"I want your playbook."

"Paul, we want your playbook."

I get this every so often from founders.

And it's concerning. Because it shows a lack of understanding about what startup sales and GTM are really about. There's no universal playbook for all startups to follow. If there were, there'd be no need to even build out a go-to-market motion. We'd all download the same playbook from the internet. Apply it. And start raking in cash. Yet, that's just not how things work. Instead, building go-to-market factors in many intricate dimensions that are unique to your startup.

For one, your product. Hopefully, it's differentiated, if you want to be able to sell it against other tools. We need to consider many factors. How do we make it stand out in the way we convey its value? Once we start chatting with folks, how do we position our offering so as to minimize the objections we get from prospects? If I were selling an accounting tool, for example, I'd want to make sure I have a clear message as to how it beats out Quickbooks. The classic SaaS way of doing things would be to go feature-by-feature. And that can be effective for some products. I like to think of your overall competitive advantage. Something we can lean on to compel people to buy us over other alternatives. An example might be, “Our interface is built to make your accounting team as efficient as possible. We realize that their most important resource is their time. The average accountant who uses us gets back 15 hours of week, they can then devote to higher value tasks.” Now you're cooking.

Let's consider your team. The people doing sales and GTM as your startup have a set of capabilities. Strengths and weaknesses. I want to answer this question early in my work with clients: What are they good at? And not great at? If the founder running GTM is flustered on the phone, but a brilliant copywriter, that will play a role in orienting the experiments we're going to run. There's a great chance that experiments that feature copywriting, like outbound email, will outweigh those that involve the phone, like cold calling. Now, that doesn't mean that cold calling will never play a part in the startup in question's go-to-market strategy. But, in finding our way to market, we're going to work with the assets and limitations possessed by our startup's team members. Not factoring in those constraints would be a crime.

Our market is next. A determining factor in elaborating a go-to-market strategy. What personas should you be targeting? How should you make your way into the company you're selling to? What entry points should be considered? Believe it or not, your best entry point can be counterintuitive. At Whitetruffle, for example, where I ran sales before starting this coaching practice, we found that our ideal entry point was not internal recruiting – which most often was our end user – but the technical leader (VPE/CTO). After some extensive testing, we realized that going through the VP Engineering or CTO shortened our sales cycles and increased our lead velocity. You might be thinking, ‘How did they figure this out? Why did the indirect route end up being the most successful one?’ Glad you asked. The technical leader at any startup can be considered the most powerful department head. Right along with the VP of Sales. What that department head says generally goes. And internal recruiting, we found, generally would view our VP Engineering or CTO as an internal client. If the technical leader had a quick conversation with me and was convinced Whitetruffle could help, any recommendation they'd make would carry a huge amount of weight. Internal recruiters would move mountains to have meetings with us and leverage our product. We also had the advantage that our product would seduce technical leaders intellectually. We were solving a human problem – finding relevant tech candidates – with a matching algorithm that looked at 50+ core signals. That tended to pique an engineering mind's curiosity. Lastly, and most importantly, even though recruiters would use us, they weren't the ones feeling the pain we solved most intensely. If a VPE or CTO couldn't deliver on product on time, it was their derrière that was on the line. And not delivering was usually due to too few technical resources, which we helped solve by providing candidates at the top of their recruiting funnel.

Next up? Your channels. The question here is: where do your customers hang out? Are they scouring LinkedIn all day, interacting with folks? Do they spend their time in their inbox, feverishly answering emails all day? Can you find them in Slack communities? Do potential customers search for solutions on Google? Are they likely to pick up the phone if we're to call them cold? These are all questions worth asking and answering, as we're building out your GTM. We're going to want to figure out how to reach your customers, and that starts where they spend most of their time. Over the years, I've come to discover some insights that can help advance the channels discussion. Here's one: IC engineers are rarely in their email inboxes. As someone who grew up in the professional world being rewarded for my responsiveness, I used to think, ‘How could they not respond to emails for days?’ It just didn't make sense. Until I realized that engineers were recognized for something completely different than salespeople (which at times has the two groups not seeing eye-to-eye). An engineer is here to build product, to deliver code at all costs. Meaning, they'll gladly isolate themselves from other distractions – like answering emails – for hours-long stretches of deep work. What's been referred to by some as the Maker's Schedule.

Let's remember that infrastructure plays a large role in how we'll conduct our foray into the market. What tools should we use in order to best execute on our go-to-market goals? If my target customers were internal recruiters at early-stage tech startups, I'd probably want a tool that enables me to automate both LinkedIn and email. Internal recruiters are typically both in their email inboxes and searching LinkedIn for potential candidates to fill roles at their companies. Amplemarket – an avant-garde marketing automation tool – would be at the top of the list for tools to help me accomplish these things. They go as far as to identify hand-raisers within your leads and enable you to target them with timely messages. At our coaching practice, for example, we've designed and run campaigns targeting founders making their first sales hires. Our pitch has essentially been, “I just noticed you're hiring for new reps. Let me help you through the treacherous transition from founder-led to salesperson-led sales. I've facilitated this passage many times, and I'd like to help prevent this from being a painful and costly move.”

We're saving perhaps the best for last. Messaging shouldn't be ignored. What content should we put in front of our target customer, and at what cadence, to get them to respond with interest? What would get them to want to have a conversation with us? A slew of different facets need to be weighed and reviewed here. One of them might be the ingredients you have to produce great outbound copy. We call these building blocks. Just like making a great meal is nearly impossible without great ingredients, crafting great copy without great building blocks is an arduous undertaking. For every persona you target, you're going to want to have relevant outbound copy building blocks: pain points, value props, quantifiables, social proof, and CTAs/offers. Without many options to choose from in each category – we nudge our clients to get to ten in each – it's tough to come up with enough copy variations to reach message-market fit in automated email outbound. Once you have these elements in play, you've got to possess the necessary skill to transform them into crisp copy likely to elicit interest from prospects. Yet another challenge for us to discuss and get over together.

If there's no playbook, then where can a sales/GTM coach like me help? I've seen the movie hundreds of times, so I can help you navigate all of these thorny variables. I can help you devise experiments that have a greater likelihood of success. In large part because they incorporate the latest best practices in go-to-market. The cutting-edge techniques give you the best chance to succeed. Example: email deliverability is a coevolutionary arms race. Companies like Google and Microsoft fight like hell to prevent spam. They employ armies of developers and data scientists to build smarter ways to recognize spam and place that email squarely in the “Junk” folder. As a startup that plans to send automated email outbound, you've got to be armed with the latest and greatest in email deliverability protocols that will help you mitigate the negative impact of spam filters. Among other things, that means using the right email inbox warmup tools, avoiding words that will trip up spam filters, and using sophisticated features that rotate portions of your copy in and out to mix things up.

I can also help guide your thinking around go-to-market. I'll provide you with insights that will save you weeks and months of trial and error. "If you're targeting recruiters and HR people, LinkedIn is a channel we should strongly consider. Because those folks hang out there all day long. I can't tell you how many clients have been generating bites there. It's almost like these folks live on the platform 24/7.” Or, you might hear this in one of our coaching sessions, “Your email subject line is your pickup line. You can have the best email body, but if you don't nail the subject line, all you have is air. Most startup operators don't spend enough time on them. The subject lines we're going to want to come up with must be short, crisp, and curiosity-inducing. What can we come up with that will have folks want to click on them? Here are some examples that have worked well for us and our client in the past…” Or I might advance this as we work through who to target as a way into a company, “I can tell you that salespeople are actually great entry points into the fortress because they respect the hustle. They understand the power of connecting people and getting at-bats. The good ones have been groomed their entire careers to be responsive and service-oriented. There's a greater chance they'll be willing to intro you to the decision maker within Acme Corp.”

You're also going to want to make sure you acquire the necessary skill of reading the feedback coming back from the market, as we interact with it. You're going to want to be able to read feedback coming back from it, qualitatively and quantitatively. And act on what it's telling you. The fact of the matter is: the market is a much greater force than we'll ever be. And just like the surfer reveres the ocean, we need to bow to the market and learn how to listen to it. If I were to ask you, "What does it mean to have a 4-step automated email campaign that has garnered a 60% open rate and a 3% reply rate? What do you do with that?” Or “What does a 15% connect acceptance rate mean on your LinkedIn outbound campaigns?” I'd want you to know exactly what to do with them. What to keep and what to scrap. What to double down on. That's a skill I'd hope to develop in you in the first 6 months of our work together. It's like teaching you how to fish. Because once you've learned it, you don't go hungry for very long. And as you're in the process of sharpening that skill, I can act as your pair of eyes and ears. Making sure you don't miss out on any market insights.

At the end of the day, you'll have to set up a sales laboratory. One where you can devise experiments. Rank them based on their likelihood of success. And then run them. Only to read the results and figure out what to do next. Without it, you won't be able to learn fast enough about the market, and conform to it over time. Startups are experiment machines that enable us to learn about the world. The faster the cycles, the better. Because startups are also ticking time bombs. The length of the fuse is your runway. You need to figure out a way to get to market effectively before time runs out. What's one of the best ways to accomplish that? Bring on someone who has done it several times over. Happy to jump on a call anytime to see how I might be able to help. Just reach out. Let's figure this out together.