Lessons Learned From Being a Founding AE

If you have hung around the Sales Players community for a while, you already know I have a soft spot for early stage companies.

I like messy environments. I like figuring things out on the fly. I like being close enough to the founders to see what is happening behind the curtain.

But I get asked all the time about whether it's a good idea to take the plunge and become the first sales hire at a brand new startup.

Instead of giving you a list of pros and cons, I want to tell you the story.

This is the story of when I stepped into a founding account executive role. You can decide for yourself if it sounds like an adventure you want to sign up for or if you are better off joining a later stage rocket ship.

How It Started

At the time, I was living in Austin and working as a middle manager for a big Bay Area unicorn. The money was good. The team was great. Most people would have stayed put.

But I wanted to get back into closing enterprise deals. I had watched enterprise reps pull in massive commission checks and I knew that if I ever wanted a shot at leadership on the enterprise side, I needed time in the seat.

One July afternoon I was riding my mountain bike at City Park in ATX (If you know, you know)

I ran into another rider and we started talking. I told him what I did for work. He told me he had just raised money for a new startup and was looking for his first enterprise seller.

A week later we met for coffee downtown. He brought his co-founder. They walked me through the product and the vision. They were technical founders with an impressive resume and a successful exit behind them.

At one point they slid a napkin across the table and asked me to write down the number I would need to join them.

I wrote down a number that was about forty percent higher than what I was making because if you are going to take a big swing, you need some cushion. They did not quite match it, but they came close.

A few days later I signed the offer. There was a chunky equity package on top of the base and OTE. I did not fully understand how the cap table worked at the time, but the idea of owning a piece of something from day one seemed too good to pass up.

Being as early stage as we were, with a limited budget for marketing, my pic was used on the homepage of the website.

What Day One Looked Like

I was employee number seven. The office was in a shopping center in West Austin. Most of the team were engineers. A few days before I started, they had hired a head of demand generation who turned out to be one of the best parts of the entire experience.

She knew how to build pipeline on a shoestring budget and she and I worked side by side from day one.

The founders asked me which CRM they should buy since they did not have one. We set up HubSpot and loaded it with contacts.

By day two I was digging through the founders email and phone contacts looking for anyone we could reach out to. It was not glamorous, but it worked. We also ran intros through our investors and landed our first onsite visit with a local tech company. The early traction was real but every single deal felt like a fight.

We built the first proposals from scratch. We debated pricing until after dark. I learned more about usage based pricing in two months than I had learned in the previous five years. I had no SDR and no sales engineer. The founder acted as my SE because the product was deeply technical.

I spent nights and weekends learning terminology from the cloud computing world just to keep up in customer conversations.

Where Things Got Hard

If all of this sounds exciting, it was. It was also incredibly stressful. The founders eventually asked me to present revenue updates during the monthly board meetings.

I had never presented to a board before. It was intimidating to sit in a room with people who had put their own money into the business and deliver updates on numbers that I did not set in the first place.

We actually closed a number of strong deals, including a two hundred thousand dollar annual contract with a large tech company. But the founders had promised aggressive growth targets to their investors and the pressure trickled down.

At the same time, they were burning out. Some days I would find out they had gone home early or that they were at the pub around the corner while I was grinding through calls and emails. The imbalance turned into resentment. The truth is simple. For a founding seller to succeed, the founders have to care about selling more than you do.

How It Ended

After almost a year of nonstop work, inconsistent leadership, and heavy pressure from the board, I burned out completely. One day I walked in, told the founders it was time for me to move on, and left. I never recommend quitting without another job lined up. It put me in a tough position for months. But it was the right decision for my mental health.

About a year and a half later, the company was acquired quietly. I never learned exactly what I walked away from (I did not vest any of the equity I was granted).

What I do know is that the experience was worth more than the equity. A year in a startup at that stage feels like five years of real world business training. I learned how to build a sales motion from scratch, how to work with technical founders, how to price a product, and even how to write simple Python scripts since the founders insisted that I learn the basics.

Should You Do It?

If you want variety, growth, and exposure to every corner of the business, being the first sales hire can be the most rewarding chapter of your career.

It can also be the most draining. You are a seller, a marketer, an operator, and a part time founder. If the idea of wearing all those hats excites you, it might be a perfect fit.

If you ever find yourself evaluating a founding sales role, reach out.

I can help you look at the company's financials, assess the risk, and figure out if the opportunity aligns with what you want in your career.

Quick Podcast Update...

It's been a while since I've put out any new podcasts episodes. I recently started in a new role and company, in a new category of tech and I've been "drinking from the firehouse."

I'm hoping to get back to doing regular guest interviews, but it's been challenging to balance onboarding/ramping, family stuff, 1:1 coaching, and work travel.

I'll most likely pick things back up in early 2026.

As always, thanks for your support and for being part of the Sales Players community!

-Jesse

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