The first sales hire: Why most founders get it wrong (and how to get it right)

The biggest mistake I see founders make with their first sales hire? They hire too early.

I've watched this play out across hundreds of early-stage companies. Founders feel overwhelmed by sales, think they're "not sales people," and want to delegate the problem away. So they hire someone to handle what they haven't figured out themselves.

It never works.

Here's the reality: you can't hire a salesperson right out of the gate. You have to actually struggle to sell your software first. Build the playbook. Learn what works. Because if you don't understand your own sales process, how can you possibly coach someone else to execute it?

Don't expect them to solve the problems that you can't solve yourself.

The player-coach analogy

Think about great sports coaches. Almost all of them were players first. They understand the game from the inside out — the pressure, the fundamentals, what separates good from great.

Sales is no different.

If you want to hire somebody, but you've not yet sold your software, it's really hard to then coach the person on how to sell your software. You need that player-coach mentality from the beginning.

Most founders skip this step entirely, assuming sales is just about finding the “right person” who can figure it out — but that’s backwards. Your first sales hire should be leverage, not replacement, and as a founder, your job is to create that leverage by knowing exactly what only you can do, and hiring to take everything else off your plate.

And here's what most founders miss: the founder's job should never be to step away from sales completely. As soon as you step away from sales, you lose touch with what your customers are asking for and what your prospective customers are asking for.

You don't hire to escape sales. You hire to scale what's already working.

When market pull tells you it's time

So, when should you actually hire?

The signal is clear: when you're starting to feel market pull.

For us, we had more inbound demand than we had capacity to handle on calls as founders. We even had our first marketing hire taking sales calls to help. That's your green light — not when you're struggling to find customers, but when you're struggling to handle the ones you have.

But timing is tricky. If you need somebody when you hire them, it's too late. You should have hired them maybe three months earlier to give them some ramp time to learn everything.

We hired our salesperson earlier than we typically would have because we knew we wanted to be aggressive on revenue targets in the back half of the year.

Also factor in the hiring reality: most hiring is 50-50. Fifty percent of people work out, fifty percent don't. So if you need results by a specific date, hire well before that date and have backup plans.

What to actually look for in candidates

The traits that matter aren't always obvious. Here's what I've learned to prioritize:

Competitive spirit matters more than you think. I tend to look for ex-athletes or people who do Ironman's — somebody who's disciplined. It could be weightlifting, CrossFit, intramural baseball, marathons, whatever it is. Competition creates the mindset necessary to thrive in sales.

Great salespeople ask great questions. The number one thing I look for is simple: do they ask questions? If I jump on a call and say, "hey, what questions do you have for me?" — if the candidate has no questions, that tells me they're not thinking or they didn't do their research.

People who do their homework. Do they know who I am? Have they researched mutual connections? Have they done background research on us as a company? Homework is a huge aspect of sales, and it starts in the interview.

People who can ladder conversations. Good salespeople know how to dig deeper. Are they able to ask me a question to get more information before they answer? It's a technique that separates good from great.

When I interview candidates, I ask about their track record: "What was your quota? Tell me about the best quarter you ever had. Tell me about the worst quarter you've ever had." I want to understand what their past roles looked like, how they performed, and how they handle adversity.

The hunter vs. farmer distinction

Not all sales experience is created equal. This is crucial to understand.

If you hire somebody from a massive corporation with a well-known offering, they're not salespeople. They're order takers. They're used to customers saying "I want to buy X product" and then just processing that request. That's very different from actually selling.

In sales, you have hunters and farmers. Farmers pick up deals that marketing delivers — "there are all these deals, I'm gonna go pick them up." Hunters have to go to the woods and actually chase down opportunities.

For startups, you need hunters. People who can create a pipeline, not just manage it.

The experience sweet spot

You want to hire somebody who's gone through the SDR/BDR journey and become a commercial or emerging enterprise rep. Someone five to six years into their career who has real experience but isn't overqualified.

Avoid both extremes. If you're hiring an enterprise rep who sells $500k software and expecting them to go sell $25k software, that's not going to work traditionally. Most reps used to selling seven-figure deals won't go back to smaller deal sizes — they'll get bored and leave.

On the flip side, if you hire somebody fresh out of college, there's a lot of effort on the training side. Most startups just don't have the resources to train people effectively from scratch.

Find someone who's proven they can execute but isn't so senior that your deal size feels like a step backward.

Setting them up for success

Once you hire, the onboarding approach is straightforward: have them shadow you early on.

Get them to shadow you just like you'd onboard an engineer — they're typically paired with another engineer as a buddy. You're their buddy. Make sure you're helping coach them and watching all their sales calls to give feedback.

The progression should be clear: you want to eventually get to where you lead and they follow, and then eventually, over time, they're leading and you're following. When I join calls now, I expect the salesperson to run the meeting — I'm there to help, but I'm not there to structure it.

But never completely step away. Stay involved enough to keep your finger on the pulse of what customers are asking for.

The framework that actually works

After making this hire multiple times across different companies, here's the five-step approach that consistently works:

Step 1: Wait for market pull, not market hope. Don't hire because you think a salesperson will solve your customer acquisition problem. Hire because you have more demand than you can handle. The difference is everything — one is hiring from strength, the other from weakness.

Step 2: Hire for traits that predict success. Look beyond the resume. Competitive people who ask great questions and do their homework will outperform experienced reps who coast. I'd rather train someone disciplined than try to instill discipline in someone experienced.

Step 3: Design comp around what you actually need solved. Ask yourself: Is your biggest issue business development (not enough leads) or sales process management (not enough time to handle the leads you have)? Your comp plan should align with the problem you're hiring to solve. For us, it wasn't lead generation — we didn't have enough time to manage the actual sales process internally.

Step 4: Build the playbook together, don't hand one over. Every company has a sales process, whether it's documented or not. Your job is to extract what's in your head and make it scalable. I expect somebody to be able to go through discovery, document the process, and take ownership of improving it. This isn't about giving them a manual — it's about building something repeatable together.

Step 5: Plan for your sales leader hire (it's different). Your first sales hire and your eventual VP of Sales are completely different roles. One executes, one builds, and one manages. Don't confuse them or expect your first rep to eventually become your sales leader. Plan the transition before you need it.

The bottom line

Your first sales hire isn't about escaping sales — it's about scaling what you've proven works.

Do the hard work first. Struggle through the early sales conversations. Build the foundation. Understand what resonates with customers and what doesn't. Then hire someone to help you do more of what's working.

It's really hard to coach someone on how to sell your software if you haven't figured it out yourself first.

The companies that get this right don't just make a good hire — they build the foundation for a scalable go-to-market engine. The ones that don't end up with expensive lessons in what not to do next time.

Ready to make your first sales hire? Start by asking yourself: Can you already sell your product or service consistently? If not, that's your real first step.