“My product is not ready to sell.”

“Our website is not yet optimized for inbound traffic.” 

“I’m not sure we have the capacity to take on more than three customers per month right now. What if we get more interest than just that?” 

“We’re devoting our energies to nailing product-led sales right now. We’ll do outbound if this doesn’t pan out.” (This one has become a personal favorite of mine. It’s gotten trendy.)

All excuses not to get started with your outbound sales. I tell founders that it’s never too early to start working on your outbound sales. And frankly, I’d love to be able to shout it over the rooftops. 

Founders don’t get started with outbound early enough.

Even when doing customer development, it’s helpful to unlock the motion that will get you in front of customers in a reliable way. Predictability in getting in front of customers is what’s called “Message-Market-Fit”. It’s the idea that you need to unlock the right message that will have your prospect respond with interest in having a first conversation with you. An arduous problem to solve; it can take some startups 6 months or more to unlock it. Getting started earlier rather than later is very much recommended. 

Message Market Fit is a crucial part of Product Market Fit but usually doesn’t the love it deserves from founders, I’ve found. Technical/product founders usually retreat to their strengths; to their product caves to code new features, when things aren’t lining up. Sometimes it’s not a product problem whatsoever. It’s the way the product is explained to the market. Instead of cranking out new features, we should be developing new copy variations to test in the market.

You could be a few months away from launching your product, and I would start setting up outbound experiments. You should go out with campaigns so you can iterate on those as the early results come in. I often recommend to my clients they start their outbound motion before starting product development. At the idea stage, getting in front of prospects repeatably without relying on your network is the best way to get unbiased validation of your product vision. That kind of feedback is invaluable and in effect greatly de-risks your startup early on. 

Unfortunately, I meet and work with founders often who don’t go through this risk reduction phase and rush into building product. Their customer development either is nonexistent or not rigorous enough and it becomes harder to find product-market fit when they are finally ready to go to market.

All of this to say that founders rarely start this exercise early enough. Even if the payoff is huge in product market fit risk reduction and revenue growth. At Whitetruffle, for example, where I ran sales, before dedicating myself to coaching startups, it took us 6 months to fully build out our automated outbound email initiative. It became our largest acquisition channel, responsible for 50% of our net new MRR every month.

“We’ve tried outbound but it didn’t work”, founders will tell me when we first meet. 

My next question usually is, “Great, how many campaigns did you send out?” 

“Uhmmm. 8 or 9, I think. But we didn’t book any calls from them. So we stopped.”

Founders give up on outbound after a few campaigns appear to fail.

Let’s start here. Sending out 8 or 10 or even 20 outbound email campaigns is not considered “giving automated email outbound a fair shake”. You have to give this sort of initiative at least 4 months of sending 4 to 6 campaigns out per week. 

Most founders don’t know the barometers of success when it comes to conducting outbound (more of that later). And then, they usually don’t possess the required rigor, grit, and patience to pull it off. When I tell them they need to apply themselves for that long, I usually get raised eyebrows, “Really? It can take that long?” 

Of course. Finding message-market fit is incredibly difficult. There are numerous permutations and formulations to try. You should commit to the long haul if you want your startup to make it.

Man, I see this one all too often as well. And it comes from a beautiful place for the most part. Founders have been gestating their products for 12 to 24 months and are now proud to show them off to the world. 

Just like joyful parents, they might exclaim, “Our app’s carefully crafted accounting module will allow you to spend 50% less time running numbers. You’ll be home for supper, even during the busy season.” While I love this pride – it’s one of the best parts of working with founders – it doesn’t bring home the bacon. 

When putting outbound copy together, founders lead with their product or service.

Prospects are self-interested busy people (like most human beings). While they might be touched by your enthusiasm for your product from time to time, they’d like to know what’s in it for them at a very core level. There’s an old adage in outbound: you get a lot more from pain than you do from gain. Meaning, lead with the pain point your prospect is dealing with that you can help them eradicate with your solution. It will soften your prospects and allow them to listen to you – and, in many cases, read on. It will feel like you’ve empathically put your arm around them, and told them, “I feel your pain.” Instead of shoving your product down their throats right at the onset of your interaction.

We’ve found this adage to be so true over the years, that we’ve been able to develop or help our clients develop successful copy that is almost entirely pain point-based, with little else.

Something like this:

[FirstName]:

Have you been dealing with [PainPointA]? Has it been particularly stressful for you in the past couple of quarters?

If so, you’re not alone (many others we’ve spoken with have suffered from it) and we should chat. Over the past two years, we’ve developed a solution to [PainPointA].

What times work for you next week to see if we might be able to help?

Cheers,

[SalesRepName]

Notice: all this copy does is mention the pain point, draw out the pain, state that we’ve been developing a product to eradicate it, and invite the reader to a call to see if we might be able to help. There’s no mention of how the solution works and what it actually does (apart from its impact/outcome).

Leading with pain will make your prospect feel respected. And not sold to. It makes them feel like you care about their suffering, as opposed to caring about selling your product. One makes it about you, while the other makes it about them. Now, which one do you think will get them to react more positively at the outset?

 

You’ve been there. 

You’re making one last push to get through your email before shutting down for the day. A subject line catches your attention, “quick question?”. “Catchy, enough…I’ll bite,” you think. 

You peer into the email. The long blocky text overwhelms you. The first line reads, “Hey Jim, I hope this email finds you well. I am reaching out to you because you seemed like the perfect industry expert for me to interact with…” The stench of formality and lazy flattery waft out of your inbox. And you can’t possibly go on.

You rush to close your email client and your MacBook in one fell swoop. Work. Day. Over.

 

Founders write outbound copy that is too lengthy and formal.

This may be the most frequent mistake I see from founders as they start writing outbound copy. Their copy is far too long. And it’s mired in formality. You have to realize a few things that are simple, yet not applied nearly enough. Your recipients are usually highly busy people whose lives you just interrupted with a message. They don’t know you at all. And they’d like to get back to the things they were doing before you barged in on them. Use that inbox interruption wisely. Write crisp copy that leaves them intrigued. Leaving them wanting to have a quick conversation with you. Nobody reads your long emails (well, maybe your mom does). 

As a quick thought exercise, visualize your prospect. Susan is a high-profile CTO at a Series B startup in San Francisco. She was plucked out of her last gig by Andreessen Horowitz, who both recruited her hard and also led the Series A. Her frenetic workdays have her juggling hiring at lightning speed – her VCs have just dropped $45M on the management team’s lap to scale the team – and managing her direct reports. She has an equally ambitious husband – who runs a cleantech startup – two children, and a Labrador at home in Noe Valley. Despite her sturdy support staff, she has very little time for herself while working. When she does go into her downtown SF office three times a week, she steals a glance at her phone on a 20mins break as she waits for her favorite lunch: fish tacos at the food truck downstairs. 

That’s the opening you’ve got, for your outbound email.

When working from home, free time is a rarer occurrence. Her family takes up most of the interstitial time between Zoom meetings or deep work. Only when she’s walking Charlie, the family’s 2-year-old pup, does she sneak in a look at her smartphone. 

Those are the few times you can reach her via email. And her phone – despite being a recent iPhone – has limited visual real estate. 

With those time and space constraints, the point is: you’ve got to make your email count. Keep the email body copy to 4-8 sentences. 

You can easily build that muscle with an exercise our Head of Outbound & Ops Rob has developed over the past couple of years. He initially used it as a forcing function on himself. He then revealed it to me and had me use it for my email copywriting. Now, we’re using it with all of our coaching clients. We’ve dubbed it the “60-Second Torture Exercise”. And it’s dead simple. Set up a timer for 60 seconds, and allow yourself just that one minute to write a first pass at your email body copy. What this will force you to do is be punchy and concise. You’ll get in. Make your point. And get out. 

You can then use more time to revise your copy and make it better through edits and the like. But that first pass in 60 seconds will set you up for success. It’s a bit like forcing yourself to splatter paint on a blank canvas. You’ll be on your way to a masterpiece in no time.

The second thing you need to realize is that our retinas and brains have become incredibly well-trained to recognize automated copy. Within half a second, we’re able to look at an email and know if it was written for an email blast versus something more personalized. Your job is to beat that system. Even if you’re doing email automation. 

You might ask, “Well, how do I do that?” By writing like you would to a friend. An email that looks like you wrote it to a friend won’t reek of formality and is much less likely to trigger our automation detectors. Now, this might not be an easy habit to build. Most of us have to unlearn all the proper business English we were taught in school. You have to unload excessive formality and inject your personality into your writing. Do all of that, and you’ve got a much better shot at grabbing your prospect’s attention and engaging them.

 

 

 

We tend to think that our email body copy is the most important thing we’ll be writing. 

But you could send a blank email if it’s left unopened by your prospect. 

Your subject line is your pickup line. If you don’t elicit curiosity and have your prospect click on the email, there’s no need to spend time writing the body itself. 

The same goes for the first and last few lines of your email. If you don’t write something attention-grabbing and compelling, your prospect might open the email, start reading it (or skim down to the call to action), and press “Delete” before giving it a second thought.

 

Founders don’t devote enough attention to their subject lines and the beginning (or end) of their outbound messages.

Paying close attention to what you write early and late in your messages will do you good. Put yourself in your prospect’s shoes. 

What would intrigue or titillate them? What would get them to read on? 

Those are the questions you should be asking yourself as you write your subject lines and email body copy. A quick example to illustrate this: when coaching our clients, we tell them to never capitalize any of the words in their subject lines. Something as minute as that changes the way the prospect interacts with the subject line. Instantly, the message feels personal. And your brain can’t reconcile it coming from a marketing automation tool. “It must have been penned by an actual human being, sitting behind their typewriter, thinking of me exclusively.” Well…part of that might be wishful thinking…but a prospect can dream.  

If you take your craftsmanship seriously, you might come up with subject lines that are similar to some of our favorites. “quick question” is a classic, as it tends to feel like something you’d write to a friend or acquaintance. And who doesn’t get curious about a question being directed at you? We are trained from a young age to answer questions that are asked of us. Why would that change in this email medium? 

Another fun one that works well is “how’s Croatia?” This one we’ll tend to use as the subject line for a breakup email. That email asks the prospect if they’re enjoying Croatia from the top deck of their megayacht as they’re sipping on Dom Perignon and being fed caviar. It paints a surreal picture of them without a care in the world because they’ve completely solved all the problems they have ever faced in their professional lives. As they’re most likely not on the Mediterranean on a large boat, they have to ask themselves, “What am I missing? Why don’t I jump on the phone with Matt so he can help me solve some of my issues?” What started it all, however, is the catchy subject line. If you’ve never been to Croatia, or are not there at the moment, you’re going to be asking yourself why you’d receive such an email, and will likely click on it out of curiosity.   

Lastly, any time you can include your prospect’s first name in a subject line, it’s a good thing. We’ve been trained to respond to our name since shortly after birth. We can leverage that instinct by making sure we call upon the prospect in subject lines like “quick question, [FirstName]” or “feedback from you, [FirstName]?”. 

An advanced tip for you: In an outbound LinkedIn message, your recipient will be able to not only see your message’s subject line but also the first 5 to 8 words. The more alluring these are, but more likely you are to engage them in a conversation. Make sure you make those lines snappy and differentiated from anything else they might receive from LinkedIn messages. Here are some examples:

 

Hey Marc, I sent you a couple of emails about sales consulting. Did you see them? 

Or 

Hey Marc, I went to USC, and graduated in 2005. Would be great to connect with an alum. BTW also saw you know Peter Smith – he’s a good friend!

In each instance, the first bit of the message has a high probability of tickling your prospect’s brain. The first one mentions emails that have been sent. It’s likely to elicit a little FOMO. Who wants to miss an important email? The second LinkedIn message makes sure to point out two things the rep and the prospect have in common – going to USC, and having Peter Smith as a connection. It’s hard to ignore someone who went to your alma mater. And if Peter Smith is also a close friend, it’s almost impossible to imagine the prospect wouldn’t respond to this message if they see it.

 

 

 

Founders are anxious to sell. And rightfully so.

Without sales, all you have is a product. You don’t get to have a company. Nor do you have a business.

But in that haste, sometimes, founders will try to sell too fast in their outbound communication. Their call to action in an outbound email might be to try to get you to sign up for a free trial. Mind you, they haven’t given you a demo. And their product costs several thousands of dollars per month. 

The result?

Prospects feel rushed. They’re being steamrolled by the incoming founder, without allowing them to fully comprehend the value of the product they’re being pitched.

 

 

Founders try to sell their product or service in one email.

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

In the very same way, in outbound email campaigns for nearly all B2B products: you shouldn’t try to get the transaction with one cold email. It’s unrealistic. Even asking the prospect to sign up for a free trial is asking too much, in most cases. Your goal should be to generate an introductory conversation. To book an intro call.

That’s it.

If you start thinking about selling your product outright, your copy will be too long. Your message will be diffuse. You’ll run the risk of losing your reader in long feature lists and other benefits. Your message will most likely come off as a hard sale. You’ll end up striking out because you looked to crush the ball over the right field fence when all you needed to do was get on base.

Here’s an email that tries to do too much:

 

 

[FirstName]:

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

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

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

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

Let us know if you have any questions.

Cheers,

[SalesRepName]

If I were approached with this type of email, I’d instantly be turned off. The sales rep has no intention of getting me on the phone, nor is he willing to answer any of my questions. Never mind a demo of the software. 

The email does a good job of establishing credibility and social proof, but it falls short as it attempts to convert me right away without offering to take care of me. It could have offered to handhold me through an established process. And yet, I’m getting pushed through to a free trial. Even folks who hate chatting with sales reps will feel awkward by the approach above. A tiny group of folks might go for a free trial, but the vast majority will not react well. They more than likely won’t click on the link, nor will they respond to the email.

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

 

[FirstName]:

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

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

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

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

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

Thanks!

Cheers,

[SalesRepName]

If you think like this — getting that critical first down instead of throwing up a Hail Mary — your copy becomes short, crisp, and to the point. And your prospects won’t feel like you’re disrespecting them. The email’s sole purpose will be to pique their interest enough to have them agree to a quick first meeting.

 

 

 

 

Founders are a rare breed. 

They’ve set out to put their dents in the universe.

And they are willing to take large risks to get there. The odds of making it are long, and the hours brutal. 

It’s also very lonely. 

Not everyone is willing to sacrifice it all to make the world better. Because founders are no ordinary people, they usually gravitate to one another and bond when they first meet. 

Game recognizes game. Cut from the same cloth, they sniff each other out as members of this rarified air. 

And yet, founders forgo leaning on this commonality.

 

Founders forget to leverage one of their main strengths: founder-to-founder kinship.

One of the ways founders can leverage this kinship with fellow founders is by introducing themselves properly and asking other founders for feedback. The founder on the receiving end usually sees themselves in the outbounding founder and feels obliged to respond. 

After all, they’ve been in those shoes and have trekked that solitary, treacherous path. Yet very few founders think to leverage this advantage they have over others. 

There’s even a bonus corollary to this maxim. Prospects – even non-founders – would rather talk and interact with founders than coin-operated salespeople. This translates to higher response rates and more introductory calls booked. 

It makes complete sense. If you’re a prospect who suffers from a pain point that was mentioned in an outbound email, you’re more enthused to talk to the person who has studied the problem intensely and crafted a solution over the past two-plus years, than a salesperson whose sole goal is fattening their next commission check. 

Who could blame you? Empathy for your problem is going to overflow from the founder. They’ve gotten so close to the issue you’re facing they can taste it. Even if they didn’t directly suffer from it. Knowing this founder has invested great chunks of their existence making something that will enhance your life has you leaning in. “You understand me!”, is the overwhelming feeling you get when thinking about the founder’s dedication to your cause.  

This is such a powerful force in go-to-market, that we often recommend that hired sales reps impersonate their bosses – the founders – in their outbound messages. It’s a shrewd tactic known and widely used in sales circles. The delta in difficulty between breaking into accounts as a founder and doing the same as a salesperson is a major reason why going from founder-led sales to salesperson-led sales feels like an arduous transition for most startups. But more on that in future writings.

 

It might seem like a tiny faux pas. Benedict Evans certainly doesn’t think so, in the tweet above.

Why would anyone care if I sent them a Calendly link in an outbound email?

First of all, I don’t make the rules. Human beings have gotten offended by much smaller things. You can hold your fork a certain way in some social settings and some folks will think you’re a peasant. The fact of the matter is sending over a Calendly link to schedule an initial call when doing outbound can feel like a power move to some people (usually the old guard, I’ve found).

​

Founders use calendaring software exclusively to schedule the initial call.

When you’re getting an inbound request, it’s very different. The prospect is coming to you, and expressing interest in your product or service. Asking them to schedule through Calendly is much less abrasive. When you’re reaching out to folks unannounced, and you’re putting the burden of scheduling the call on them, you’re bound to get some negative reactions.

Some people – usually the younger, more tech-savvy crowd, I’ve noticed –  won’t mind and even welcome the opportunity to use a Calendly link to reduce the email back and forth. In my experience, technical and product folks fit in that group. But you’re going to get folks that find it off-putting that you reached out cold, and then had the audacity to seek their help in scheduling.

The bottom line is, as a salesperson, it’s your responsibility to cater to your prospect/customer; in this case, shouldering the scheduling work.

My simple suggestion here? Ask the prospect what times work best for them and offer a calendaring software link as an alternative they can use as well. That way, you’ve got all of your bases covered.