This onboarding guide is based on 100s of direct hires I have made, 250 more my peers/close network have made throughout their sales leadership journey. This a collection of what's worked, what hasn't and the final product on this page is a summary of the most effective way to onboard a seasoned sales professional.

This will help with increased sales performance and long term retention of high performing salespeople.

Enjoy....

Hiring a seasoned salesperson can feel like a cheat code.

They’ve done the job.
They know how to sell.
They’re sharp, experienced, and don’t need micromanaging.

And they'll perform at a high clip and stay with me for at least 3+ years.

Right?

Sure, if you onboard them properly.

But here’s the truth:
Most onboarding for seasoned hires is either non-existent, too vague, or way too rigid.
And it's a huge reason why they underperform or leave.

This article is for sales leaders, founders, and CEOs who want to build high-performing sales teams - without burning good people or blaming the wrong problems.

1. Start With Structure - But Don’t Smother Them

Yes, seasoned salespeople are self-starters.
But that doesn’t mean you leave them to fend for themselves or walk them into chaos.

There’s a middle ground.

They need structure without control-freak micromanagement.
Here’s what that looks like:

Clear Expectations

What KPIs matter in your business? What daily rhythm works? What are they expected to achieve in 3, 6, and 12 months? See point 3 for further breakdown/clarification on KPIs.
Yes - they probably presented a 90-day plan in the interview, but now’s the time to break it down, together, into something real.
Start this in Week 1. Lock it in by Week 2.

A Basic Sales Process to Plug Into

What do your best reps do Monday to Friday?
And if sales have been founder-led until now - what did you do?
Walk them through what 20% activities (probably calls, prospecting, meetings, follow-ups, closing) generate 80% of your results. What time of day and day of week has been best for each of those activities? What is the sales script for each - prospecting messages/calls, meetings, follow ups, closing. If you don't have this set in stone yet, that's why you hired a seasoned sales rep, do it together.
Help them map this into their own working style...together. This should be set by week 3-4. They might try some scripts/sales methodologies live then start locking it in as a defined script for now. Of course this will always be adjusted, but let's set an early framework.

Communication Framework

How do you communicate?
WIP (work in progress) meeting once a week? Team catchup weekly/fortnightly? Slack, email, Loom updates? Training Wed mornings? (role plays etc) Again, expectations on this should have been communicated in the interview, but you dive deeper here.
Build a “coach-player” relationship, not boss-employee.

Make it clear from Day 1:
Make them feel comfortable to tell you what's on their mind anytime without fear of being fired - this is sooooo critical!!! If there's something pressing on that person's mind and the first person they call is me, the recruiter, you've failed as a leader! This can be solidified within the first 3 weeks.
And seriously… if the first person they call when they’re stressed is me (the recruiter), you’ve already lost them. Make them feel comfortable about approaching you.

Tools/Systems/Product/Industry: But Don’t Get CRM-Obsessed

Get them set up on your CRM, sales tools, calendars, sequences, templates — all of it. Let them play.
BUT don’t expect a seasoned rep to be a CRM guru. Most aren’t.
They like selling, not admin. So when it comes to CRM show them the 20% activities which generate 80% results (sorry, but logging every call, every touch point, every brown or grey sock the prospect puts on....unless this is automated with AI, it just ain't gonna happen!)
I’ve seen top closers get run out of good businesses because the sales manager was a “CRM Nazi.”

And I’ve seen reps who were excellent at CRM… but couldn’t close to save their life.
You tell me which one adds more revenue. And no you can't have best of both worlds, cause it doesn't exist. Don't do this - Your rep had 8 meetings, 30 calls, 8 follow up calls, it's now 5:30pm, long day, time to go home to family...."oh you haven't logged your calls??" That person will, I repeat, will get burnt out and you'll hinder their performance. At 8am the next day, is a good idea to quickly log their calls, and it shouldn't take more than 10 min (again, look at automating this or getting the sales support/admin person to do it). If in 3-6 months the person is underperforming, you have every right to be a CRM Nazi then!

Product/Industry - I've often said - It is more important to be a great salesperson than it is to be a great product/industry person. OK, so if the salesperson is new to your industry and product, teach them! The basics only. Then drip feed as you go, but by month 3-6 when they start seeing clients, making calls, they'll naturally learn. Have them do 1 on 1s with your engine room - sales support, product team, marketing, finance etc. Don't do it once, have them meet each person 2-3 times in the first 3 months.

Target Market/Getting after it!

Who are we going after? Why? What’s worked in the past? Who buys from us and why?
Get that done in the first week. Again, this was talked about in the interview process, we are now going deeper. And then allow them to get after it. Start making calls, setting meetings by week 2. Seasoned salespeople are doers! Let them do. And they also learn by doing, so set them free and open the flood gates.

Show Them What “Great” Looks Like

Let them shadow your best rep on a few meetings.
Listen to real calls.
Review winning deals.
Show them what a healthy pipeline looks like in your world and point out the process to get there (this was covered in the sales process section).
No fluff. Real examples. Let them see it. Let them feel it.

2. Speed to First Win Matters

Don't worry about the big sales/deal yet.
Forget the closed revenue.

Your first job is to get them a win - fast.

Not a trophy. Just momentum.

Examples:

• A warm-up meeting (even with a client you haven’t spoken to in 12 months)
• An outbound reply - even a rejection (“yes, we’re making progress!”) This sets the tone that rejection is OK (which of course it is). This will ease the pressure and they'll go hard at the input (calls) without fear. 
• A proposal sent
• Moving a prospect from cold to meeting

Small wins build confidence.
And confidence drives performance.

Even seasoned pros want to feel like they’re on the right track.
Celebrate early momentum. It might seem minor but it’s everything.

3. Avoid the Founder KPI Trap

Founders - I’m talking to you. (Sales leaders, you might find some value in this too)

Do not give your new salesperson the same KPIs you hit when you were running sales.

Why?
Because:

• You’re the founder. People take your call.
• You’ve got market authority. Instant trust.
• You work 12+ hours a day because you’re obsessed.

They are not you.
And holding them to your numbers out of the gate?
That’s how you burn a perfectly good hire and convince yourself “great salespeople don’t exist.”

Instead:

• Figure out the minimum effective input required to drive results. Remember, this is just in month 1-3. You will increase the KPIs as they go. Drip feed them. Early wins drive momentum.

Quick story on this - I had a client implement this with an early hire. In his 2nd week, the sales rep called an emergency meeting with the Sales Manager (not me the recruiter, the sales manager). "Mate, my KPIs are too small. I'm here to make sales and make money! Sorry I know it's 2 weeks in but this isn't good enough for me, I need more!"

Sales Manager - Eureka! "Mate, done, I'll up the KPIs!" I guarantee it wouldn't have worked the other way around. Start small, then build up.

• Add a small stretch and build from there over time

Not sure where to start with KPIs?
Ask someone in your industry. Ask AI. Ask me.
But don’t guess. Don’t wing it.

Month 1–3 is about building confidence and consistency, not superhero quotas.

Sales Leaders - With KPIs already in place and set in stone. Ask yourself, are we setting people up for success? Can we drip feed them? If they are what they are, this would've been communicated in the interview process, but now go deep on it and set the expectations.

4. Give Them Professional Autonomy

You want owner-level effort?
Give them owner-level buy-in.

Let them feel like they’re running a business within your business.
This is where the best reps truly shine and commit!

If you’re the founder:

• Show them real business numbers (when appropriate)
• Be transparent about your vision
• Let them in on strategic decisions over time

If you’re a sales leader:

• Share weekly sales data
• Run ideas by them
• Ask them for advice - even if you already know the answer

When they feel like they have a seat at the table, they start thinking like owners.
And when they feel respected, they show up differently.

This isn’t just about performance, it’s about retention too.

And don’t stop there.
Introduce them to the engine room - the team that actually delivers the goods:

• Sales support
• Ops
• Marketing
• Customer service
• Implementation/tech team

If they love the team behind the scenes, they’ll sell harder for them.

I once sold payroll for 3.5+ years.
Not exactly sexy. In fact, I rather watch pen ink dry.
But I stayed and I thrived because I loved the team. I loved the culture! They're good humans.
I wasn’t selling a product.
I was selling on behalf of people I believed in.

5. Don’t Avoid Tough Conversations - Lean In

Sales is a rollercoaster.
There will be dips - activity, pipeline, results.

Letting it slide? Avoiding the chat?
That’s what kills performance and makes average performance the norm.

Set the tone early:

“Hey — just a heads up. We give feedback around here like a pro sports team. It’s never personal. It’s about performance. And I want you to call me out too when I drop the ball too.”

Then, model it: (real life example you can use early on to make tough convos a norm)

“I’ve been off the last couple days. I’ll pick it up and get X done by Friday. Call me out if I don’t.”

That’s ownership.

Then, when their effort drops, you’ve created the space to say:

“I’ve noticed XYZ’s slipped. Is everything OK? Let’s talk about it.”

A wise person once told me, this is one of the best ways to start an uncomfortable conversation - "Hey, we are about to have an uncomfortable conversation, is that ok?" 

You lead by example.
You hold with empathy.
And you build a culture of accountability.

6. Don’t Overcomplicate the Commission Structure

If they can’t explain it back to you in one sentence, it’s too complicated.

They want to know:

• What do I get paid?
• How do I earn more?
• What happens if I overachieve?

Make it clear, fair, and trackable.
Don’t make them guess.
And whatever you decide — lock it in by Week 2.

If you are unsure, email me for ideas/templates on commission structures - alex@athlete2business.com.au

7. Clarity Is the Real Onboarding Superpower

Above all seasoned salespeople want clarity.

 What does a good month look like?
What’s the real sales process here?
How much money can I make and how?
What support do I have (marketing, SDRs, leadership)?
Who do we sell to and why do they buy?
What are our most common objections?
What’s the product sweet spot?

Some of this should’ve been covered in the interview.
But onboarding is where you go deeper.
Make it real. Make it tactical. Remove ambiguity.

Uncertainty kills momentum.
Clarity creates action.

The Onboarding Timeline (Simple but Powerful)

Break it down like this:

Week 1–2:

• Access Tools (CRM, Lead gen etc)
• Shadowing/doing/making calls
• Product/Industry
• Early wins
• Commission/KPI clarity
• Communication rhythms (plant tough/uncomfortable conversations line)

Month 1–3:

• Daily/weekly rhythm getting close to being locked in by end of month 3.
• Early KPIs (input-based) slowly increased and locked in.
• Momentum and confidence - continue to drip feed early wins
• Role play, feedback, coaching
• Product/Industry continued
• 2nd lot of one on one's with engine room.

Month 3–6:

• Raise expectations
• Shift to outcome-based KPIs and clarify the current input KPIs needed.
• Autonomy, ownership, decision-making - build to this.
• Focus on retention, longevity - are they buying into the culture/team? Is there clarity on the task at hand? Sales process and rhythm should be locked in by 6 months.
• They should be full throttle on sales activity now and pipeline should be closing if not already. Check process/if tough conversations need to be had they should feel natural as it's part of culture.

Quick Onboarding Checklist for Seasoned Sales Hires

(Download Onboarding Checklist At Bottom of Page)

• Clear expectations set (KPIs, daily structure, pipeline goals)
• Tools & systems access provided (CRM, sales tech, templates)
• Commission structure explained (week 1–2)
• Communication rhythm agreed (WIPs, open door policy)
• Early win mapped out (meeting, proposal, pipeline progress)
• Integrated with ops/engine room teams
• Ownership & autonomy encouraged (shared data, involved in strategy)
• Performance conversations normalised early
• 30/60/90 ramp structured
• Clarity on key buyer profiles, objections, and product sweet spot

You didn’t hire someone to babysit them. You hired a professional.

Treat them like one.  Give them structure. Give them autonomy.
Give them something to own.

And hold them accountable like a peer, not a junior.

The best onboarding programs aren’t flashy.
They’re clear, consistent, and human.

Get this right and you won’t just make your next salesperson successful.
You’ll build a high performing culture that brings in consistent results.

If you or anyone on your team needs help in onboarding your new sales hire, reach out to our team anytime.

I'm Alex Opacic - founder of Athlete2Business, a recruitment agency specialising in headhunting salespeople with an athlete mindset.