Most sales leaders think they have a hiring problem.
In reality, they have an onboarding problem.  I’ve sat across from sales leaders who were genuinely confused.

“We did everything right,” they told me.
“Great interview. Strong references. Proven track record.”

And yet, 60 days in, that same hire was hesitant. Second-guessing themselves. Missing early opportunities.

What looked like a hiring failure was actually something else entirely.

The ROI of your interview process doesn’t happen in the interview.
It happens in onboarding.

Are you rethinking how you hire and onboard sales talent?

 Explore our Done With You Sales Hiring Program Today!

THE FIRST 90 DAYS DECIDE EVERYTHING

The first 90 days of a sales hire will determine how successful they become.

You could hire the best salesperson in the world—but if you place them in an environment where they’re not set up to succeed, they will struggle too.

I’ve watched confident salespeople slowly lose momentum in those first few weeks—not because they weren’t capable, but because they didn’t yet know what “right” looked like.

When expectations are unclear, even top performers hesitate.
And hesitation in sales shows up fast in the numbers.

The data makes this painfully clear.

Research from Objective Management Group shows that 64% of companies provide less than a 30-day onboarding experience.

That’s not onboarding. That’s orientation.

“When expectations are unclear, even top performers hesitate.”

A study by Paychex found that up to 80% of new hires feel undertrained and dissatisfied with their onboarding experience, putting them at a much higher risk of leaving.

And research highlighted by Harvard Business Review shows that new hires with a strong onboarding experience are 50% more likely to go above and beyond what’s required of them.

Same hire.
Same resume.
Different environment.
Completely different outcome.

Watch this video for more insights:

WHY MOST SALES ONBOARDING MISSES THE MARK

Sales onboarding doesn’t usually fail because leaders don’t care. It fails because it’s treated as a checklist instead of a strategy.

THERE’S NO STRUCTURED PLAN

Many sales hires are handed a laptop, access to systems, and a calendar invite or two—and then expected to figure it out.

That’s not onboarding. That’s survival.

A structured onboarding plan adds clarity where uncertainty kills momentum.
Not just tasks—but clear expectations by week and by milestone.

When people know what success looks like early, they move faster and make better decisions.

SALES IS ONBOARDED IN A SILO

Sales doesn’t operate in isolation—yet onboarding often does.

From the new hire’s seat, it can feel like this:

• Marketing is telling one story.
• Sales leadership is pushing another.
• Customer success is dealing with problems no one mentioned.

They’re left trying to connect the dots; leadership never aligned.

When onboarding brings marketing, customer success, and leadership together, sales hires don’t just learn what to sell—they learn how the entire system works.

“Sales onboarding fails when it’s treated like a checklist instead of a strategy.”

THE PLAYBOOK LIVES IN PEOPLE’S HEADS

One of the most common onboarding gaps I see is undocumented success.

• Processes aren’t written down.
• Buyer insights aren’t captured.
• Winning behaviors are learned by watching—or by making mistakes.

Sales hires shouldn’t have to reverse-engineer what good looks like.

Documented playbooks provide clarity, consistency, and confidence—especially in the first 90 days when momentum matters most.

WHY BUYER-FOCUSED ONBOARDING CHANGES PERFORMANCE

Here’s the biggest miss in most sales onboarding programs:

They teach products and processes—but not buyers.

Salespeople don’t struggle because they don’t know the product.
They struggle because they don’t understand how buyers think, decide, and hesitate.

I often ask new sales hires one simple question:

“What does your buyer struggle with before they ever talk to you?”

Too often, they can list features—but not buyer hesitation.
That’s an onboarding gap.

Effective onboarding shifts the focus:

• From pitching → to understanding
• From features → to buyer impact
• From seller pressure → to buyer confidence

When onboarding teaches empathy and buyer decision-making, performance follows.

ONBOARDING MORE THAN AN EVENT. IT’S A SYSTEM.

Onboarding doesn’t end at day 30.
Or day 60.
Or even day 90.

High-performing sales organizations treat onboarding as an ongoing system:

• Continuous coaching
• Regular feedback loops
• Reinforcement of buyer-first behaviors

That’s how early confidence turns into long-term consistency.

THE REAL COST OF GETTING THIS WRONG

If strong hires aren’t ramping quickly…
If turnover feels constant…
If sales results are unpredictable…

The issue usually isn’t talent.

It’s the environment those people are placed into.

Want to see what a failed sales hire really costs?

Watch the On-Demand Session
In this video, Carole Mahoney, Author of Buyer First and Harvard Business School Entrepreneurial Sales Coach, and Ben Tagoe, CEO of Objective Management Group, share what they have learned about what it takes to have a successful sales and hiring process to avoid the costly mistakes so many make.