It takes a huge group of cross-functional people to get sales compensation planning right—RevOps, Sales Ops, finance, HR, legal, systems, and of course, the field. But when you’re part of this group, it can feel less like “alignment” and more like whack-a-mole with spreadsheets.

In a recent panel we hosted leaders from Stripe, ClickUp, BD, to dig into what it takes to make sales compensation planning work in the real world: how to organize ownership, when to start, what data to watch, and how to keep the field engaged without opening the floodgates to chaos.

We assembled some incredible guests, including:

• Tanu Agrawal, Global Head of GTM Planning & Central Operations, at Stripe,

• Jason Wooten, Head of Finance Operations at ClickUp, and

• Alex Armbruster, Vice President, U.S. Finance & Global Commercial Operations, at BD.

Below we've collected their practical takeaways for those who want fewer fire drills and more leverage from their sales compensation plans—with clips where you can see the thinking unfold in real time.

Ensure you're making sales compensation planning a cross-functional, RevOps-led sport

All of the leaders on our panel agreed: there is no single “right” owner of sales compensation or incentive planning. That is, Finance, RevOps, HR, and sales ops can each own pieces. What ultimately matters is that:

• The outcomes are clear (growth, fairness, predictability)

• The decision rights and responsibilities are explicit

• The right stakeholders are in the room early

Ultimately, you can think of RevOps as the hub, not the hero

At Stripe, Tanu’s team doesn’t formally own comp design, enablement, or finance. Instead, they act as the hub for GTM planning; bringing together HR, finance, regional ops, sales leadership, compensation, owning policies and the overall planning rhythm, and ensuring strategy and operational reality really meet.

Jason at ClickUp plays a similar role from the finance side—not as the comp plan owner per say, but as the connective tissue between sales compensation, revenue targets, and the field. He's ensuring:

• Regular contact with reps and managers, not just execs,

• Translaltion of the company’s North Star and revenue goals into language front-line leaders can act on, and

• That the reps with the best insight are heard.

Finance as growth partner, not cost cop

Alex shared his function rolls into finance but does own sales ops, territory management, and sales incentive planning. He emphasized that this only works because finance views comp as a force multiplier, not a line item:

"My role has always rolled into finance, but supported sales very explicitly. And I've also owned both the revenue planning as well as the sales operations aspects. What I've come to really appreciate about that...is a finance leader that views sales and sales incentives and quota and territory planning that can be a force multiplier...
Not viewing commissions as just a big expense, but how can we leverage those kinds of things to drive more revenue, increase impact broader populations for us, reach more patients. I think that becomes a really strong partnership that way."

So what practical moves can you borrow from our leaders?

• Create a simple RACI for sales compensation planning, quota setting, territories, and policies, and be clear on your milestone dates for decisions.

• Have RevOps or Sales Ops explicitly act as the hub across finance, HR, systems, and the field for this planning.

• Get agreement at the exec level that commissions are a strategic lever, not just a cost to minimize.

Think of your annual sales comp planning like a brisket, not a frozen dinner

One of the biggest myths the panel called out: that sales compensation planning is an annual event.

Jason’s analogy nailed it. Too many companies treat the comp plan like a frozen family-size meal: throw it in the oven in Q4, pull it out on Jan 1, and hope it’s edible:

In reality, effective sales comp planning is more like a long, slow cook than “set it and forget it.”  

Jason shared that about 80% of the work happens before go-live, but you still have to monitor temperatures (attainment, pipeline, macro changes), refuel (tune SPIFFs), and adjust as conditions change. He also discussed how quarterly incentives and SPIFFs double as a testing ground for next year’s plan metrics.

Start planning earlier than feels comfortable

Stripe runs on a Jan–Dec fiscal year. They’re already thinking about FY27 in Jan/Feb of FY26.

Why so early? This allows them to lock metrics, targets, and new role definitions early. Once those are baked, it becomes too late to make meaningful comp changes, and anything that misses the window gets pushed to the following year by design.

Tanu described this as building a “circadian rhythm” for planning. This way, everyone knows when metrics lock, when quotas are finalized, and when changes are off the table, meaning you can realistically operationalize your plan as it's set on a milestone timeline that was communicated in advance.

Do retros in real time, not six months later

Further, instead of waiting for a big retro in February, we learned Stripe runs micro-retros after each planning stage:

• Headcount planning

• Territory design

• Quota setting

• Comp and policy decisions

This way, the pain of each phase is fresh and the feedback is more specific. The org still compiles a full retro later, but they’re not relying on foggy memories.

Use SPIFFs and in-year incentives as a test lab

ClickUp treats quarterly incentives and SPIFFs as a sandbox for future sales compensation plan changes:

• Want to introduce a new metric? Test it in a SPIFF first

• See how it performs across segments, whether reps understand it, and how easy it is to operationalize

• Promote it to the main plan only after it’s proven and measurable

Taken together, the brisket analogy and these process choices point to the same operating principle: your sales compensation plan is never truly “done”— it’s continuously managed.

Let the curve reveal the truth (then fix broken metrics)

While you certainly can’t run data-driven sales compensation planning on vibes, our panel spent a lot of time on what data actually matters once the plan is live.

Alex leans on a handful of core views, like:

• Attainment histograms: how performance clusters by role/segment,

• Pay vs. target comp distribution: how many are under-earning vs. over-earning, and

• Pay-mix “fingerprints”: where reps are actually earning—base, measure 1, measure 2, SPIFFs.

In this clip, the group talk about using histograms and pay distributions to read field sentiment, pressure-test fairness, and even predict retention risk:

Note Shawn's useful visual trick: draw a line for company performance on the chart and look at where the curve sits. If the company hits plan but most reps miss, you have a bigger problem in your sales compensation strategy.

As Tanu shared, trends in quota relief add another layer:

• Growing quota relief requests equates to something being structurally off in quotas, territories, or policies, and

• Clustered relief (same segment/region) = design issue, not “a few squeaky wheels”

Tanu uses these two signals specifically as policy feedback. That is, when certain patterns repeat, Stripe adjusts policies rather than hacking one-off fixes into the comp plan.

Of course, sometimes the problem isn’t the distribution—it’s the metric itself. Which brings us to...

When a comp metric is broken, rewrite the plan

Jason shared a lesson from a prior design: paying on ending/theoretical ARR in a ramped, competitive SaaS environment.  

On paper, this seemingly aligned with long-term value. But in reality, it led to overpayment and required layers of controls. Eventually, the team rebuilt the sales compensation plan around measures that better tracked real cash and deal quality, and kept OTE and earning potential intact.

The deeper takeaway here? Don’t be overly precious if you discover a bad metric. If the plan incentivizes the wrong behavior, fix the metric, not just the edge cases.

• In younger, scaling companies, this kind of re-platforming is sometimes the only best move—as long as you bring data, not just opinions, to the table.

• As Jason shared, be sure to communicate that you’re changing how people earn, not capping what they can earn when they win the right way.

The metrics checklist to review regularly based on our discussion?

• Attainment and payout distributions by role/segment

• % of reps above/below target comp

• Volume and pattern of quota relief/exception requests

• Plus keep an eye on deal mix and pay-mix fingerprints (i.e.: how are people potentially “gaming” the system?)

‍Don’t undercut your strategy with caps and “mega deal” anxiety

As we touched on toward the end of the discussion, sooner or later, every org has the same uncomfortable conversation: what if a rep lands a massive, windfall deal?

Do you cap them? Discount the rate? Change the rules mid-stream?

Jason cut to the heart of it: capping pay can backfire (and he's not a fan):

Jason shared he’s seen top reps earn more than the CEO in certain years because of a few huge wins, and it wasn’t a problem. If the customer is credit-worthy, the sales cycle was diligent, and the deal passed the usual deal-desk rigor, paying the full amount builds trust and keeps the entire team chasing big opportunities.

Shawn connects this to growth strategy and sales compensation design:

• High-growth organizations that depend on large enterprise wins can’t, in good faith, both tell reps “go hunt whales” and then cap their harpoon.

• If you already have a strong deal desk vetting structure, terms, and risk, you’ve already controlled most of the downside.

• Caps and punitive mega-deal rules often send a louder meta-message than leadership intends: “We say we want big deals, but we don’t really want to pay for them.”

For Sales Comp and RevOps leaders, this is a culture-defining choice:

• Paying mega deals in full becomes a living case study for everyone else: “This is what’s possible if you execute our strategy well.”

• Capping mega deals becomes a story too—just not the one you want told on Slack and in ride-alongs.

If you truly can’t stomach uncapped exposure, at least:

• Be transparent about how mega deals are treated, before the year starts

• Pressure-test that policy against your stated growth strategy

• Involve deal desk and finance so that risk is managed in the deal, not retroactively in comp.

Bringing it all together

If you’re in (or about to be in) planning mode, here’s the short list of moves to steal from this panel:

• Anchor ownership and rhythm. Give RevOps/Sales Ops the “hub” role, publish an operating calendar, and make decision rights explicit.

• Treat the plan like a product. Heavy upfront design, then ongoing tuning using real data: attainment curves, payout distributions, quota relief patterns, and SPIFF results.

• Listen to the field—and prove it. Use rep panels and focus groups, not just surveys, and show how their feedback shaped territories, quotas, policies, and edge-case rules (like mega deals and caps).

Do those things well, and sales comp planning stops being an annual source of anxiety—and becomes one of the most powerful levers you have for driving growth and cross-functional alignment.

To see how leaders at Stripe, ClickUp, BD, and Forma unpack these moves in their own words, check out the clips above or watch the full session with your GTM leadership team as a planning kickoff.