B2B Wins #44: The Technical Founder's Guide to Not Screwing Up Sales
And you thought building product was hard
I talk with a lot of founders. Those discussions are equal parts business development and networking. I love to hear what people are working on. It helps me think about my own founder journey. Sometimes I can help them because I’ve done what they have done. Nothing teaches like experience.
I also love the early part of the game. A founder believes they’ve solved an important problem and now has to illustrate to the world that this thing exists. They have to convince buyers that it creates value by solving an important problem. It’s in that convincing that many founders flounder.
It is easy to tell when a founder is going to struggle with sales. Ask them to pitch you like a customer. Give them ten minutes. Just listen.
Many times, they describe what they do and I still have no idea what they’re up to. It’s rarely because the domain is so foreign to me that I don’t grok the concept. It’s usually because they’re either wrapped up in buzzwords that mean nothing or deep in the technology. Or both.
The final tell is that they don’t ask a bunch of questions.
This is a common pattern. They've built something incredible, but they're selling it all wrong. They're selling what they built, not what it does for the customer.
The Technical Founder's Advantage
Before we dive into what technical founders get wrong, let's talk about their unique advantages in sales. Yes, technical founders have some natural sales advantages:
Deep Product Knowledge: You built it. You know every corner case, every feature, every limitation. When a technical buyer asks a hard question, you can answer it with authority. As the non-technical founder, I always had to roll out the technical people when things got deep.
Credibility: Technical buyers trust other technical people. When you can speak their language, you instantly build credibility that traditional salespeople spend years trying to develop.
Real-time Problem Solving: In sales conversations, you can identify novel solutions to customer problems on the spot. You don't need to "check with engineering." You also have to be careful here. You’re selling a product, not services. So, don’t let one customer take you off your product roadmap. Do enough to get the money but not so much that you get distracted.
Direct Feedback Loop: You hear customer needs directly and can translate them into product improvements immediately. No game of telephone between sales and engineering. This is one of the biggest advantages. In the early stage, the product you’re building is going to evolve in both large and small ways. Getting this direct feedback from potential customers shortens those cycle times.
The problem is that most technical founders never leverage these advantages because they're too busy making classic mistakes.
The Classic Mistakes
Let's talk about where technical founders typically go wrong in sales conversations:
Forgetting you have ears
You’re a proud parent of a awesome product. Of course you want to talk about it. But sales is more about listening than about talking. Especially in early calls, you’re just trying to figure out who you’re talking to, what business are they in, why they called you (or took your outbound call), what they’ve done so far to solve the problem, and why that didn’t work. Ask open ended questions. Listen a lot.
Leading with Technology
The most common mistake is starting with HOW it works instead of WHY it matters. Yes, your elegant architecture is amazing. No, your customer doesn't care (yet). They care about their problems.
At my last startup, we had a patented technology that analyzed behavior to improve knowledge management. It was highly differentiated from our competitors. Customers didn’t care about how it worked. They cared about how it solved the problem of hidden data within the enterprise.
Feature Dumping
Technical founders love to list every feature they've built. It's natural - you're proud of your work. But rattling off features without context is like reciting ingredients without describing the meal.
Don't tell me it has "automated workflow capabilities with conditional branching." Tell me it "ensures nothing falls through the cracks in your approval process."
That sort of simple language resonates with humans. It connects the technology with the pain that they have in their professional lives. Simplify how you talk about your solution. Get rid of all the buzzwords.
Solving Problems That Don't Exist
Technical founders often build solutions for problems they find intellectually interesting rather than problems customers will pay to solve. Just because you can build it doesn't mean someone will buy it.
This mistake should be rooted out before you get to sales. You should be talking to the market about the pain and revising your solution to make sure that by the time you get to selling it, you’re at least over the right target zone.
I included this here because I want you to be open to the idea that maybe you’ve gotten is slightly wrong. Maybe you’re addressing a symptom but not the problem.
For example, you may be helping companies normalize disparate data sets, but the real problem is how they capture that data in the first place. Solve the real problem. (see Direct Feedback Loop above)
Ignoring the Business Buyer
B2B buying is a team sport. The technical buyer is rarely the economic buyer. Technical founders often get caught up in deep technical discussions with the engineering team while ignoring the business stakeholders who actually have budget authority.
You need to be able to speak both languages: bits and bytes with the technical team, ROI and business outcomes with the economic buyer.
You also need to consider the all the other parties that could be involved in approving, or at least nurturing a deal. These include finance and procurement. There may be others. Ask about this during the early part of your sales process.
The Fix: A Technical Founder's Sales Framework
If you’re new to this, here's a framework that will help get you started. This will help you leverage your advantages while avoiding the common pitfalls:
Ask questions. Shut up.
Before you mention a single feature, get the customer talking about their pain. How much time are they wasting? What opportunities are they missing? What risks are they facing?
A founder I work with starts every conversation with: "Walk me through your current process." Then they shut up and listen. The goal is to get the customer to sell themselves on needing a solution before you start talking.
They may already be there, but let them go through the process. Let them demonstrate, to you and to themselves, they’re ready. There’s nothing worse than a customer who isn’t ready to solve their own pain. They’ll never buy. Discover this early. Don’t waste your time with them.
Everyone who has done enterprise sales has been on that call when they realize that this prospect lives in a world of pain and doesn’t mind it. Time to move on.
Paint the Future State
Once you understand their pain, paint a picture of what their world looks like after implementing your solution. Not the technical implementation - the business outcome.
"Imagine if your deployment process took 10 minutes instead of two days. Your developers could ship features daily instead of monthly. Your customers would see improvements immediately instead of waiting for the next release window."
More listening.
Let them give you feedback on that future state. This is going to lead you to the true pain. Maybe it’s not “the deployment process” that’s causing them pain, it’s actually their QA processes.
Validate the Vision
This is where your technical credibility becomes a superpower. After painting the future state, demonstrate that you can actually deliver it. Show them how you've solved the hard technical problems that make that future possible. Validation is what you’re after. If they don’t see it, ask why and listen.
The sales process is iterative. It is often two steps forward and one back. If this solution doesn’t solve the problem, go back and look at the future state vision. Is there something that you or they missed while painting that future state?
Be Patient
B2B sales, especially for large ticket items—those that are six figures and higher—take a long time. It’s a big commitment for the person, the department, and the company. You are going to have to talk to folks from across the organization to convince them that you’re the right solution for their pain. This is part of the journey you’ve signed up for, there’s no easy way around it.
You can help yourself by understanding their buying process right at the beginning of the relationship. If you have this shared understanding, you can work with your prospect to assess how far along you are on the journey and what needs to be done to get to the goal line.
That said, that process is rarely linear. Buckle up.
Speak Their Language
During the sales process you will meet lots of folks. New people will enter the process all the time. Do your homework on them before the meeting. Also, start every meeting but asking them about themselves. Who are they? What do they do? What is their role in the buying process? What do they think success looks like? Lots of listening.
What you’re trying to suss out is what language do they speak.
Learn to tell your story at three levels:
Technical buyer: Architecture, security, scalability
Business buyer: ROI, efficiency, competitive advantage
End user: Ease of use, time savings, reduced friction
You need to be fluent in all three languages and know when to use each one.
The Counter-Intuitive Truth
Here's the thing that most technical founders find hard to accept: In early-stage B2B sales, your technical expertise is both your greatest strength and your greatest weakness.
It's a strength because it gives you credibility and allows you to solve problems in real-time. It's a weakness because it tempts you to focus on the solution instead of the problem.
The key is to keep your technical expertise in your back pocket. Lead with customer problems and business outcomes. Then, when someone questions if you can actually deliver those outcomes, unleash your technical expertise to prove that you can.
Remember, customers don't buy technology. They buy solutions to problems. Your job isn't to educate them on your amazing technology. Your job is to convince them that you can solve their problem.
Don't hide your technical expertise - just learn to deploy it at the right moment in the right way.