A rep closes a logo in month eleven that churns in month fourteen. The commission already paid out. The board finds out about the churn a quarter later, in a different meeting, presented by a different team, with no line connecting it back to the deal that caused it. Nobody in the room made a bad decision. The comp plan just never asked the question that mattered.

Most sales compensation is built around one event: closed-won. It's clean, it's measurable the day it happens, and it's easy to explain to a new hire in their first week. The problem is that closed-won is a proxy for the thing you actually want, which is durable revenue, and proxies drift from the thing they're standing in for the moment people start optimizing against them directly. The gap between the proxy and the real target doesn't show up immediately — it shows up on a lag long enough that nobody connects the two events when it finally does.

What the comp plan actually teaches reps

A rep learns the real rules of the job from what gets paid, not from what gets said in the kickoff deck. If the plan pays full commission on any signed logo regardless of fit, reps will chase logos regardless of fit — not because they're gaming the system, but because that's the rational response to the incentive in front of them. The mismatch between the pitch and the deal happens quietly, deal by deal, and it never shows up as a single bad decision. It shows up eighteen months later as a churn number nobody can trace back to its source.

The accounts that were never going to be happy customers still count as wins the day they sign. That's the whole design flaw in one sentence. And it compounds: a rep who closes five logos that never should have closed still ranks above a rep who closed three logos that all renewed, at least until the retention numbers catch up — which by then is someone else's quarter to explain.

Why NRR rarely makes it into the plan

Most GTM leaders will tell you NRR is the metric that matters. Almost none of them pay commission on it. The reasons are practical, not philosophical: NRR lags the deal by a year or more, it's harder to attribute to one rep when a customer success team is also touching the account, and clawing back commission on a churned deal is an uncomfortable conversation nobody wants to have twice a quarter. So the plan defaults to what's clean and immediate, even when everyone privately knows it's rewarding the wrong behavior.

The fix isn't necessarily paying full commission on retention — that introduces its own distortions, since a rep has limited control over a customer's experience eighteen months out, long after onboarding, support, and product decisions the rep never touched have shaped the outcome. It's building in a smaller, deliberate counterweight: a clawback on early churn, a bonus multiplier tied to a cohort's first-year retention, something that makes the rep's incentive brush up against the business's actual interest instead of running parallel to it forever. Even a modest counterweight changes behavior, because reps are unusually good at reading exactly what a comp plan rewards down to the decimal point.

The quiet cost of getting this wrong

Nobody budgets for the cost of a comp plan that's misaligned with retention, because it doesn't show up as a line item. It shows up as CS teams inheriting accounts that were never going to renew, as a rep roster that looks productive on bookings and mysteriously thin on repeat business, and as a board deck where the growth story and the retention story are quietly telling two different tales about the same sales org. It also shows up as CS burnout — a team spending its energy trying to save accounts that were never a fit, instead of expanding accounts that were.

Getting the incentive design right doesn't fix everything downstream of it, but it changes what a rep is rewarded for noticing in the first place — including which accounts were worth the outreach to begin with. That's also where the front end of the funnel matters more than most comp conversations give it credit for: a rep spending their best hours on outbound built around genuine fit, instead of volume for its own sake, is easier to compensate honestly, because the deals reaching the pipeline were closer to the right ones from the start. Skyp's per-contact personalization is built around exactly that — targeting and messaging tuned to real fit signals, not blast volume — so the pipeline a comp plan ends up rewarding was closer to durable in the first place.