When to Hire Your First Salesperson

Rajeev Behera
June 30, 2025
Company Formation
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When you start a company, only you, the founder, should be doing sales until you find you have a repeatable script you can train a salesperson on. I didn't do this at my last company Reflektive, and it was a big mistake.

My 4th employee was a head of sales. I hired them because I didn't know how to sell, and to be honest I didn't want to sell. I wanted to build product. My investors encouraged me to hire this role as well, because to them, more salespeople mean more revenue.

But this isn't actually the case.

I hired him, and quickly realized he couldn't iterate on a sales pitch. Then I realized, sales people don't actually own the content in a sales pitch. They execute on sales pitch content that is already written, usually by a founder or a marketing team.

Sales people are great at running a sales process, hiring a team, managing lead flows, and running outbound campaigns. But at early stages, these things don't really exist, and therefore a salesperson can't add much value.

I realized all this a few years in, when I hit $3m ARR. I looked at the stats, I had closed 70% of the ARR. A junior rep my head of sales hired closed 20%, and my head of sales only closed 10%. I had essentially spent hours managing and talking about things with him, and increased my revenue 30%. I probably could have closed that all myself, and saved myself countless hours in 1x1s with him and saved thousands of dollars as his salary was 2x anyone else's.

When Should You Actually Hire a Salesperson?

After you understand common customer pain points, and after you have a script and a set of slides to go through for each of those pain points. Sometimes it is just 1 or 2 pain points that need to be solved for before you hire a head of sales.

At this point, a head of sales will take this script, and scale it so that new reps can be hired and trained on it, and can parrot the founder's pitch.

This can't happen though, until you figure out how to sell your product and create this script.

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Founder-Led Sales: The Key to Early Success

As a founder, you need to personally experience the sales process to:

  1. Understand what resonates with customers
  2. Identify the real pain points your product solves
  3. Learn how to articulate your value proposition effectively
  4. Build the sales playbook that future sales hires will follow

Don't make the same mistake I did. Embrace the sales role early on - it's one of the most important things you'll do as a founder. Your investors might push you to hire salespeople quickly, but stand your ground until you've figured out a repeatable process.

Remember: in the early days, you're not just selling a product - you're developing the entire go-to-market strategy. And that's definitely not something you can outsource.

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