Why your sales hire Is struggling—and how to fix it

When one of my clients hired their first salesperson, everything looked great on paper.

They were excited—relieved, even. After months of founder-led sales, it felt like they finally had someone to take things off their plate.

A few weeks later, the panic started.

The founder started wondering: Did I hire the wrong person?
But the real issue wasn’t the hire. It was the lack of a playbook.

Struggling to Hire the Right Salespeople? 

Stop wasting time on the wrong hires. With the Done-With-You (DWY) Sales Hiring Program, you’ll attract, hire, and onboard top sales talent—faster and with less risk.

• 91% success rate
• Reduce hiring time by 75%
• Proven, data-driven process

READY TO BUILD A HIGH-PERFORMING SALES TEAM? LEARN MORE ABOUT THE DWY SALES HIRING PROGRAM TODAY!

The Founder’s Blind Spot

This happens all the time—especially in early-stage companies and small businesses.
The founder has been selling successfully because:

• They built the product or service
• They know the buyer inside and out
• They’ve lived every version of the pitch
• They are the story

So they assume that someone else can just jump in and replicate that, no matter how talented.

But that’s not how it works.
New hires aren’t you.
They didn’t build what you built.
They haven’t had hundreds of conversations with buyers.
They don’t know which objection requires a story, a stat, or a strategic pause.

That’s when I told my client: You can’t expect someone to sell your vision if you don’t give them your playbook.” Document it. Break it down. Share it.

Want to see what buyer-first onboarding really looks like?

Watch this month’s video breakdown:

What We Did Differently

We returned to square one—and built onboarding from a buyer-first lens. Instead of starting with product features, we started with the buyer’s world:
What problems are they facing right now?
What language do they use to describe those problems?
What outcomes matter to them?

From there, we layered in:
✔️ Real call recordings (wins and losses)
✔️ Sample emails and responses
✔️ A 30-day milestone plan
✔️ Clear definitions of what “good” looks like

And it worked.
The rep turned things around quickly.
Because they finally had context. Direction. And confidence.

You Don’t Need a 90-Day Manual.

Here’s the good news: building a playbook doesn’t have to be overwhelming. It just has to be intentional.

If you’re onboarding salespeople (or thinking about it), start here:

1. Start with your buyer.
Define their problem in their words before you ever pitch your product.

2. Build in micro-chunks.
Don’t overwhelm new hires. Sequence the learning in layers—problem, solution, then differentiation.

3. Share real-world examples.
Let them hear what buyers sound like. Let them feel what a successful conversation flows like.

4. Personalize based on skill gaps.

Use assessments or coaching to guide where each person needs support.

If your sales onboarding plan is:
“Shadow me for a bit and figure it out”—
You don’t have a plan. You have a revolving door.
And that revolving door is costing you:
💸 Time
💸 Talent
💸 Trust (with your buyers and your team)

Give your hires the tools they need to succeed.
Because talent doesn’t fail—systems do.

If you are a founder who wants to find and convert more paying customers

—and build a business that lasts—join me at INBOUND25.

I’ll be leading Founder Led Sales: Best Practices to Find and Convert Paying Customers, where I’ll share the exact methods I use to help founders master the sales skills they need most.

Register now — your future customers are waiting.