How I Learned to Sell a Dozen Large Deals as a Technical Outsider

By Sébastien Boyer, Founder of FarmWise

Here are some learnings from selling AI-powered robots to old-school farming execs and why I think running sales yourself as a technical founder, however unnatural it may feel, is the best path.

When I started FarmWise, I was a math and CS grad student from France with no ties to American agriculture. I had never worked a day on a farm. Our target customers were large farm owners in California who hadn’t the slimmest idea about what AI was (that was during AI pre-history in 2017).

The ag market is notoriously hard to crack. Relationship-driven. Risk-averse. Local. The most common advice I got then was to hire “sales guys” who looked the part: mid-50s, boots, a background in equipment sales. I saw a lot of small startups in ag do this. I couldn’t afford that. I didn’t know anyone who could fit that description anyway. So I decided to give it a shot myself. I struggled a lot with being taken seriously, getting in front of the right decision makers and closing even our first free - short term - non binding - pilot letter of intent. But through these struggles, I learned a few things about sales and eventually turned the dynamic around in our favor.

After eighteen months, we had 12 large ag customers across California and Arizona. That traction helped us raise our Series A. Looking back, I think running sales myself as a technical founder/CEO was by far the best path for us back then and I think very often the best path for technical founders. Here are a few things that I learned, that I think helped us a lot, and that I hope can help technical founders approach sales with more serenity.

TL;DR – What Worked

Replaced early sales hires with an advisor playbook, using equity-aligned industry insiders to get warm access where cold outreach failed
Treated sales meetings as structured experiments — testing a core hypothesis, logging results, and iterating messaging like product
Stopped performing credibility, instead earned it through vulnerability and obsessive, unscalable, customer research

Advisor Playbook: Credibility You Can’t Fake

Companies live and die by how deeply they understand their customers—and my first challenge was getting those conversations in the first place. I could brute-force outreach, but not trust. I was a 20-something outsider selling robotics into a traditional industry. Hustle alone wasn’t enough. What changed everything was bringing on the right advisors.

But not just anyone who called themselves an advisor. The first people I met in ag weren’t the most relevant. The ones who proactively pitched themselves as advisors were usually quite unhelpful.

What worked was asking people in the industry, “Who do you trust?” and then trying to build relationships with those people.

Over time, I built a network of experienced voices: potential customers, former local political leaders, academics and respected experts who helped us learn how the ag world really operated. These advisors helped us understand where people met, what they read, and how reputations were built.

We formalized some of those relationships with equity-based advisor roles:

Equity: Equity aligns incentives much better than cash. For inception-stage companies (just friends and family money or no money raised), I see anything from 0.1% to 1% (exceptionally higher for someone very hands on AND relevant). For pre-seed/seed stage, I would recommend 0.05% to 0.5%. Like for employees, the range is wide and reflects the diversity of commitment and impact advisors may have.
Vesting: 2 years. Your advising needs often change faster than your hiring needs, so it's important to set clear expectations, especially around time commitment, so that if an advisor becomes less relevant, you can mutually and gracefully end the vesting.
Expectations: Regular touch points (e.g., a few calls a month), intros, strategic feedback.

You may need to try 10 relationships to find the 3–5 that really matter. One advisor can often open multiple doors, but it takes time and iteration.

One of the best things we did was organize a yearly advisory summit, where we brought our small group of 6 advisors together for a day of product updates, team time, and dinner. It gave them context, re-engaged their interest, and created shared momentum.

Debugging Sales Like a Technical Problem

Once we got introductions, we had to close them. I didn’t know anything about sales so I relied on the only type of approach that I knew: engineering. After some iteration, this is what it ended up looking like:

Mapped the market top-down. I figured out what dimensions were relevant to classify and prioritize our target customers. I thought about our differentiation and how those differences were valued more by certain types of customer than others. If you don’t have clear product differentiation yet, doing the reverse can also be useful: what do my target sub segment of customers value more than the average customer?
Studied each customer like a case study. I spent days researching each target: what they grew, who they sold to, how they competed, and what might create opportunity for us.
Tested hypotheses like a scientist. I came in with hypotheses, “maybe labor cost matters most,” and refined them in meetings. I asked open questions first to surface blind spots and then closed ones to test.
Reverse engineered the buying process. I tried to understand who else was involved, how and when decisions like ours were typically made, and what role timing played.

It felt like I was learning an undocumented API. But eventually, calls turned into meetings, and meetings turned into contracts. This is still very much the way I approach sales today and I think it helped me embrace sales as a more rational process than I thought it was at first.

Turning Outsider Status Into an Advantage

I expected my background to be a liability. But I learned: people don’t mind outsiders. They mind arrogance. What worked for me was:

Doing my homework. I showed up informed about their business, not just ours.
Admitting what I didn’t know. I made clear I was there to listen and learn.
Being present. I took notes, asked thoughtful questions, and didn’t pretend I had the answers.

The result was that instead of feeling I had to "sell," I had real conversations. One grower told me, “Most startups come in talking and selling. You came in asking.” That farmer has stayed on as a customer to this day.

We didn’t hire a sales manager until we had 12+ paying customers, a repeatable motion across two geographies and a clearer sense of our target customer, pricing, and playbook.

Until then, I ran sales myself, not because I loved it, or because I was any good at it, but because I was closest to the product and the customer’s pain. Doing it directly gave us faster product feedback loops, more authentic customer relationships and a more intuitive understanding of how to scale sales later.

I think it’s a mistake for technical founders to try to outsource legitimacy and trust. In early sales, especially in traditional industries, you are the message and to a large extent you are the product. You only need a few big customers to trust you to acquire the legitimacy you need to sell to the next 10. I think that most technical founders will get there faster if they do the early selling themselves.