend throughout this process. You need to make sure you have the basics in place to meet the upcoming increase in demand. In other words, you’ll need a sturdy CRM (in most cases, I recommend these days), and email marketing software to manage your campaigns (I always recommend for those purposes).

4) Sales Interactions: it is imperative that you have had enough sales interactions with the market so that you have established a few things. One: you are going after the right market. You’ll know pretty quickly in your early sales interactions if folks are interested in what you’ve built. You’ll see them lean in, or hear their excitement over the phone. You’ll feel the pull from the market. Two: you have iterated enough on your Ideal Customer Profile so that you have a rough idea of who you are selling to. Three, you’ve been able to get some semblance of a sales process together.

5) Sales Process: it’s critical that you have a sales process that closes customers. Even if it’s just a couple of trial customers. The process doesn’t need to be optimized, or feel slick. It just needs to have gotten a handful of customers across the goal line. In other words, it just needs to work. Once you have such a method, you’ll feel confident in turning on the firehose that is outbound.

Test send your emails to several different email providers.

Make sure to test your emails by sending them to several email providers (Gmail, Yahoo, Outlook…) before launching your full-blown campaigns. It’s worth the hassle, and you would be surprised how emails might show up differently in different email inboxes. Some of these differences are due to formatting. To solve for this, you might start by removing any formatting before inputting it gradually. Particularly if you’ve cut and pasted something from another document initially.

Although this is sure to feel a bit tedious, you’ll be rewarded by having clean, professional emails delivered to your prospects time and time again. Prospects already have plenty of reasons to rebuff you when you cold email them. Removing any additional excuse not to engage with you will prove beneficial.

Leverage outbound for other channels.

Another non negligible advantage of outbound is that it enables you to test messaging very cheaply. Remember, you’re not paying for ads here, you’re just emailing/dialing up customers. Every interaction is an opportunity to test a new messaging hypothesis very cheaply and immediately. Compared to the cost of buying ads on Facebook or Google, dialing/emailing is cheap. At most, you’re paying a lead generation provider at $1 – $2 per lead and a small monthly fee for email software (I recommend

While ads broadcast very few messages to a broad audience, outbound allows for the testing of many different messages to different segments. On average, the same prospect will be hit by several different messages, when sending out email campaigns. Outbound also allows for a back-and-forth with the prospect, which enables you to zero in on what is and is not working.

That’s why I recommend doing outbound to my clients and other startups. And to do it early in your product release cycle. Once you’ve formed a clear idea as to what kind of messaging resonates with certain audiences, you can actually go ahead and leverage that know-how to your other channels, like ad buys or even PR.


Your email subject line is your pickup line.

Treat it as such. If you’re eyeing a potential mate across the bar, the only thing that matters is your ability to get their attention. Without a conversation starter, you have nothing. You could be the most scintillating conversationalist, the best listener, the most inquisitive mind, the most empathic person on god’s green earth, or the most gorgeous human being. The person whose attention you’re seeking might not find out. Unless you are able to start a conversation and engage with the apple of your eye.

The same applies to outbound. Unless you’re able to grab your prospect’s attention with your subject line, you can’t expound about your product’s benefits, or even ask for a 15-minute introductory call. Your opener earns you that opportunity.

I used to remember thinking along these lines, “Well, the email body has a lot more text in it, than the subject line. That gives me a lot more to work with to convince a prospect to respond to my email.”

Sure, it’s more characters to work with. But unless you get the prospect to actually open your email, thanks to a cleverly-worded subject line, your scintillating email body prose doesn’t even get read. It’s a total waste.

That’s why I recommend that my clients test and iterate on their subject lines early on in their outbound efforts. Without really nailing those, the email body doesn’t even matter. I usually suggest that we budget the first few weeks to really test out subject lines for the overall campaigns. Once we’re comfortable with our open rate — we usually aim to land at 40-50% — we can actually pull up our sleeves and get to work on the email body, whose goal is to get a prospect to respond.

Forget about your product or features. Tailor your message to showcase benefits to your prospect.

This is an age-old sales maxim. You are often told in sales to focus in on what value or benefit your product can deliver, when delivering a pitch or giving a demo.

This is further accentuated when you have a short amount of text to grab your audience’s attention and get them to engage with you. It’s important to lead with the benefit or value right off the bat: both in the email’s subject and body.

With outbound, you have the benefit of choosing your prospect. She has been targeted carefully: you have spent considerable time establishing an Ideal Customer Profile and sourcing the corresponding leads. Take full advantage of this targeting by tailoring your message to your prospect. The thing any good salesperson does is force themselves to walk in their prospect’s shoes.

If you really are able to do that, you’ll realize that the last thing you would ever want to receive is yet another email from a company touting their latest product, service, or feature. Your immediate reaction (and you’d be right) is, “What’s in it for me?” Unless you’re able to answer that question, with clear and succinct benefits/value for your prospect, there is a real chance their eyes will glaze over as they read your email and move on to the next one sitting in their inbox.

At some point in your email, you’ll have make your pitch — in just a few sentences — to entice your prospect. Make sure you do it in a way that is relevant to your target.

You may be tempted to lead with your product’s bells and whistles, like this:

“Our widget is great because it has X, Y, and Z features.”

Instead, adapt it to the decision-maker you are targeting, and tell her why it’s important to her.

“Our widget helps streamline your back-end infrastructure and reduces your overall IT costs. Our customers have seen their IT costs go down by at least 55% per year after integrating it.”

Notice that we transitioned from mentioning features that were part of the widget — a product centric approach — to actual solutions and demonstrated value for the prospect — a customer-centric approach. The dynamic is morphed: the prospect goes from feeling completely disconnected and unconcerned about the widget to immediately seeing value in it. It matters to her now. You’ve given her the “Why” she should care. And you have even sprinkled in some social proof for good measure. Customers have already been delivered the value. Why don’t you join their ranks and reduce your costs, too? Finally, adding metrics which you have already garnered — in our case a minimum cost reduction of 55% — adds a lot of credibility to your claims. It’s the impartial, indisputable data that supports your assertions.


Write to a friend.

It can be very tempting to expound on the benefits of your product or service in the first email. What you’ll lose when you do this, however, is your prospect’s full attention. They will get lost in a big email and tune you out.

Remember: your only goal with cold emails is to generate interest and book an initial introductory call. All of the selling doesn’t need to happen right then. All you need to do is pique the prospect’s interest and generate a favorable response from her.

With that in mind comes the following piece of advice, that was initially delivered to me by Conor. In giving me feedback on some email copy, he once told me, “Your email feels sales-y. You would never start an email to a friend like this. You would start with something like this….”

Hey Paul – I thought you’d be interested in hearing how the Best Buy of France {{insert stats}} with a cool new feature that tracks user behavior online and offline, right from the POS.

If you’re interested, let me know and I’ll send over more info about it.


The lesson was clear: make things less formal and more colloquial. I had made the mistake of being overly polite and formal. I had to be more direct and to the point. Since receiving Conor’s advice, my response rate has gone up substantially. My prospects must feel less sold to. And they must feel like I am getting to the point, with less throat clearing, nor exchanging unnecessary pleasantries.


Don’t be afraid to try far-out ideas.

Let’s face it: we are all bombarded by messages all day long. We’re pitched numerous products, and asked to respond to numerous branding messages. Impressions hit our retinas a record clip from sunrise to sunset. It’s a surprise our neurotransmitters aren’t completely shot by the time we get to our lunch hour on weekdays. To break through, it’s important to separate yourself from the pack. And at times, that means pushing the envelope a little bit.

I would highly encourage you be as creative as you can, and embracing as many crazy ideas as you can. As we’ve seen above, unless you engage with your prospect, there is no way to start a meaningful conversation. And as you’ll see, some of the zaniest ideas happen to be the most successful when it comes to outbound.

One of the most success emails we’ve ever sent out has been the simplest. It works so well that I have used it in virtually all outbound campaigns I have built since my former colleague Chris Fitzgerald suggested it when we were at Whitetruffle. It consists of making your first follow-up email in your email campaign —  usually your 2nd email — the following:

Subject Line: email


Did you get my email?


Yes, that simple. And the results are off-the-charts. It usually got us the best response rates of any email we would send out in campaigns that could be 6 or 7 emails long. It probably tugged at people’s need to not miss out on anything, while also removing any “pitching” from the conversation.

Sent from my iPhone

Another wild idea that I heard works really well is courtesy of Steli Efti and the folks at using the “Sent from my iPhone” at the bottom of your email copy. Much in the same line as making your emails plain text and unsophisticated from a graphical perspective, this removes all formality from the exchange and makes the email feel both personal and casual. Recipients feel they are getting something from an actual human being and not an automated email from a profit-driving corporation trying to create separation between them and their cash.  

This next idea was graciously contributed recently by my close friend Austin Gunter. As you’ll see from the email exchange (screenshot below), the sales rep from LeadGenius used a simple trick to get Austin’s attention. In one of his follow-up emails — more than likely in an automated email campaign — the rep actually pretends to have forgotten to send an important case study, and proceeds to email it over. This creates the illusion of spontaneity and humanity behind the message. Austin wasn’t yet another nameless prospect that was being bombarded by massive email campaigns. He had been precisely targeted and vetted as a worthy target for LeadGenius and a sales rep had taken the time to personally write him. When Austin asks him about his gimmick, the rep readily admits that it has proven successful at increasing response rates from prospects.

This next one came to me recently while working with a client. I had sent a response to an inbound lead requesting a quick introductory call. It had taken a while for us to address this lead — we had been flooded with inbound interest — and the prospect responded that they didn’t remember having entered their info in the online demo request form. He went on to ask me when and where he had entered the information. I responded with my client’s online demo request URL. To which the prospect responded that “either this was the most awesome outbound tactic ever or that I’ve completely forgot about reaching out.”

The prospect had forgotten he had reached out. But he served up a new outbound tactic idea. If you have an inbound online submission form, you can pretend like your outbound prospect had reached out initially. It will give the impression that you weren’t the one doing the cold outreach, but that your cold prospect was the one that had reached out. The prospect consequently feels invested in your cause and is most likely going to feel like they need to engage with you.

All of these ideas can be embraced and leveraged by sales and marketing teams. I usually encourage folks I work with to really push themselves creatively. We don’t usually censor ourselves in any way, until we have a good set of zany ideas to work with. Then, you can spend the time to scrutinize each idea and decide on whether or not it has legs. The other factor that must be evaluated is the comfort level of the team and company in employing certain tactics. I have seen companies that immediately feel uncomfortable when using any tactic that might feel like it’s on the edge. I have also worked with teams that have embraced the old Raiders’ motto of “Just Win, Baby”: they were ready to do a lot of things to get their foot in the door, and get conversations started. I am not here to make judgments. I think it’s important to highlight the tactics and ideas that have worked and let folks decide on whether or not they should utilize them.

With that said, I’d invite you to be as creative as possible when doing outbound. You’ll get rewarded for it. Prospects have gotten more calloused and desensitized about receiving messages from drip campaigns and automated email marketing. I had one prospect just a couple of days ago write back to me, “I’ll answer that if you prove you’re a real person”. If you spend the time being creative, you’ll find ways to appear more human in your interactions and get better engagement from your prospects. As you scale up your outbound sales, feel free to share some of your insights and ideas with us. You’re sure to land on some nuggets that will benefit us all.

Always Be Listening

We’ve all been seduced by a good sales pitch in movies or in TV series. By the strong close or the moving speech. Michael Douglas as Gordon Gekko convincing Teldar Paper (and us) that Greed is good. Or Alec Baldwin in Glengarry Glen Ross instilling fear to motivate his real estate sales team. Or Jon Hamm as Don Draper delivering another convincing advertising pitch to his clients in Mad Men.

These expressions are about persuading the other side. About winning them over. About getting them to buy you or buy your product or just buy in. You get another human being or a group of them to do what you would want them to do. In the above examples, it’s the force of pure charisma that does the convincing. And we often think of salespeople as charismatic powerhouses that will others into seeing the world the way they do. Because that’s how they’re usually portrayed on film.

However, some of the best salespeople on the planet don’t rely on their capability to overpower. What they’ve cultivated is the ability to listen. And listen well.

Because, without listening, you never earn the opportunity to deliver the pitch.


Corey Myers, a close friend, and one of the best salesmen I know, once told me over lunch, “Sales reps are basically just waiters.”

In social settings, Corey is charming and animated. Some might even say he has an energetic mouth. A short time into our friendship, we scheduled a call to discuss my startup’s tech hiring. Corey was to sell me on his agency filling one or two of our open job reqs. I can remember what I was thinking when I fielded his phone call. I was bracing myself for a lecture from a caffeinated pitchman arguing his way into a new contract. What I got was drastically different.

After exchanging pleasantries, Corey began asking succinct, pointed questions about my young start-up. After each inquiry, he would just shut up. I couldn’t believe Corey wasn’t chewing my ear off. I could barely hear him. I even wondered if he had pressed the “mute” button, on the other end of the phone line. Gradually, I became more engaged in the conversation, as I answered each of his questions. Instead of getting yet another pitch, I had someone on the other end that sounded interested and concerned about my needs.

Imagine yourself selling as a waiter. You approach your prospect with a short inquiry, “Is there anything I can do to help?” or “How can I best help you?” The conversational dynamic shifts. Instead of being the predatory sales guy yelling into the phone, telling the customer what they need, your disposition is quite different. You’re not here to convince. To persuade. To push your agenda. You’re here to help. Who doesn’t want help?

The ability to listen well helps in other realms. In dating, listening gives you an upper hand. Your date is thrilled to be talking. You’re offering your full attention. Your date feels you empathizing, bit by bit. You both start to open up gradually. You’re vulnerable with one another. Closeness and intimacy emerge from this dance. And trust ends up being woven into the relationship.

The same goes with sales.

Asking questions and listening allows you to get to know your customer better. You’re the other party who is paying attention to them, and trying to solve their problems. Your prospect feels understood, and even take care of. All of a sudden, you’ve become very likable.

Now that you’re a likable caretaker to the prospect, and that you have changed the conversational dynamic, you are gradually earning your prospect’s ear. They have gone from protecting themselves from an upcoming pitch to opening up to you about their problems and concerns. Little by little, through attentive listening and natural curiosity about your prospect, you become a trusted confidant.


As you start getting closer to your prospect, they will start spilling the beans about their challenges and concerns. It’s time to dig in. What are their pain points? What keeps them up at night? What preoccupies them as they drive into the office every morning? What potentially threatens their job, and their ability to pay the mortgage? What will earn them their next promotion or year-end bonus? And finally — as a maitre d’ might ask — where and how can you help? And how can you help most effectively?

By understanding your customer’s aches and pains intimately, you will be able to develop a more tailored pitch, when the time comes. It will fit them like a glove and feel less like a pitch and more like a solution or in this case, a panacea to their problems.

We’ve covered how listening will both get you to empathize with your prospect and inform your pitch. Are there any other benefits to keeping your ears open and mind engaged?

There are plenty.

First, you maintain total control of the conversation by asking questions and listening intently. If, at any point, you manage to think that your solution won’t be a fit for a particular prospect, you can politely bow out instead of pushing things any further. It might avoid an expensive trial, or deployment. You can disqualify the prospect fast and avoid deploying further resources into a customer that might make your life difficult over the long haul.

Second: in many instances, your job as a salesperson is to be the eyes and ears of your company in the market. You’re usually one of the first people on the ground. The knowledge you bring back to internal company meetings might end up informing product strategy, marketing, or even recruiting.

By listening carefully, you might get crucial industry information from a prospect. They might tell you about a competitor’s product roadmap, and their plans to develop a new feature which could threaten your business. Or they might alert you to a competitor losing a key executive. Salespeople are relied upon to bring back these important bits of information back to headquarters. That data can shape company strategy at the board level.

Third, you can listen inward. Although I’m a big fan and practitioner of mindfulness, I am talking about listening to what is happening internally at your company. A colleague needs help on a complicated deal. The #1 sales rep on your team is offering tips on dealing with enterprise customers and their last-minute objections. Or a managerial opportunity opens up to lead a sales team of 4 reps. Tuning in to what happens inside the walls of your office building is sure to pay dividends.

We can all become enamored of the strong pitch on the silver screen. There’s something truly alluring about it. It’s okay to be drawn to it. But, what really makes the difference is cultivating the empathy and relationship between the prospect and the sales rep. You don’t hop on the phone for the first time with the right to pitch your prospect. You earn that right over the course of one call (or several calls) by listening to cultivate empathy and to build trust.

The best salesperson is not the one that can best explain the product or service to others. Or the one that gives the best demos. The best salesperson is the one that listens to the prospect, the market, and her surroundings; processes the information, and produces a tailored pitch. On the receiving end, the prospect feels understood, opens up the purse strings, and happily buys the product.

The tone of the relationship is now set: both parties are upbeat and pleased to be in business with one another. That’s an invaluable leg up when onboarding a new customer. It’ll ensure you get the benefit of the doubt from your new client if speed bumps arise as the relationship develops. As a salesperson, there’s no better way to ride into the sunset, as you hand the account off to Customer Success.

12 Lessons in Early Stage SaaS Sales

It was late 2013. And a close friend of mine, the CEO of a seed-stage startup tapped me on the shoulder and handed me the keys to the customer-facing side of the business. I was to launch our new SaaS model, and grow MRR from the ground up.

In short, I was thrust into a role I had zero business being in.

I had never done SaaS sales before. Never mind, launch a new freemium offering, and build a scalable sales process for a largely-unproven product. Armed with modest sales knowledge accumulated over years of partnership business development and a few short-term inside sales stints, I felt like a gladiator on the verge of being thrown to the lions.

Alex Deve, a stellar product guy, had founded and built a sophisticated recruiting platform in Whitetruffle. It was already generating “lumpy” revenue through success fees. We had decided to move to a SaaS model to scale through more reliable subscription revenue. Alex was handing me the responsibility of growing the sales engine of his business, his baby, into something sustainable.

Did he see something in me I hadn’t yet, or was this just a situation where he was tapping the next warm body, as is often the case in fledgling startups? Perhaps it was the trust he and I had developed as peers; when he and I were founding CEOs of our respective start-ups a few years prior. Or maybe it was Alex’s willingness to roll the dice; betting he could transform raw energy into tangible execution.

Over the course of the next 18 months, we were able to grow the company to $1.2MM in ARR. We built a scrappy sales and customer success team, and were able to develop an entire SaaS sales playbook from scratch.

We were learning things every single day over that year and a half. I’ve distilled some of the learnings that stood out. Here are the 12 most salient lessons I garnered (much of them through trial and error) in the intensive crash course that followed our switch to SaaS.

1) For modern industries, forget outbound cold calls.

Early on in building out our outbound efforts, I wanted to prove that we could cold call into businesses and book calls for ourselves. It must have been my old school mentality towards sales. Or maybe, it was just the fact that I was exhilarated by the idea of infiltrating an organization via phone. As a small sales team, we tried a lot of things to in order to get our prospects’ attention over the phone. The problem wasn’t our lack of creativity. (I once responded to a prospect asking me why I had called with, “Because I was lonely.” This, in turn, garnered a laugh from my interlocutor and a few minutes of bought time to make my pitch.) Nobody was picking up the phone. Our connect rates were right around 5%. We were stuck in Voicemail Land.

What learning did we draw from bumping our heads against repetitive voicemail greetings? That it was necessary for us to ask for someone’s time on the phone over email. In modern industries like those we were selling into (tech companies, for the most part), folks have become savvy at shielding themselves from undesired outside calls. The key is to grab their attention in their email inbox, and book phone appointments that way. If you’re selling into industries that haven’t adapted yet, or that are used to receiving a lot of inbound calls, like restaurants or car dealerships, you can still cold call and get people on the horn. For more contemporary businesses, you will more than likely find out that unsolicited calls are just a huge waste of time and resources.

2) It’s never too early to start addressing the top of your funnel.

At Whitetruffle, we were converting our free trials to paying customers at a 55-60% clip. We were also getting more than half the folks we spoke to on 14-day free trials. I was thrilled with the middle portion of our funnel, and our account management efforts. Yet, one thing kept me up at night: I couldn’t manage to fill our calendars with calls.

It wasn’t until we figured out the right mix of cold email outreach campaigns, calling on existing customers, upgrading free companies, and obtaining reliable referrals, that we hit our stride from a revenue and revenue growth perspective. As the person responsible for revenue, filling the top of the funnel was an obsession for months until we reached that point. The earlier you address the issue, the sooner your sales machine is humming. And that humming will be the sweetest sound rocking you to sleep every night….

3) Hire a new rep (or a couple of reps, as is usually recommended) only when you have reached capacity yourself. Or at least 80% of it.

When you’re the first sales hire, there is a temptation to want company. Sales feeds on competitive camaraderie. You find yourself hitting the phones and doing well yourself, but you don’t really have any teammates to share your successes with. Or someone to confide in when a call has gone South. It can be feel like a lonely existence when you are the company’s sole point man in sales. But you must resist the temptation to hire until you reach capacity, or close to it.

This will accomplish several things. One, it will allow you to build the beginnings of a sales process, you can then teach to your sales hires.

Second, it will allow you to get a loose approximation on what capacity is for any sales rep. For example, you will know how many calls per day you can handle at most.

Third, you will get a good feel for the productivity odds and ends; like how much time you might need in between calls to properly enter the previous call’s notes into your CRM.

Lastly, and most importantly, it prevents you from hiring someone without having a clear understanding of how to sell the product, or without having an idea about how to generate opportunities.

4) Push for annual contracts early and often.




One of my great regrets at Whitetruffle is not pushing for annual contracts more strongly. Recruiting is a very seasonal business. We knew, for instance, that January and September were very strong months for us, and for the recruiting industry as a whole. Folks hire a lot during those periods, and need a sourcing tool like ours to meet with technical talent. November and December tend to be on the quieter side. Activity on the platform would drop on those months. Customers would naturally flock to us in high recruiting periods and hibernate during quiet months.

We had larger enterprise customers who needed to source year-round for a large selection of tech roles. Those companies were happy to pay us a hefty monthly fee, for a steady stream of qualified tech candidates.

Our smaller customers, on the other hand — folks that might only have a couple of tech job reqs open at any one time — the monthly fee we charged was meaningful. It might not make sense to pay it if they were not actively hiring. Those customers had a high risk of churning.

In order to combat the cyclical nature of the business, we used to evangelize the “Always Be Sourcing” motto to internal recruiters. Even if you weren’t currently hiring, there was a strong argument to source nonetheless. The quieter times gave you an opportunity to develop an extensive candidate network by continually sourcing, and getting to know your candidates more intimately. If you knew your candidates’ motivations, desires, ambitions well in advance, you could close them over a phone call, once you were indeed hiring. That thinking only worked part of the time, however. Some internal recruiting organizations saw the value in being proactive. A good chunk regrettably decided to let human nature take over. They stuck to their guns and used us on an as-needed basis. I’m 100% convinced annual contracts could have mitigated churn in those instances.

5) Find ways to control the sale.

One of the big lessons I learned early on was that I needed to control the way the sale was going to unfold. We had decided to structure our SaaS offering with a 14-day free trial that was activated by entering in credit card information. I had been advised that we perhaps didn’t need to demo the product by one of our founders. “This isn’t an enterprise sale”, he had told me. With that in mind, I started chatting with prospects on an introductory call. I qualified the prospect and got them excited about the free trial. Folks generally sounded enthused on other end of the line when I spoke to them on the intro call. Few companies could refuse the high value propositions we peddled: access to more software engineers.

When I sensed they were excited about the product, I naively told them to just get started with a free trial, and that I would follow-up via email with additional information. Can you guess what ended up happening?

Many of the prospects got lost in the ether and never ended up signing up with us. I was initially dumbfounded. All of these folks had shown a lot of buying signals on our calls. They clearly needed software engineers. And fast. Yet, they didn’t manage to budget the few minutes required to sign-up for a free trial.

I needed to find a way to institute a forcing function to get them to do so. I pondered the question for a while. I was going to have to lead the horse to water. But how? After a few days of mulling it over, I instituted a call that was going to act as a forcing function. The call was going to be pitched as an “Account Optimization Call”, in order to “properly get you set-up on your new premium account”. In exchange for a full product walk through, and a detailed explanation of the platform’s bells and whistles, I was making sure the caller would enter in their CC info and start their 14-day free trial. Once I instituted this Account Optimization Call, we rarely lost any interested folks. And we didn’t need to spend any money on screen sharing software. Folks would unlock their free trial of the premium product and I would take them through it with my admin access. Prospects were happy to get a full product tour, so they could leverage the premium side of Whitetruffle to its utmost and hit the ground running on their free trial.

I was thrilled to lock them into a free trial with a credit card to charge after the 14 days were over. Still, about a third of my Account Optimization calls started with folks that hadn’t yet started their free trials. They were apologetic on the phone, “I’m sorry, Paul, I haven’t had the chance to move things along.”  I’d respond, “No worries, whatsoever. We’ve budgeted thirty minutes for this call. We’ve got more than enough time. I can hold, if you need time to enter in your credit card information.”

6) Train your reps in Save Opportunities.      


In SaaS, the value of signing on a new customer is just the same as saving a customer that has been threatening to leave you. Yet, very little training is usually included in the Sales Playbook, that will show you how to save customers. Sales playbooks are usually geared towards customer acquisition. Very few playbooks actually tackle the issue of saving accounts that are on the verge of leaving you. Save opportunities are challenges in their own right. They take a high level of empathy and attentiveness. And although you can have folks that are naturally gifted at saving accounts, it is something you can teach, with the appropriate patience and training. The key is budgeting the time in your training to get your sales reps up to speed in that department.

The term has been getting plenty of press, but it bears repeating here. Empathy is a major component of saving sales opportunities. If the customer feels like you feel her pain, she is more apt to give you another chance. It’s about teaching your reps to be engaged listeners. The first step to instill in any rep faced with a  save opportunity is to find the cause or root for the disappointment. As your reps are getting the elements of the customer’s dissatisfaction, train your reps not to respond immediately with solutions. Doing so, will make the customer feel she is not being heard. And it might even sound defensive. Have them pay attention to the customer and make them feel cared for. It is crucial to take copious notes, during this process. This will enable you to respond to each point once you’ve taken in all of the customer’s gripes and perhaps present ways in which you can make the service better for them in the future.

During the save opportunity, the rep’s job is not to convince the customer that they have the best product or solution on the planet. The key is convincing them to stick with you a little while longer so you can turn the corner together. A strong sell at this critical juncture will feel forced and will sound dissonant to your customer. Don’t forget: your customer has the intention to leave the service. The rep’s mission is to paint a picture as to why things will turn around. Obviously, this is a great place to conjure up any best practices, particularly if they haven’t been used during the time where the service didn’t live up to expectations. For example, at Whitetruffle, when companies weren’t getting much love or interest from candidates, we offered to help them beautify their profiles. This was our equivalent of a dating coach giving a client a much-needed makeover. “It looks like you haven’t included funds raised in your company profile. While we understand that some companies are not comfortable publishing this information, companies that do actually get more positive responses from candidates. It gives them the reassurance that you’ll be around for the long haul.”

Before long, you’ll start noticing that it’s easier to save an account than to close a new one. And your churn rate will decrease accordingly.

7) Hire a rep with early stage experience.

You might see “Salesforce” or “Oracle” on a CV and think it guarantees a candidate has the right chops, because she has been through a sales powerhouse. These are mental shortcuts used by recruiters when evaluating resumes. What are brands if anything but mental shortcuts? When you go to a McDonald’s worldwide, you know exactly what you are getting, whether you order your Big Mac in Paris, Tokyo, or DesMoines. Same goes with Starbucks. Or Louis Vuitton. Brands exist to reassure us, that yes, we will be getting what we expect. Brands, in these instances, represent an implicit contract between the consumer and the business; a guarantor of sorts, for the standards set by the business.

With sales rep CVs, “Salesforce” or “Oracle” are brands as well. They tell the recruiter that the salesperson in question has been able to withstand the training at these sales-based organizations, and has more than likely learned some fundamental sales skills. The problem is they don’t address a set of skills that are unique to early stage SaaS sales. Folks with large organization sales experience are used to being part of large scale processes. They are used to things being handed to them.

Like getting leads or opportunities handed to them on a daily basis.

Within those large companies, a sales rep’s only worry is about taking those leads or opportunities and moving them forward: from qualification to close.

Working at an early stage SaaS company means you’ll get a basic process — if you’re lucky — and little-to-no hand-holding. A lot of times, early stage existence is about making something happen out of nothing, or devising ways that will get you through adversity. It is about taking on a new initiative and running with it. Or picking up a broken process and fixing it.

Nothing about working at large sales organizations will teach you these skills or inner dispositions. That’s why I would rather pick someone that has worked in the early stage startup world than someone who has worked within proven sales organizations. I want someone who thrives in chaos, who takes initiative, and has the wherewithal to pick things up that are broken and fixes them without asking for my permission. Or begs for forgiveness later.

For early sales hires in SaaS startups, I will always favor folks that have, for example, done partnership business development work in early stage startups over someone who has done SaaS sales at a large company.

8) Make sure data is being entered properly into your CRM.

This one seems pretty obvious but it bears repeating in the case of early stage startups. We have all heard of the rogue sales rep who closes a lot of deals, but doesn’t enter information into the company’s CRM. This person ends up holding on to his job only based on his success on the ultimate sales scorecard: substantial revenue generated for the company. That’s because data entry is such an integral part of a sales rep’s job.

You might ask why? Shouldn’t the salesperson worry exclusively about closing deals and bringing in revenue? The answer: a resounding “no”. And here’s why. Data entered into a CRM isn’t just meant to sit there. It is meant to be leveraged in two ways. First, the entire sales organization needs to know how a particular deal is going. A sales manager needs to be able to step in and help out the rep, if he reaches a point of friction. A fellow rep needs to be able to look into an account to make sure she isn’t stepping into any toes when selling to a different department within the same company.

Second, and most importantly, all data entered by individual sales reps is aggregated into analytics leveraged by the Head of Sales and other executives to steer the overall business. If data is not entered, or not entered properly, then the Head of Sales and other executives are left steering the business blindfolded. In high velocity sales models — like the one developed at Whitetruffle — it is critical to get a steady stream of clean data as it is used to make adjustments to the business on a weekly basis.

At a large organization, if one of your 1,000 sales people doesn’t enter data, it might not affect the way you do business very much. At an early stage start-up, if one of your two sales reps isn’t entering data in your CRM, you are losing half of the data you are relying on to make business decisions.

Losing such a data input simply isn’t negotiable. If one of your early stage reps isn’t entering data in properly, it threatens the business, and should call his or her employment into question.

9) Don’t bother with Salesforce until you have a basic sales process in place.

Some people will tell you that Salesforce needs to be implemented once you’re ready to launch your product. That’s inaccurate. At Whitetruffle, we didn’t migrate to Salesforce until we had passed the $1MM ARR plateau. And I don’t think it slowed down our growth one bit.

Let’s face it, Salesforce is the dominant CRM for two main reasons. One, it provides a rich app ecosystem, for add-on bells and whistles to the cloud platform. Two, once set-up properly, the data reporting can be a very powerful function.

At Whitetruffle, getting the rich analytics up-and-running enabled us to nail our outbound cold emailing initiative, for example. What folks rarely talk about is the amount of front-loaded work necessary to set-up Salesforce properly. At Whitetruffle, we called upon a team of consultants that helped us set-up our instance. And I was investing a ton of time as well.

This time investment is significant, and if you aren’t generating revenue already that’s the only thing you should be focused on. Your first customers are your toughest to close. It’s likely that all of your energies and brain power will be needed in getting those first clients over the line.

I would recommend implementing Salesforce once you’ve got a basic sales process in place, and that you’re ready to invest the required time and energy. There are plenty of SMB CRMs (, RelateIQ, BaseCRM) that will allow you to hit the ground running when you first launch your product.

Additionally, if you haphazardly set up Salesforce early, at some point it will cost you months to fix what you set up as broken in those early days, just like engineering technical debt.

10) Select your signals for churn. And start tracking them very early.

The most beautiful thing about SaaS is that — if you keep churn under control (and that can be a big “if ” for some) — you are constantly building revenue. Sound account management therefore should be about controlling and minimizing churn.

Let’s borrow liberally from early stage product development.

The discipline stipulates that you are should uncover the metrics that drive your product. It’s important to lock into 2-3 metrics that will be the index for the overall health and growth of your product. Those metrics are monitored very closely and your product team will be judged on its ability to deliver against them. In early stage product development, you might not lock into the right metrics right off the bat. It might take a couple of stabs, and some iteration before you get just the right data to monitor on a continual basis. The same pattern applies for account management and churn mitigation.

At Whitetruffle, we started looking at very simple metrics. At first, we would track things like “Logins over last 30 days” or “Matches processed over last 30 days”. To us, these were good early signs of engagement. As we got more sophisticated, we realized that a good indicator for the experience employers were having on the platform was the number of intros they would get to candidates over time. We started looking at monthly intros, and then realized that this time frame was too wide. Customers were likely to drop off if they didn’t get any intros on a weekly basis. So “Intros last 7 days” became a much more relevant metric. Monitoring it allowed us to be more reactive with our customers. A lack of intros over 7 days would send us a red flag. Our account managers would reach out to the customer in question, and ask if everything was going well for them. A lot of times, this opened up a productive dialog with a customer; a conversation that would enable us to better serve them in the long term.

11) Your identified Decision Maker might not be the best way into organizations.

Whitetruffle is a sourcing tool used by internal recruiters to generate tech candidate flow at the top of their recruiting funnel. It doesn’t take much brain power to surmise that you should be selling to the Head of Recruiting. Yet, talking to these Recruiting Czars didn’t end up being our preferred way into organizations. If we had our druthers, we would rather go through the CTO or VP Engineering. Why is that?

There are a few reasons. First, CTOs were seduced intellectually by Whitetruffle. We were solving a very human problem — matching the right companies to the candidates most likely to want to talk to them — with an algorithm that looked at 50+ core signals. That kind of problem solving appealed to the vibrant minds leading tech teams.

Second, CTOs were the most likely affected by a lack of sourcing. When a CTO commits to product deliverables, it is his derriere that is on the line if he can’t deliver on time. Delivery on product milestones is usually a function of technical team size. And Whitetruffle, as a sourcing tool, was (rightly) viewed as a catalyst for technical team growth.

Third, CTOs carry a lot of clout within a tech company. We noticed that once we had buy-in from them on our solution, adoption within internal recruiting was immediate and seamless.

The fact of the matter remains that we talked to both Heads of Recruiting and VPEs/CTOs. And both were effective ways in. But, if we had our choice, the tech leader was the person we would want to get in front of, as it would expedite the sales process.

The overriding lesson is this: before locking into one way into an organization, be as broad and open-minded as possible about how you might infiltrate the fortress. By testing different ways in, and chatting with a varied group of decision-makers, you might stumble on an easier way in to rescue the princess. And you won’t be as spent when you get to her.


12) Set expectations for what represents success (particularly during the free trial period).

In sales, you are taught the importance of setting expectations. Without doing so, you run the risk of having a prospect complain about your service, while you were delivering on the initial promise. Sometimes prospects don’t even know why they aren’t satisfied with you. They will make excuses and might not even be able to articulate why they aren’t continuing to work with you. However, if you make the expectations clear and have them agree to them before getting started, there is no denying them later on.

And guess what? Even if you happen to be a bit shy of them, they might decide to work with you, because you fell short of expectations by a very small amount.

Now, how did we go about doing that at Whitetruffle? In our Account Optimization call, we would tell prospects they could expect 3-4 intros to candidates during the 14-day free trial. It’s a mark we were pretty sure to clear. It therefore positioned our free trial offering favorably in the customer’s eyes. And it contributed to our success in converting our free trials to paying customers at a very high clip: 55-60% of the time.

Eleanor Roosevelt famously said, “Learn from the mistakes of others. You can’t live long enough to make them all yourself.” During my time at Whitetruffle, I felt like I was operating from within a sales lab. I was afforded the freedom to run experiments — large and small, conventional and off-the-wall — in order to grow revenue. We made plenty of mistakes in building out our sales model. And we learned a ton from those errors. Hopefully, you’ve been able learn from some of my blunders. Over time, you’ll make a few of your own. And as the former first lady suggested, until we find the secret to eternal life, we’ll invariably be looking to you for the learnings from those faux pas.

Federer’s Sacred Number

There’s something poetic about Roger Federer. It’s undeniable. The man glides on the court; deftly melding pinpoint accuracy with grace and velocity. Several times per match, Roger reminds us that tennis is a sport that approaches art. He has elicited prose from prolific wordsmiths like David Foster Wallace. It’s perhaps why so many of us have become attached to him beyond reason. For those of us that bow to the Swiss Maestro, one question has been obsessing us over the past couple of years: is his Slam record of 17 safe?

With Federer and Nadal facing off in Sunday’s Aussie Open final, the question has never been fraught with so much meaning. The Majorcan stands to win his 15th Major, if he’s able to beat the man from Basel, in their first Slam final encounter in 6 years. That would move Nadal past Sampras on the careers Slams list, and would put him two back from Rog. Federer could hoist his 18th Grand Slam singles trophy, and first since Wimbledon 2012. This would thwart Roger’s biggest rival and widen the gap between his trophy case and that of the Spaniard.

If we are to look at the biggest threats to Roger’s sacred Slam record, two names stand out from the rest: Nadal and Djokovic. The aforementioned Rafa Nadal is 30 years old and stands at 14 singles titles (3 behind Federer as I’m writing this) at Majors. He hasn’t won a Slam since Roland Garros in 2014. And that was the last Slam final he reached, until Sunday’s Aussie Open against Federer. That’s close to 3 years without competing on the final Sunday of any Major. Nole Djokovic has collected 12 Grand Slam singles titles, and will turn 30 in May, just before Roland Garros kicks off. After a blistering 2 years that saw him capture 5 Slams, and hold all 4 trophies at one time, the Serb has slipped up and hasn’t won a Slam since the 2016 French Open. That includes two early round exits; a third round sendoff at SW19 last summer, and a second round loss this year Down Under. Rumors have been swirling about his personal life. Astute tennis observers have wondered if he has lost his mojo for good.


If Nadal and Djokovic are the greatest threat to Roger’s record, and both of them have been slowing down as they have neared 30, the question we should ask ourselves is: at what clip have men in their 30’s won Slams historically?

In the Open Era (1968-today), only 19 Slams have been won by players after turning 30. Agassi, long considered a late bloomer, who hadn’t logged a lot of miles in the early portion of his career, only won 2 Slams after turning 30. Rosewall and Laver, who had a lot of tread left on their tires, are the record-holders for Slam wins after 30. Each Aussie won 4 after crossing that age barrier. Another thing to note: there has been a slow-down in Slam Winners after 30 in recent decades. From ’68 to ’77, 11 Slams were won by men who were over 30 years of age. From ’78 through ’87, only 2 Majors were won by men over 30. The ’88 through ’97 decade saw 1 Slam won by a 30+ year-old. ’98 through ’07 brought us 4 Slam trophies hoisted aloft by men 30 and over. And finally ’08 through today has delivered one Grand Slam taken home by a man having reached the age of 30. That’s an 11-to-2-to-1-to-4-to-1 progression over the last 5 decades.

Granted, there is the remainder of 2017 left to tabulate for the latest decade. And Sunday will be the 5th time two 30 year olds will face off with a Slam at stake. That guarantees we will have at least 2 Slams won in this decade and perhaps more. The old guard of 30 year-olds which includes Nadal, Wawrinka, and Federer are all threats at Majors. And both Murray and Djokovic will turn 30 in May before the French Open begins. That’s quite a cavalcade of trentenaires capable of bagging a couple more Slams with 3 remaining on the calendar. One might even say that of the 3 majors remaining, there’s a greater chance those are won by that group men in their 30’s than the rest of the field.

There’s been a theory peddled in recent years in tennis that better nutrition, a more rigorous fitness regimen, better exercise science, and even increased mindfulness have enabled top players to remain at the top of the game at a more advanced age. Perhaps it has. But as we’ve seen in our analysis of 30+ players, it hasn’t necessarily translated to more Slam trophies on the Men’s side. At least not yet. All 4 Slams this year would have to be won by men in their 30’s for there to be growth (5, up from 4) from the previous decade in Slams won by 30+ year old men.

Even if there is a bit more longevity in the men’s game, it is hard to imagine that any player would win 4 more after that age. Ken Rosewall and Rod Laver, the record-holders for Slams post-thirty, played in an era of lesser depth. Today, a poor night’s sleep or a minor indigestion for a Top 5 player could have him slip up enough to lose against a player ranked 100 spots below him. It happens all the time. And that doesn’t even factor in a group of younger players who are all considered Grand Slam material. Gentlemen like Raonic, Nishikori, Alexander Zverev, and Dimitrov have been knocking at the door, and are likely to breakthrough in the coming years. Those are all men capable of snatching a few Grand Slam trophies away from the likes of Djokovic and Nadal. And that’s not counting the proven Major contenders like Murray and Wawrinka who have already crossed the Slam Chasm.


After Sunday’s Australian Open final, Nadal will either sit at his current total of 14, while Federer will have pocketed his 18th, or Nadal will possess 15 Slam trophies while Fed will remain with his record 17. Djokovic, who is probably training at home in Monte Carlo at this hour, will obviously still have 12 Majors. In the event that he wins Down Under, Nadal would need another 2 Slams to equal Federer’s total — assuming Federer doesn’t win any other Slams — and 3 to pass him. Nadal hasn’t been in a Slam final or won one since the 2014 French Open. That’s a drought of close to 3 years. For Rafa to pass Roger, you would have to expect Nadal to win another 3 Slams for the rest of his career, on top of this year’s Aussie, past the age of 30. All while projecting: Roger without another Major win. For Nole to pass King Fed, you would have to expect Djokovic to win another 6 Slams, all after turning 30. While projecting: Rog doesn’t win another Major. That’s a ton to expect from Nole past the age of 30. He would have to win more Majors past 30 than any other man (both current record holders Rosewall and Laver hold 4 after 30), in an era with much greater depth and physicality.

Both scenarios that have Djokovic or Nadal passing Federer in total Grand Slams are highly improbable, if not virtually impossible. They assume unrivaled production from either player after turning 30 years of age, all the while inferring Roger will not add to his Slam trophy case. Yet, the Federer Express has shown us recently, and particularly this fortnight, that he’s able to play the kind of game that will have him threaten at Majors. He could very well capture another Slam or two. Starting with tomorrow.

Lessons from Heartbreak

I am recovering from a breakup with a love of my life. Late January marked the end of a long, and, at times, tumultuous relationship with a woman I loved immensely, and was completely emotionally naked with. She truly meant the world to me. The recent bookend to our love story has been particularly rough.

We’ve all been there. Once a long-term romance is called off, pain inevitably ensues. There’s more than just emotional suffering and mental anguish. There’s a physicality to every breakup. The connective tissue that once held the relationship together is severed and rips a void in the pit of your stomach that feels permanent and irreparable. It feels like a part of your abdomen was ripped out. You’re left wondering if you can ever give yourself fully to a relationship again.  

I’ll be honest: it’s been massively hard. I’ve made it through by giving myself space for things like reflection and sadness. A steady dose of yoga, introspective beach walks, meditation and therapy have helped. And good cries over BB King songs :).  

I’ve taken a lot of time to myself to mourn the failed relationship and figure out what I can draw from it. Lessons need to emerge out of the sadness; learnings I’ll be able to take with me as I move forward. I wanted to learn as much as possible for the sake of my next relationship, so I dug in. I looked back at this recent breakup and those before it and I tried to distill the best insights from past heartache.

Here are a few of these lessons.

I can actually take on too much responsibility.  

“What?!” you say. “Isn’t it good to take responsibility for your actions?” Haven’t we been all taught to do so from a very young age?  And for good reason?  

Yes, these early learnings are in large part incredibly valuable to teach you responsibility.  In a failed relationship, I have learned there is plenty of blame and accountability to spread around. To both parties. When grieving a past relationship, it’s very easy to slip into internal torment of the form “What could I have done differently?”  

One thing I’ve found works well to overcome this issue is to do the parsing exercise of what was on my significant other and what was on me. Be very deliberate. If you need to write things down, so you can see the items before you, don’t hesitate to pull out a pen and paper. Draw a line down the center of the page and start writing the things you take ownership for, and those that should go to your former significant other.  

This will accomplish several things.  

One, it will enable you to take responsibility for the problems you created in the union. You’ll have those to work on between this relationship and into the next one. Two, you will have a set of things that are not “on you” but on your former lover. You’ll notice that there were things you had very little control over, and that the relationship ended for reasons that didn’t fall on your side of the ledger. In the final accounting, you’ll start seeing that it did take two to tango.  And that you were not entirely responsible for the overall health or the ultimate failure of the relationship.

Don’t ignore the red flags.  

There’s the old saying: Love is blind. It is. Without a doubt. Particularly in the honeymoon phase.  The pheromones take hold and we’re smitten with our new partner. He/she can do no wrong. Our minds and body have been taken over, and all you can think about is your lover. It’s a beautiful thing. Yet, the trick is keeping up our awareness while in this love fog. Not doing so puts us at risk of missing any red flags. That means keeping tabs of your feelings, moods or emotions as you start the relationship. Think of your feelings as your navigation system; internal signals telling you things that your mind hasn’t yet fully wrapped itself around.  

If you’re feeling anxiety in the initial stages of a relationship, for example, ask yourself why this is showing up for you. Dig a bit deeper. What is the root cause of my feeling unsettled? What are my feelings telling me? As you start unpacking, you’ll land on nuggets that will prove very beneficial. Maybe your partner isn’t opening up to you as much as you would like, or perhaps not showing up for you. These are things you can now discuss and work on with your lover in an effort to grow closer.

In reflective moments after a relationship has ended, I have looked back only to realize that there were warning signs I had decided to completely ignore. My head was buried in the sand and savoring young love. The sooner I am able to identify the red flags, the faster I can address them. That’s only possible if I keep my emotional radar activated so as to not lose sight of my true North.  

Don’t blame your partner for their blind spots.  

This applies to all relationships, amorous and otherwise. Until you’ve told someone something, the assumption should be that it is out of their awareness and can’t be changed. Your responsibility is to communicate that to them calmly and concisely. If they don’t respond, once you’ve brought the issue to their awareness, then you’ve got a gripe to hold onto. But unless you’ve done your part to bring something up, you shouldn’t expect them to change their behavior.  Because they may not know any better.  

Humans are inherently limited.  

This might seem like an obvious one, but it is the hardest lesson I’ve had to take in the past couple of years. Not only in the personal realm but in the professional realm as well. It’s one belief I had refused to live by for a long time — I’d like to think all of us are capable of improving and forging ahead — but I’ve had to accept that even if you communicate your needs to your significant other, there is no guarantee they can actually fulfill them.  

You realize the person you’re with will continue to fall short, because they don’t presently have the capacity to fulfill your needs and your aspirations for the relationship.

It’s a rough assertion to come to terms with. But it’s also the most liberating thing, if you’re completely able to process it. It will set you free.

In my most recent relationship, I kept thinking certain things would change in my partner. I held onto the belief that certain traits were aspects that could be worked on and worked out through sheer will and determination. But that was my own personal paradigm; a view I was projecting onto my partner and the relationship. I came to the hard conclusion that I did not control all of the variables, nor could I affect all of the change I was desperately looking for.    

Love will reveal who you are.

The great thing about falling in love is that each relationship will teach you a whole lot about yourself. True love makes you incredibly vulnerable.  

It’s like standing in front of a full-sized mirror completely naked. You get a clear reflection of who you are as a partner. You’re able to discern your soft spots, your weaknesses and your calloused edges. Each union imparts additional self-knowledge. Each new lover gives you a new reflection of yourself and prompts you to grow.  

As you get more acquainted with your needs, you grow more finely attuned to those that will fulfill them. You’ll get back out on the dating scene with a more refined sense of who might be your ideal mate.  

Your tastes will evolve.  

You might have liked the sizzle and forgotten about the steak. Next time around, you’ll make sure there is substance to your love. You might have fallen for the alpha chick, only to realize that she not might have been the ideal partner in raising children. Or maybe it was the bad boy who was exciting but couldn’t provide you with any stability. All of these realizations come from confronting yourself to a new relationship and to your needs. If you are to look back at your relationship history, you are sure to find an evolution in tastes. You’ve tried people on for size. As you grow older and acquire self-knowledge, you are more likely to find someone that fits snuggly to your needs.

Anger is healthy to hold onto (in the beginning).  

We’re often told that anger can be toxic. That it can eat at you. That it will hold back. It’s often demonized as a source of violence or torment. Anger is also a powerful force. It is an emotion that makes you feel in control. In the driver’s seat. One of the issues we all face when trying to leave a relationship is that we’re held back by its gravity. We’re still entangled by the attachment we have with our partner. Anger, during separation, plays the important role of catalyst.  

Think of anger as the spare rockets on the space shuttle and your relationship as Planet Earth.  The rockets are critical to get you disentangled from your attachment and into orbit.  But, in the end, once clearly separated from the planet and in outer space, the goal is to drop your spare rockets in order to achieve control and serenity. Ideally, you want to be able to look back at your relationship and your ex with tenderness and empathy. Just as you might look back at Planet Earth from the space shuttle and admire its sheer beauty.

Spare Rockets Pic

Remorse over regrets.  

The French have the following saying, “It’s better to live with remorse than with regrets.” One of the hardest things to deal with in love is knowing that you didn’t quite give it your all, or that you could have done things differently. Unfinished business can gnaw at you, as you think back to “what could have been” in a relationship where you believe you could have given more.

I have found that with some relationships, it’s important (if not critical) to burn through them entirely. Till the bitter end.

In my recent relationship, I had a vision for a beautiful place we could get to, yet I didn’t quite think we had done everything in our power to get there. I wanted to know that I had left it all out on the floor and exhausted every possible avenue. If the relationship doesn’t pan out, what you’re essentially doing is buying yourself future peace of mind, and eliminating regret from the equation. And that’s worth hours of sleep and tranquility that breakups have the power to steal from us.  

Past relationships are lifelong assets.  

There has to be a bright side to how catastrophic breakups feel to us. The silver lining, I’ve found, is that failed relationships are lifelong assets. I’ll be able to look back at each individual relationship as I continue to go through life and keep drawing lessons from it.

Interestingly enough, the more painful the relationship, the richer it will be in lessons. Several years ago, I had a 3.5 year relationship with a lovely woman to whom I could have gotten engaged. We ended up separating after living together for over 18 months. It felt like a mini divorce, as we disassembled our life together and moved out of our shared one bedroom in San Francisco’s marina district. I was initially destroyed and it took me close to a year to recover. But this one relationship has been a treasure trove of lessons when it comes to my love life. The learnings keep on coming over 4 years after our separation.

First, I came to realize that I didn’t see myself evolving with her long term. I’m now convinced that our paths would have diverged over time. It wasn’t till years later that this nugget emerged and that I was able to articulate it. When we separated, I wasn’t fully aware that our likely evolution would have us grow apart.

Second, I needed someone that was willing to work hard on a relationship. I had offered to seek some outside help when our relationship was falling apart, and she had refused. I came to realize that I couldn’t be with someone that wasn’t willing put in the hard yards for a relationship. Over several decades of marriage, bumps in the road are sure to come up. I became acutely aware I needed to believe that the person I was with could be my partner, roll up their sleeves, and weather the tough times side by side with me.

Next time you think you’ve hit rock bottom, as you’re trying to pull yourself together post-breakup, try to remind yourself that the journey you just went through will provide you with some invaluable gems of insight. It may feel like small consolation at the time, but as you heal, and later on, as you look back, you’ll realize that everything you just went through — if carefully examined — will prepare you for your next romantic endeavor.