Your First Sales Hire Will Make or Break Your Startup: Wisdom Shared from Three Founders

I was under intense pressure to hire. Sound familiar?

My recent panel discussion with three experts -

Machiel Kunst

from Bluebird Recruitment, @Caroline Korteweg from UnCover, and @Jonas Larson who built and sold Pento - revealed some not so obvious truths about making your first sales hires. But the story that blew my mind was Machiel's confession about his worst hiring mistake.

He ignored his gut about a candidate. But then he saw the guy's LinkedIn posts. They were brilliant. Articulate. Insightful. Everything you'd want from a sales hire. So Machiel pulled the trigger and hired him, specifically mentioning those posts as the deciding factor.

Then he discovered the truth: Every.Single.Post. was plagiarized.

The hire lasted less than his probationary period.

Want to learn from founders who've navigated these exact challenges? Join our free community at Founder Led Sales where we share frameworks and wisdom from other founders on the same journey.

The Big Corporate Name Trap

Caroline shared another pattern I see constantly: founders getting seduced by impressive resumes. Her story involved watching a founder hire someone straight from a big corporate environment with "beautiful, beautifully made decks" and that blue-chip background they thought would bring instant credibility.

The result? Total failure. Why? Because this person "didn't know how to get down and just put his teeth in it." They couldn't handle the scrappy, figure-it-out-as-you-go reality of startup sales.

Jonas made a similar mistake with his first head of sales. Strong performer from a big company, but when thrust into a leadership role at a startup, they ended up hiring "way too many people" and "way too many junior salespeople." The correction took 6-10 painful months.

Here's what all three experts agreed on: startup experience isn't just preferred, it's mandatory when making an early sales hire.

When You're Actually Ready to Hire

So when should you make that first sales hire? The signals are clearer than most founders think:

Machiel's criteria: You've personally closed deals from cold outreach (not just your network), you understand your ideal customer profile, and you have at least a sense of repeatability. Most importantly, you're not hiring someone to figure everything out from scratch.

Jonas's reality check: His calendar was literally full of quality meetings. Not just any meetings, but quality prospects. As he put it, "there aren't many things that are more important in your early days than for me as the non-technical co-founder, to speak to prospects and customers pretty much all day, every week."

Caroline's wisdom on when to hire more sales people: Wait until your first hire or two becomes comfortable with the process and starts recognizing patterns. When they can spot the regular objections, understand the ICP, and know which customers to avoid.

The thread connecting all three? You need to do the heavy lifting yourself first. You can't outsource figuring out product-market fit.

The Profile That Actually Works

Machiel's seen hundreds of first sales hires. His six must-haves are non-negotiable:

1. Passionate about your mission (their eyes should light up when you tell your founding story)

2. Startup experience (corporate doesn't translate)

3. Prospecting excellence (they need to create pipeline from scratch)

4. Proven success as an AE

5. Challenger sale profile

6. Understanding of your deal philosophy (similar complexity and deal size)

But here's what surprised me: Jonas's best early hire came from an account management role, not sales. Why did she succeed? "She had way more empathy for the customer," which was crucial in the early days when you need to learn from every conversation, not just run a playbook.

Caroline emphasized two traits above all: customer obsession and resourcefulness. At a startup, you're going to do things you didn't expect to do because you're part of a small team with limited resources.

Keep Compensation Simple

The compensation mistakes were telling. Jonas admitted to overcomplicating things by copying playbooks from larger companies too early. Quotas, complex commission structures, the whole nine yards. His advice? Keep it simple: base plus 10-15% commission on every deal closed.

Caroline used 15% commission plus equity. Machiel advocates for a 50/50 base-to-variable split because "you're hiring people that bet on themselves."

But here's an important detail Jonas learned the hard way: be careful about paying full commission immediately on annual deals. When deals fail implementation or churn after four months, you've paid out commissions on revenue you never actually collected.

The Two-Hire Strategy

Multiple panelists emphasized something counterintuitive: if you can afford it, hire two people at once. Why?

As Jonas explained: "Only hiring one is also a risk. It doesn't properly test whether it's the person that's successful or unsuccessful or whether it's the market or the product."

When he hired two, the person he ranked second ended up far outperforming his first choice. Had he only hired his top pick, he would have learned the wrong lessons about what works.

Trust Your Gut When Things Go Wrong

Caroline's advice on course-correcting was extremely practical: "If your gut says something is off, if you need to pull people and push people to do things, if they're saying it's not them, it's the other person or the customers, then at some point you really got to cut it off and do it quickly."

The energy test is real. Are they giving you energy or taking it? The best salespeople almost dismiss the goals you set for them… they're trying to overachieve whatever target you give them.

When there's doubt, there is no doubt. Everyone who's had to let someone go says the same thing: "I should have done that sooner."

Your first sales hire can unlock massive growth or burn precious runway. Choose startup experience over prestige. Prioritize customer obsession over slick presentations. Keep compensation simple. And remember: you can't outsource the hard work of understanding your customers.

Ready to dive deeper into founder-led sales strategies and learn from founders facing the same challenges? Join our community at Founder Led Sales for frameworks, resources, and insights from founders who've been exactly where you are.

See you soon!

Seth