How to take your outbound sales to the next level

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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 Close.io these days), and email marketing software to manage your campaigns (I always recommend Outreach.io 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 Outreach.io).

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.

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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.

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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 with 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.

Thanks,
Conor

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.

 

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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

[FirstName]:

Did you get my email?

Paul

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 Close.io: 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 this 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 all of us.

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Always Be Listening

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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.

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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.

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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

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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.

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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.      

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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 (Close.io, 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.

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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

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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.

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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.

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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 :).  

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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.