The Stakes: Why Most Companies Fail at Onboarding Salespeople
If you’re reading this chapter because you’ve just hired your first truly elite-level salesperson, congrats. Maybe.
It's not time to celebrate yet. Now, you need to get them up to speed and contributing to growth faster than anyone you've previously hired. The cost of a failed sales hire is astronomical—we've already covered this.
But let’s talk about an even bigger risk: losing an elite salesperson because you botched their onboarding.
Why are the risks greater? For one, basic economics, baby.
Chances are good that you used a recruiter with a fee you don't typically spend to fill other sales roles. You've likely committed to unique and additional incentives, including more cash than usual, and these additional cash expenses are noticed by your "friends" in finance and human resources.
But wait, there’s more for you to consider before you decide to skip this chapter.
As you sought alignment from Finance, Human Resources, and the C-suite to abandon the conventional hiring process and compensation structure to support your unconventional approach, they all made a mental note —if you've made a bad bet, your credibility will suffer. No pressure, huh?
Real World Onboarding Realities
When CEOs hire me to assess their sales teams, I conduct stakeholder interviews, which include talking to every single salesperson on the team. Often, I learn that the sales leader is contributing to the team's underperformance because they don't do onboarding well.
Often, the reps will tell me there was no onboarding. I share this feedback with the sales leader who is initially defensive and points me to the practice of having new hires shadow more tenured reps. If that’s you and your approach to onboarding, then you don't have proper onboarding.
Here’s an example–when I interview salespeople, I’ll ask, "Tell me about your first day." The reps will respond with things like:
"It was a week after I started before I received my computer."
"I spent the first day trying to set up my laptop."
"The people I was supposed to meet with didn't show up for the meeting."
“I spent the first day consuming useless HR videos on safety and policy.”
"I didn't have a schedule for my first day. It’s like they forgot I was starting."
This is amateurism if you're trying to build a category-defining sales team full of elite-level salespeople. It signals to an elite salesperson that the sales leader hasn't turned pro (yet).
Elite Salespeople Demand A Proper Onboarding
Imagine a hospital bringing on the top heart surgeon and scheduling their first surgery without:
Taking the time to ask the surgeon what medical devices and equipment are required to perform each procedure.
Creating space for the surgeon to meet the rest of the surgical team and show them how to support them during the surgery.
Making sure the rest of the hospital staff was prepared to support this elite surgeon and their expectations of the hospital.
It would be nonsensical for a hospital to hire an elite surgeon and not properly onboard them, so why wouldn’t an elite salesperson need appropriate onboarding, too?
“But Nigel, why can’t an elite performer hit the ground running?”
The best salespeople have options.
Onboarding for elite salespeople might look different from onboarding an average or junior salesperson, but it's still required. If you skip it, intending to speed up an elite salesperson, you are actually slowing them down—which will frustrate them, you, and others in the business.
Just like the heart surgeon that doesn’t need and won’t tolerate redundant “How to do a surgery” training, elite salespeople still need to know who to turn to for certain requirements of the transaction. Things like:
How we document opportunities and customers
Pricing, deal negotiation, and execution
Customer Success
Product knowledge mastery
Company culture, structure, policies, etc.
If they feel like your company is disorganized, slow-moving, or lacks the necessary support to set them up for success, they won’t hesitate to walk away. And if they leave, they won’t just take their talent elsewhere—they’ll take the lessons they learned from your company to your competition.
How To Properly Onboard Elite Salespeople
Hiring an elite salesperson is a moment of transformation for your company. But the moment they sign the offer letter, the clock starts ticking. Get the onboarding process wrong, and you risk losing them before they ever make an impact. Get it right, and you unlock their full potential faster than your competition even knows what hit them.
In every business function, employees need time to familiarize themselves with their new environment, absorb company culture, and integrate into existing workflows. Elite salespeople require this, too, but elite salespeople are different. They are potential revenue engines from day one.
Their onboarding isn’t about easing them in—it’s about accelerating them to peak performance.
If you think you can treat their onboarding like a standard new hire orientation, you're making a costly mistake. Elite salespeople are measured by and expected to contribute immediate, tangible results. The sooner they can start producing, the more likely they are to stick around, stay engaged, and drive revenue growth.
Elite vs. Untenured Salespeople: Key Distinctions in Onboarding
Most companies mistakenly lump elite salespeople into the same onboarding process as junior or average sales reps. That’s a fatal error. Elite salespeople don’t need basic sales training, hand-holding, or generic onboarding checklists. They need rapid integration, immediate access to the right tools, and a fast path to making an impact.
The bottom line? Onboarding an elite salesperson is about acceleration, not education.
Onboarding Starts the Day They Sign the Offer Letter
Most companies make the mistake of thinking onboarding begins on the elite salesperson’s first official day—just like every other new hire. That’s too late. Why?
Most new hires, including salespeople, will immediately provide notice to their current employer. The notice will inform them of their resignation and provide them with a two-week notice. It’s not that simple for elite salespeople.
Unlike most new hires, elite salespeople are earning large commissions and bonuses. These large sums of money have already been earned for their past performance but may not yet be paid to them—commissions on large deals, quarterly bonuses, etc. The payment is coming at some point in the future but hasn't yet been paid.
They are handcuffed.
It’s a high-class problem unique to elite salespeople, but its real. Its common for the sums to range from $10K to $100K. They’ve already earned the money, so walking away is foolish.
They will sign your offer letter now but might not resign until after the money has been paid, which might be 60 days from now.
If you sit around for two months waiting on them to resign, you’ve already lost valuable momentum, and the rep has spent weeks waiting, wondering, and potentially second-guessing their decision.
Your onboarding process must start the moment they sign the offer letter.
Here’s what should happen immediately:
Pre-Start Communication: The hiring manager should send a welcome message, reinforcing excitement and setting expectations.
Pre-Start Ramp-Up Materials: Send them product overviews, sales playbooks, competitive analysis, and market research so they can start absorbing key insights before day one.
Tech Setup: Ensure their CRM access, email, phone, and sales tools are fully configured before they start. That way when they start, day one is more productive. Nothing kills momentum faster than technical delays.
Internal Introductions: Connect them with the top performers on your sales team before their start date to build camaraderie and alignment.
Early Wins Plan: Set clear, published, controlled, and mutually agreeable expectations for their first 30, 60, and 90 days. More on this in the next chapter.
Expanded Onboarding Plan: The Five Phases
The length of your onboarding process depends on your sales cycle and other factors unique to your business. Whether it's one week or one month, you need to onboard your newly hired elite salesperson in five phases.
Phase 1: Pre-Boarding (Before Day 1)
Company & Industry Knowledge: Send comprehensive materials so the salesperson can begin learning in advance.
Technology Setup: Ensure CRM, emails, and sales tools are ready.
Team Announcements: Announce the hire internally so everyone is prepared to welcome and support them.
Corporate Compliance: Take care of all the necessary but time-consuming Human Resources tasks during Pre-boarding. Health insurance, corproate compliance training, etc.
Phase 2: The Kickoff (On Day 1)
High-Impact Orientation: No generic HR lectures. Focus on key sales strategies and customer expectations.
Observing Top Reps: Have them watch the best on the team in action. I think it’s best to have them watch recordings of past selling conversations vs. real-time observations.
Phase 3: Ramp-Up (Up to 30 Days)
Daily Coaching & Feedback: Frequent check-ins to discuss and refine sales approaches.
Pipeline Ownership: Start assigning accounts and opportunities.
Phase 4: Performance Testing (Days 30-60)
First Sales Milestones: They must begin closing deals or achieving set targets established in their 90 day success plan.
Self-Sufficiency Benchmark: If they’re struggling, reassess if they’re truly elite or if you and your company are the limiting factors.
Phase 5: Full Ownership (Day 90)
Result Achievement: Full accountability for results established in the 90-day success plan. This could include closing deals but might be higher in the funnel metrics like meaningful conversations or pipeline creation metrics.
Strategic Selling: Expect them to contribute to improving the sales process for you and the rest of the team.
Final Thoughts: The Cost of Getting This Wrong
Elite salespeople don't wait around. They will leave if they aren't closing deals in their first few months. And when they do, they take valuable market intelligence and your competitive edge with them.
Your onboarding process isn’t just about ramping them up—it’s about proving to them that they made the right choice in joining your team. The best sales leaders treat onboarding like a high-stakes investment because that’s exactly what it is.
Now, the question is: Are you setting them up to succeed or setting yourself up to fail?
