One of the biggest mistakes I see founders make is not doing sales themselves.
I get it, sales can be uncomfortable if you don’t have a background in it. But as a founder most of your job is sales:
Selling candidates on why they should join
Selling investors on the vision and potential
Selling customers on how your startup will improve their lives
You simply have to get good at it. Introducing middlemen between you and your customers leads to slower learning and faster failure.
Yes, there will come a time when you simply don’t have bandwidth to do all sales yourself, but you should fight against that for as long as possible. I’m currently doing all demos for Megaphone, for example.
And if you spend a lot of time on X like I do then you’ve probably seen some hot takes from Jen Abel (co-founder of JJELLYFISH) about how startups do sales, including that startup sales talent doesn’t exist.
She’s one of my favorite, underrated follows on X and this week I interviewed her about some of her spiciest and most on point posts from the last few years.
Thanks for being a member! Since this is one of our ✨ members-only ✨ deep dives, you can read the full post below.
Founders Need to Lead Sales
Q: Why Does Doing Sales Make Your Startup Move Faster?
The market is most excited to learn from a founder. In the absence of brand equity, founders alone have the social credibility to get meetings that other people would get turned down for. Potential customers want to talk to founders because they know founders can make something they may want. This short feedback loop increases velocity through the entire company and also avoids a game of telephone that can lead to bad decisions. |
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Q: Why Do Customers Buy Half-Built Products?
When the pain is severe and unmet by existing solutions, people are willing to take a risk on a new approach. If you’re building something the market really wants then they’ll forgive imperfection. The greater the want, the more imperfection they’ll forgive. If your industry is regulated, abide by those, but otherwise apply this philosophy. |
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As a note from me, this is exactly how I’ve been building Megaphone. At this point I’m trying to ship features fast enough to keep up with demand, but every step of the way our users have forgiven imperfection.
We’ve had a janky, Typeform-based onboarding flow for months. Not ideal, but forgivable in the short-term if the product delivers results.
The key is finding the things that really move the needle and trusting your customers to understand the imperfect parts can and will be smoothed out over time.
Q: Why Focus on Sales Instead of Marketing?
Y Combinator’s co-founder Jessica Livingston says that if you can’t inspire the market in a one-on-one setting, how can you expect to inspire them in a one-to-many setting? In marketing, the more specific you are the more trust you’ll build. And you’ll only get to that level of specificity in your message if you go out and learn in one-on-one settings. This is highly related to your startup’s economics, the more specific you’re able to get, the lower CAC you can achieve. |
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I highly recommend reading Jessica’s full blog post (it’s literally one-paragraph).
Q: Should Sales Ever Lead a Startup’s Product Roadmap?
The market has no idea how to solve the problem your product is trying to solve. Having sales lead product means their interpretation of what the market admittedly doesn’t know guides your resource allocation. If the market responds poorly you’re either targeting the wrong market or overbuilt something that hasn’t been validated. The answer is a shorter feedback loop, not a sales-driven roadmap. |
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Q: Why Does 0 to 1 Sales Talent Not Exist?
The vision you start with isn’t what will take you to PMF, it’s nearly impossible to be entirely correct that early on. And when your solution isn’t validated yet, there’s nothing to sell. Sales requires structure, a process, and the ability to define a good lead vs. a bad lead. Until that’s built, it has to be founder-led sales. |
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Q: When Should Founders Hire a Salesperson?
Most founders feel they’ll be the bottleneck in the sales process. However this is not reality unless you’re over $1 million in revenue. In the 0 to 1 stage the founder will excite the market and be able to make the quickest decisions. Delegating decreases your odds of success. The right time to hire someone for sales is if your calendar is full of sales calls and you’re losing out on meetings as a result. You’re not a bottleneck if you have open time on your calendar. |
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Honestly, what’s higher leverage that growing your startup? Spend your time on high leverage tasks.
Q: Why Does PMF Happen In Adjacent Markets?
Founders tend to start with an obvious insight. That’s ok. It’s a good starting point. The problem is your early adopters will only become true fans once you figure something out that the rest of the market hasn’t yet. And only a founder can see something forming when they’re not actively searching for it, everyone else is just doing “their job.” |
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Q: In What Ways Does Competition Matter For Sales?
Think about it from the perspective of alternatives. 9 out of 10 of your customers are just using the status quo from their own companies. It doesn’t matter what marketing your competitors are doing, but speak to your competitors’ customers. This is the best way to learn. Identify the secondary job-to-be-done that your competitor isn’t doing, then build that and peel off initial customers from them who are underserved. |
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Q: Why Should Startups Not Sell to Enterprise?
The length of a sales cycle that a pre-seed to Series A can afford to enter into is at odds with what’s required for true enterprise deals. Enterprise deals take 12-24 months. That’s more runway that many startups have. Your time can be better spent growing the business. Candidly you may not even be around by the time the deal would close. You also have to be building an enterprise product. Sales is hard enough, you don’t want to have convince enterprise customers during the sales cycle that what you’re building will maybe eventually solve their problem. Enterprise deals also require two levels of PMF:
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Marc Andreessen calls this his moby dick theory. There’s all these internal things that can happen, internal politics, your champion left the company, etc to kill the deal.
Founders should focus on what they can control.
Q: What are the Two Jobs in Startup Sales?
If you don’t understand the customers’ problems better than them, how will you convince them to buy? You’re working to expand their world of possibilities, not anchoring on selling a “tool,” sell the problem. More importantly, speak in their language, how are they describing the problem in their 1:1s internally? They need to go back and speak about that pain to their teammates. You need to know what’s going on under the water, so to speak. |
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Q: Why Do All Startup Roads Lead to B2B Sales?
If you want to be a big company, you need to be able to sell into big companies. Even companies that start B2C like Facebook/Meta, or are known primarily for their B2C product like OpenAI with ChatGPT, invest heavy resources into their B2B offerings. Go where the money is. |
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Q: What are Your Top GTM Predictions for 2024? Any Other Thoughts?
In 2023 there was a fast march upmarket, in 2024 there will be a quick retreat downmarket, especially for companies who’ve leaned into product-led growth, where startups will spend time securing revenue and proving out their experiments.
This will be caused by the realization that experimental solutions take too long to prove out when selling into the enterprise tier for startups that don’t have much runway.
Also, the startups that win will find ways to run experiments in the absolute easiest way possible because round sizes remain down and funding is hard to come by.
Finding initial PMF only affords you the ability to run the next experiment with your next round of funding. You can negate the impact of finding PMF if you move upmarket too quickly. Take the next step on the ladder, from startups to mid-market, don’t skip rungs.
This is the inverse of what you often see in consumer, like with Tesla’s initial upmarket roadster eventually leading to a mass-market consumer sedan.
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