In a project-based company, salespeople are heroes for closing large, complex, custom projects. This incentive structure is directly opposed to a product model that requires standardization. The transition to product will fail unless sales compensation and culture are realigned to favor standard product sales.

Assigning expansion quotas to Customer Success (CS) is a critical mistake. CS should focus on implementation, adoption, and value realization, creating the conditions for growth. However, the act of selling the expansion is a core sales responsibility that requires a sales skillset and incentive structure.

Delaying compensation plans until after the fiscal year begins creates a vacuum where salespeople are unsure how to behave. This uncertainty paralyzes productivity and demotivates the team, wasting the energy generated by the sales kickoff (SKO).

A one-size-fits-all sales role fails in consumption models. Success requires segmenting the team into specialized roles—new business acquisition, customer onboarding, and account management—each with distinct incentives aligned to their specific function, from initial sign-up to value realization and expansion.

Founders and CEOs can develop an inflated sense of their contribution by focusing only on the final executive meeting. They often overlook the months of prospecting, relationship-building, and deal choreography done by the sales rep, leading to unfair perceptions about who truly 'closed the deal.'

Don't finalize a comp plan in an executive silo. Share the draft with trusted, top-performing reps and ask them to break it. They will immediately spot loopholes and unintended incentives, allowing you to create a more robust plan that drives the right behaviors from day one.

A common OKR failure is assigning teams high-level business metrics (like ARR) which they can only contribute to, not directly influence. Success requires focusing on influenceable customer behaviors while demonstrating how they correlate to the company's broader contribution-level goals.

Annual plans can't predict every business need, like a new product launch or acquisition. A pre-approved budget for discretionary incentives (SPIFs) allows sales leaders to quickly motivate reps toward new, unforeseen priorities without having to disrupt the core compensation plan mid-year.

Sales compensation is the most powerful lever for changing a sales team's behavior quickly. More than training or directives, incentives tell reps what they are supposed to do and why, directly shaping their daily actions and strategic focus.