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 paul@gassee.com to schedule a time. Be well and stay safe!

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 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.


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 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 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.