Every revenue organization wants more top performers.

More sales reps who can create urgency. Who're experts with navigating conflict, holding the line in a negotiation. Delivering the number.

But as sales organizations scale, one of the hardest questions is what to do with exceptional talent once you have it. Do you:

• design incentives that amplify their strongest instincts?

• coach them differently when the pressure rises?

• promote them into management?

And importantly, are the behaviors that make someone an exceptional individual contributor the same behaviors that'll help them lead a team?

This question sits at the center of the latest episode of The Sales Compensation Show featuring Jason Wooten, Head of Finance Operations at ClickUp.

We deep dive into sales performance from a finance and operations lens, with a senior leader from one of the most recognizable software brands in the market.

Jason has led sales teams, negotiated from the buyer side, partnered closely with revenue orgs, and seen how sales behavior changes under pressure. He has a sharp read on the total operating system around performance (from how sellers are motivated, to how procurement reads them, and how companies can inadvertently turn a top performer into a revenue risk).

In this entertaining discussion, Jason and Forma.ai CEO Nabeil Alazzam unpack how senior revenue leaders can build better systems for developing, promoting, and preserving top sales talent.  

We’ve summed up our favorite takeaways below. It’s a great episode to queue up right now, or bookmark on Spotify, Apple Podcasts, and YouTube.

Episode resources

• Connect with Jason on LinkedIn  

• Jason's book recommendation: The 21 Irrefutable Laws of Leadership by John C. Maxwell

Stop treating management as a prize for quota attainment

One of Jason’s hot takes is that he doesn't agree that treating management roles as the natural next step for top sales performers is always the right move, no matter how many sales orgs fall into this.

Here's the clip:

Jason argues that the automatic promotion of top sellers into management can become one of the most expensive, preventable mistakes in a sales organization. Not because top performers can’t become great managers (some absolutely can), but rather he sees that individual contributor success and frontline sales management require different instincts and skillsets.

Great sellers often know how to create urgency, handle objections, stay close to the deal, and optimize their own performance. In a well-designed sales compensation plan, that is exactly what you want. Their personal motivation should align with the company’s revenue goals.

But sales management requires something else.

A strong sales manager has to coach, diagnose issues, allocate resources, build confidence in others, and derive satisfaction from the team’s success. They need to understand why deals are won or lost, not simply how to drag their own deals across the line.

Jason frames this up as the difference between a shark and a shepherd.

Your best closer may have the instincts of a shark: Competitive. Urgent. Wired to win.

But your best people manager needs the instincts of a shepherd: Patient. Focused on the group or collective, and able to make other people better.

Many sales organizations miss this tension.

As Jason acknowledges, when companies promote the shark and expect a shepherd to appear because the title changed, they create risk on multiple fronts; they: 

• remove a high-performing seller from the field,
• backfill the role with someone who may need months to ramp,
• and put a team under a new manager who may not yet know how to coach, develop, or lead through others.

So what looks like a promotion can actually become a subtraction event.

For RevOps and sales compensation leaders, the implication is a sales performance design problem.

If your only prestigious career path is management, you may be pushing top sellers toward roles they do not want or are not built to succeed in. If your promotion criteria over-index on attainment, you may mistake territory quality, timing, or a strong book of business for transferable leadership ability. And if your compensation model rewards individual production without creating a meaningful path for mentorship, coaching, or team leverage, you may be limiting how performance scales.

The question as you evaluate which top sales reps should become managers is actually:

What evidence tells us this person can make other sellers better?

This question requires a more thoughtful view of performance. Jason's recommends looking for the seller who mentors peers without being asked. The person who understands the system behind the win. The rep who can explain why a deal closed and what someone could do differently next time.

This person may not be at the very top of the leaderboard, but they may be better cut out for leadership.

Procurement pressure is a buying signal, not a reason to panic

Jason’s procurement perspective adds another point to the sales talent theme that emerged. As he's noticed, top sales talent is often revealed by how a seller behaves when the deal gets uncomfortable.

In other words, many sellers treat procurement entering the mix as the stage where momentum disappears. But, Jason sees the opposite.

When a senior procurement leader gets on the phone, it's often a sign the deal has advanced further than the seller realizes:

Procurement may introduce commercial trade-offs or escalation dynamics, but to a seller who reads pressure as lost confidence, the instinct may be to discount too early or start renegotiating from weakness.

But procurement conflict isn't the same as deal failure.

It may be the buyer’s way of getting the deal done on terms they can defend.

Ultimately procurement can be a late-stage stress test for the entire revenue system. It exposes whether sellers can hold your business case. It reveals whether managers have coached commercial discipline. It shows whether incentives are encouraging healthy deal quality or teaching reps to survive negotiation by giving value away.

A seller who panics in this stage may not have a pricing problem. They may actually have a problem with confidence, coaching, value articulation or incentive alignment.

High-performing sales organizations ultimately need sellers who can preserve value late in the cycle, when pressure rises and the buyer’s tone changes. And this requires more than a comp plan that rewards closed-won revenue.

It requires manager coaching around procurement moments, as well as clear escalation paths and commercial guardrails that help sellers know what to hold, trade, or protect. And it requires a culture where sellers understand that a hard procurement conversation may be a sign of seriousness, not rejection.

Ultimately make sure you've considered:

Do our sellers know how to behave when the buyer is still interested, but the conversation becomes more adversarial?

Because this is where confidence, enablement, incentives, and frontline leadership all show up at once.

Build a lower-risk path from seller to leader

The good news is that Jason does not leave the top-seller-promotion problem as a critique. He offers sales leaders a practical approach to help.

As he and Nabeil share, instead of moving a top seller directly into full management, you can always create a lower-risk bridge:

In short, you can stress test future leadership with a mentoring role. Wherein you take a little quota away and tie some income to team development metrics instead. This allows for the ability to coach sideways and provides a much better signal to you than quota attainment alone.

• Do they enjoy helping other sellers improve?
• Do peers trust them?
• Can they diagnose performance issues without making everything about how they personally would sell?
• Do they get energy from the team's success?

A trial period like this tests management aptitude before making a more expensive decision. It also protects the seller from the stigma of a failed promotion.

As Jason indicates, in many sales organizations, moving from manager back to individual contributor is treated like a demotion. Even when the person is still talented. Even when the company would benefit from keeping them. Even when the management role simply was not the right fit.

Jason’s view is that companies need to normalize the off-ramp.

If someone tries management and realizes they are better suited to an IC role, that should not automatically become a career scar. It may be the best outcome for all involved. 

If the only way to grow income, status, or influence is to become a manager, the organization will keep pushing strong sellers toward management whether or not it makes sense. A healthier model, however, hgives high-performing ICs a respected path to keep growing without needing to own a team.

This could mean: 

• senior IC tracks
• Mentorship incentives
• Player-coach pilots.
• Team-based development metric
• Leadership readiness criteria
• temporary quota adjustments that let potential managers practice coaching without fully leaving the field.

Overall, companies should design talent movement with the same care they bring to sales plan design.

You wouldn't launch a new incentive plan without modeling the behavior it might create. So why promote a top seller into management without testing out the revenue, ramp, team performance, and retention risks that come with this move?

It's how you preserve sales talent instead of gambling with it.

Sales performance scales through systems, not heroics

As we saw with this conversation, Jason sees sales performance from several angles. He understands both seller motivation and the buyer’s leverage. Plus how quickly people decisions become operating problems as a company scales.

The real takeaway of his leadership points is not just that you should be more careful with promotions or train sellers better for procurement, it's that sales performance doesn't scale through heroics alone.

A top performer can carry a number.
A great manager can multiply a team.
‍
A strong incentive plan can channel behavior.
But a disciplined GTM operating model can protect the business from avoidable talent and revenue risk.

As Jason encourages, there's a huge opportunity for leaders to connect these pieces more intentionally right now.

It'll mean designing compensation plans that reward the behaviors the business actually needs and treating procurement as a moment of value protection, not panic. It'll also mean recognizing that quota attainment is only one signal of future leadership potential, which necessitates building career paths that let great sellers keep growing without forcing every high performer into management.

Want more insights like this? Subscribe to The Sales Compensation Show on Spotify or Apple Podcasts, or YouTube for bi-weekly episodes featuring the revenue leaders behind today’s fastest-growing companies.