How to Nail Your First Sales Hire (And Avoid a $250K Mistake): Lessons from Jake Walpert

Jake Walpert has built and led sales teams at six different startups, scaling from early chaos to repeatable revenue. He’s driven growth in eCommerce, retail media, and B2B SaaS, and he’s especially passionate about a problem that sinks more startups than you’d think:

Founders botch their first sales hire.

In this episode of Knocking to 10, Jake shares why your first AE is the most pivotal hire you’ll make—and how to set them (and your startup) up for long-term success.

Why Most Founders Hire Their First Rep Too Early

Founders love to chase scale. But Jake’s seen the same pattern over and over again:

“They hit $500K in ARR and think it’s time to hire a rep. But all their deals came from referrals or friends. That’s not product-market fit—it’s founder-market fit.”

Key lesson: Don’t make your first hire until you’ve closed at least 5–10 cold deals yourself—without relying on your network. That’s how you know your process works.

What Founders Get Wrong About Onboarding

You’ve made the hire. Now what?

Too often, founders drop a new rep into the deep end and hope they figure it out. Jake’s advice?

Build a structured onboarding program that includes:

• A fully documented sales process
• Clearly defined ICP and buyer personas
• Tested messaging that resonates with your best-fit customers
• A daily check-in cadence for coaching, not just metrics

“You need to take what’s in your head and get it into theirs. If you can’t teach it, they can’t sell it.”

How to Spot a Great First Sales Hire

What traits should you look for? Hint: it’s not logos on a resume.

Jake’s ideal first hire is:

• Tenacious and scrappy
• A systems thinker
• More entrepreneurial than polished
• Excited to build something messy

Avoid: big-company sellers who are used to inbound leads, layered ops teams, and buttoned-up processes. You need someone who thrives in ambiguity and can create structure—not wait for it.

Rethinking Free Trials: Why “Hands-Off” Isn’t Working

Jake also shared how he revamped a broken trial process at a previous startup:

• Too many unqualified users were let into free trials
• Trials were poorly supported, leading to confusion and churn

His fix?

• Introduce a kickoff call to set expectations
• Define trial success metrics upfront
• Maintain regular touchpoints during the trial period

The result? Trial-to-paid conversion jumped from under 50% to 73%.

Cold Emails Without CTAs? Yup, It’s Working

Jake’s favorite outbound tactic right now? No call to action.

Instead of pushing for a meeting, his team sends emails that demonstrate expertise, provoke reflection, and create curiosity.

“Buyers don’t want cheesy meeting requests. They want to hear from someone who understands their space and can teach them something.”

It’s counterintuitive—but it’s working.

The $250K Mistake You Can’t Afford

Hiring the wrong AE can cost a startup $250K+ in salary, lost revenue, and wasted time.

Jake’s final advice for early-stage founders?

• Qualify yourself first. Close deals without relying on your network.
• Codify your process. Know your ICP, personas, messaging, and win rates.
• Hire for initiative. Look for reps who build, not just follow.

“You don’t need a perfect rep. You need someone tenacious, adaptable, and ready to build the process with you.”— Jake Walpert

Listen to the Full Episode

🎧 Knocking to 10: Jake Walpert on Building Sales from Scratch and Avoiding Early-Stage Landmines

Watch on [YouTube] or listen on [Spotify].

Follow Jake on LinkedIn to keep learning from a pro who’s been in the trenches.

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