Dear Calcy: When Incentive Planning Gets Left Behind

Dear Calcy,

Every year we go through multiple rounds of sales planning — capacity models, quotas, headcount, coverage — only to realize that no one really talked about incentives until the very end. By the time comp comes up, it’s too late to course-correct. The plans don’t reflect what we actually want reps to prioritize, and we’re stuck trying to bolt incentives onto a strategy they weren’t part of. How do we change that?

Sincerely,
Left Out of the Loop

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Dear Left Out of the Loop,

You’ve pinpointed one of the biggest (and most costly) gaps in sales planning: treating incentive design like an afterthought. When compensation isn’t part of the initial strategy conversations, the result is often a set of mismatched plans — where behaviors, goals, and payouts are pointing in different directions.

The good news? This is fixable. But it takes intention and cross-functional commitment.

Here’s how to bring incentives into the planning conversation — right when they belong:

1. Make Incentives a First-Class Input, Not a Final Step

Incentive planning isn’t something you “do after” quotas and territories — it’s something that should shape them. As soon as you’re modeling headcount and coverage, start asking: What behaviors do we need to drive? What levers are available? What trade-offs are we willing to make?

2. Create a Shared Planning Milestone Map

The easiest way to get misaligned? Work off different timelines. Align Sales, Finance, RevOps, and HR on when key decisions need to happen — and when incentive implications should be reviewed. When comp owners have a seat at the table from day one, they can raise flags before things go off-course.

3. Design for Agility, Not Just Accuracy

It’s tempting to focus only on plan mechanics and payout precision. But in a volatile market, flexibility matters more. Build plan structures that can evolve without requiring a total overhaul — think adjustable weightings, dynamic SPIFs, or tiered accelerators that respond to shifting priorities.

4. Pressure-Test for Alignment, Not Just Math

Before rollout, do a reality check: Are the behaviors we’re paying for the same ones the business needs right now? Are comp levers reinforcing or contradicting strategic bets? When incentive plans match intent, reps focus faster — and outcomes follow.

Compensation isn’t just a reward mechanism. It’s a strategic signal. When it’s misaligned, execution suffers. When it’s part of the planning process from the start, it becomes one of your sharpest tools for change.

Here’s to planning smarter, aligning earlier, and ensuring incentives work as intended!

– Calcy