The Truth About Hiring Your First Sales Rep

Most founders screw up their first sales hire. Not because they’re dumb. Not because they’re lazy. But because they’re using the wrong playbook.

They look for shiny resumes, fancy logos, and slick talkers. People who sold at Salesforce. HubSpot. Gong. The "big leagues."

Here’s the brutal truth: 87% of first sales hires fail to close a single deal.

If that number doesn’t scare you, it should. Because you’re not just wasting a hire—you’re wasting time, momentum, and your best leads.

I’ve coached over 300 SaaS founders through this exact decision, and what I’ve seen is simple: the reps who crushed it at big-name SaaS companies almost never succeed in a 10-person startup with no brand and no support.

So in this post, I’m going to give you the exact 6-point framework I use to help founders make their first real sales hire—the kind that actually closes deals.

Why This Matters Right Now

If you’re doing $500K to $5M in ARR, you’re probably stuck in one of two places:

1. You’re still doing all the selling yourself. It’s working… sort of. But it’s not scalable. You’re exhausted, and growth is stalling.
2. You’ve hired a rep (or two), and they aren’t producing. You’re confused. They seemed great in interviews. But nothing’s closing.

Here’s the thing: in early-stage SaaS, sales isn’t about “experience.” It’s about fit. You need reps who can sell in chaos. Who can operate without a script. Who don’t melt when there’s no enablement, no brand, and no inbound leads.

This framework will show you exactly how to find them.

1. The Brand Dependency Red Flag

If someone’s only ever sold with a big logo behind them, they’re not ready for your world.

I call this the Formula 1 vs. Go-Kart problem. These reps are used to warm inbound, built-out processes, and buyers who already trust the company. Drop them into your scrappy startup where no one’s heard of you—and they fall apart.

What to ask:

“Where did your leads come from in your last role?”
If the answer is:

• “Marketing qualified leads”
• “Inbound from brand recognition”
  That’s a no. End the interview there.

What you want to hear:

• “I built my own list.”
• “I cold-called 50 prospects a day.”
• “I had to explain our solution from scratch.”

Takeaway: Don’t confuse someone who can close warm inbound leads with someone who can hunt and close cold outbound deals. They are not the same skillset.

2. The “Easy Product” Trap

A lot of reps look like rockstars—until they have to sell something hard.

Selling a basic CRM to sales teams is not the same as selling API-based security software to technical buyers. The more complex your product, the more critical this mismatch becomes.

What to ask:

“What’s the most complex product you’ve sold? How did you explain it to a buyer who had never seen it before?”

Framework:

• Rate your product complexity on a scale of 1–10
• Don’t hire someone who’s only sold products 3–4 points below yours

Example:
You’re an 8 (complex B2B fintech SaaS). Don’t hire someone who’s only sold 3s and 4s (marketing tools or social media software).

Bonus perspective: I have a degree in Biomedical Engineering. I used to sell medical devices to hospitals. That background made it easy to sell complex SaaS as a founder. If you’re technical, you can learn to sell. Your first reps should have that same ability to translate complexity into clarity.

3. The Price Point Mismatch

Selling a $99/month tool is wildly different from selling a $50K annual deal. If your hire hasn’t sold at your price point, they’ll struggle.

Framework:
Here’s a cheat sheet:

What to ask:

“What was your average deal size and sales cycle in your last role?”
If it’s way below your price band, they probably won’t make it.

Non-negotiable: They must have at least 18 months of success selling at your price point.

4. The Support System Shock

At early-stage startups, there’s zero sales infrastructure. No RevOps. No sales engineer. No enablement. No manager holding their hand.

If someone is used to a full go-to-market support system, they’ll be overwhelmed the first time a prospect asks a tough technical question.

What to ask:

“Who helped you with demos? Who handled legal, procurement, or onboarding?”

Red flags:

• “Our sales engineer ran demos”
• “I looped in legal to handle compliance”
• “RevOps built all my reports”

Green lights:

• “I handled everything myself”
• “I had to wear multiple hats”
• “We didn’t have support—I figured it out”

Takeaway: You need Swiss Army knives, not specialists.

5. The Industry Complexity Curve

Domain expertise is overrated. But selling into complex industries? That’s a different beast.

If your customers are doctors, engineers, lawyers, or government buyers, your reps need to know how to navigate nuance.

What to ask:

“Have you ever sold into regulated or high-complexity industries?”
Look for experience selling to intelligent buyers in messy environments. They don’t need to be ex-doctors. They just need to hold their own in the conversation.

Framework:

• Rate your industry complexity (stakeholders, regulations, etc.) from 1–10
• Don’t hire someone from a 3 to sell in an 8

6. The Gut Test: Would You Buy from Them?

This is the most important test. If you ignore the rest of this post, remember this one:

Would you, as the founder, buy from this person?

If the answer is no, move on.

Founders have the best gut checks because you’ve sold the product yourself. Even if you’re not great at it, you’ve closed deals. You know what resonates. You know what’s real.

What to do:
During the interview, ask them to pitch you their last product. Don’t focus on the content. Focus on how you feel.

• Do you trust them?
• Are you engaged?
• Would you write them a check?

If not, don’t hire them.

Remember: In the early days, you're not hiring a rep. You’re hiring the definition of what sales will look like at your company.

What to Do Next

Here’s how to use this:

1. Build your own version of this 6-point test
2. Use it as a scoring rubric for every candidate
3. Trust your gut—and don’t talk yourself into a hire you wouldn’t buy from

Hiring your first rep is a leverage point. Get it right, and you scale faster than you thought possible. Get it wrong, and you stall out for months.

If you want help building the full system—from hiring, to onboarding, to building a founder-led sales machine that actually converts—I built a coaching program specifically for SaaS founders like you.

Want help implementing this in your business?

Join my founder-led sales coaching program: craighewitt.com/coaching

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