“Paul, cold email never works on me. I don’t think we should try it here.”

“I don’t feel comfortable reaching out to folks in this manner. It just doesn’t feel natural to me.”

“We’re going to go back to building product. Once it’s perfect, it will just sell itself.”

Just some of the concerning statements I’ll hear from founders in session, as we think through their go-to-market strategy.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your seventh and final installment.

Last week was about designing and ranking experiments. Their importance in answering the questions you have for the market. Questions elicit experiments. And the experiments garner answers. In go-to-market, the earlier we get to a successful experiment, the better off we are. Because, we can scale it, and start generating sales conversations in a repeatable way. Thus our reason for ranking the designed experiments based on their likelihood of success.

This week, let’s get into the disposition you should have as a founder when it comes to your go-to-market. Mentality that – as you’ll see – is far from the pronouncements made above.

The most successful founders are those that are looking to learn from the market as much and as quickly as possible. Those who remain humble and agnostic as to what might work. They may have strong opinions about what experiments might be successful but they’re more than happy to put them to the test, and even relish in being proven wrong. They lean into the market relentlessly.

Ever see how a surfer relates to the ocean? The surfer reveres the water he floats on. And rightfully so. The ocean is a much greater force than the human riding its waves. I invite my clients to see the market in very much the same way. Even if we end up growing our startup to become a Fortune 100 company, the market will still be a much more powerful force than we will ever be. We therefore need to treat it with the utmost respect. Bow to the market, and learn how to listen to it. After all, it holds the truth. Our job? To interact with it, listen to it carefully, and iterate on our go-to-market approach based on what it’s telling us. Perhaps the most important skill I teach my clients over time is this ability to read the data and feedback coming from the market. It all starts with a strong dose of humility, and a reverence for the market.

You might now ask me, “Well, Paul, that’s all well and good. I already think the world of the market, and what it has to teach me. But what does listening to the market look like in practical terms?”

Great question. Qualitatively, here’s an example to illustrate what I mean. You get a “please remove me from your list” reply from a prospect that you had sent an automated email to. What does one do with that? Well, you need to go find out why you got that response, by humbly asking your prospect for feedback. Once in a while, you’ll land on a golden nugget. One that ends up completely transforming the way you go-to-market.

“The pain point you mentioned in your email isn’t something we deal with a lot. It didn’t feel worthwhile to continue the conversation”, your prospect replies.

Yes, this is a small sample size. N of 1. But one reply might have you realize that you ought to be leaning on another pain point as your entrée into a sales conversation. Next thing you know, you’re deploying a different pain point in your email campaigns and they take off.

How does listening to the market look like quantitatively?

Glad you asked. A 4-step 100-lead automated email campaign gets fully deployed and the data is in: a 60% open rate and a reply rate of 3% with no interested replies. Now, what does that all mean? Our emails are getting delivered in inboxes and our subject lines are strong enough that folks are opening them. The missing ingredient is email body copy that’s more engaging. Our emails are presumably getting read at a good enough clip. What’s missing is copy that gets people to reply. And respond to us with interest. We ought to take a closer look at the offer/CTA we’ve put forth. Can we make it more value-laden and immediately attractive to our prospects? Can we dangle value so irresistible prospects have no choice but to book a call with us?

This is a glimpse as to what you need to get to when it comes to listening to the market. I’ll allow myself a detour to not only show you how sophisticated you need to become in that realm, but also to perhaps challenge the way you’ve been thinking about go-to-market overall.

A few years back, a European software vendor approached us with a problem. Despite having 13 or 14 big brands as customers – companies anybody that has been involved in business for even a couple of years would recognize – they were having a hard time generating consistent pipeline. And they wanted to do so through an automated email initiative. I was amazed they were struggling with their top-of-funnel with such big name customers as social proof. Their ACVs were $60K. I got this startup’s CEO to agree to giving our engagement at least 4 months. This – all while knowing – that it can sometimes take upwards of 12 months to find message-market fit. We set forth on building out this initiative. And launched it.

See the report below from this outbound buildout. Do know that we never share client data unless it’s been completely scrubbed and anonymized. Which this has.

Which this has.

 A few things to note about this anonymized report. First, each row is a different campaign that was launched. Second, the taxonomy of each campaign name works as follows. It starts with target vertical. Then goes to launch date. Only to finish with copy variation. Also, every teal-highlighted row is one that has reached the 1% interested rate plateau or above.

Now, check out what happens with this automated email initiative. After launch, we don’t get our first interested reply till our fourth campaign. Then we go ambling into the desert without much to drink for a while. We only get a gulp of water – our 2nd interested reply in our 19th campaign. Then nothing till our 31st campaign; where we got our 3rd interested reply. And then nothing till our 40th campaign – where we get our 4th interested reply. 40 campaigns. Only 4 interested replies! Tough sledding, right?

Look at what happens next, however. Teal starts appearing quite a bit more. So much so that about two, two and half months in, in the span of 5 campaigns – three of which are at 400 leads, we generated 18 interested replies. And four and a half, close to five months later, we generated 36 interested replies in the span of 6 campaigns. All at 400 leads. At this point, we’re getting to message-market fit. We’re generating hundreds of thousands of dollars worth of pipeline on a weekly basis. This report gets cut off below for our purposes. But it kept going. We worked with this company for over 18 months. Close to 2 years. They ended up integrating our process, bringing it in-house. Needless to say, they were thrilled with us.

I’m showing you this report for two reasons. The first? If we were to inject this startup’s CEO with truth serum today and ask him, “Were you thinking about pulling the plug on this initiative two, two and half months in?” I’d bet you he’d say, “Yes!” I could hear his impatience and anxiety in our weekly calls with him early on in the outbound buildout. The other reason? When I meet with founders and startup operators, I’ll sometimes ask them if they’ve tried automated email, among other go-to-market channels. And they’ll respond, “Yes, but it didn’t work.” I’ll then ask, “How many campaigns did you launch?” “Eight campaigns and we only got a couple replies.” My usual response? “I don’t think you quite understand what it takes to find message-market fit.” The report above shows an arduous journey to message-market fit. A lot of times, we don’t feel like we’re getting enough dopamine to keep going. Hopefully this document shows folks that it’s possible to get there if you have enough persistence, know how to write good outbound copy, listen to the market well, and possess advanced data analysis skills. Now, we’ve seen and worked with startups that get a lot more teal earlier in the process. But it’s important to note that this report exemplifies what it can take to get to message-market fit. And if folks give up too early on this — or other — channels, they run the risk of never giving their product a chance to see the light of day.

Having seen all of this, how has your understanding of go-to-market changed? And how sophisticated do you think you are in this realm?

I ask because a lack of sophistication in go-to-market could be the difference between finding a repeatable way to get in front of customers, and not having your product ever get a chance to move off your shelves. Which group do you want to be in?

If it’s the latter, I’d encourage you to find the help you need to get this know-how and sophistication as quickly as possible. As you can probably now tell, prospecting takes a lot more sophistication than you had imagined.

Then why go at it alone?

Getting a good coach that knows the ropes can help you accelerate your learning and make sure you adopt the right disposition to tackle your market. I’m here as always if you want to chat. For anybody that writes in, in response to this episode, I’ll happily offer a free hour-long coaching session. You bring your top thorny sales and GTM issues, and my job is to help you through at least one of them. As always, take these learnings, use them out in the market and report back. I’m eager to see what sticks with folks and what ends up working for them. Chat with you soon, hopefully.

This was the final episode of the Founder-Led Prospecting series. Hope it was useful. If you’re landing on this installment first and would like to start where it all began, here’s our first episode. Remember: prospecting is far from glamorous but oh so essential to your sales. And thus your startup. Give it proper attention, and you’ve got a shot at surviving. Ignore it or bury your head in the sand, and you’re more than likely headed to the startup cemetery.