Principle, Sales Compensation Design

About the role

The role owns the end-to-end design of incentive plans for the global sales organization including Sales, Technical Sales, Partner Sales, and Business Development. You will partner closely with sales leaders, finance, and operations to translate business strategy into executable compensation frameworks. This position defines how compensation logic keeps pace with the shift from seat licensing to bundled AI capacity and usage-based revenue. You will own the incentive design calendar, plan documentation, and governance while ensuring alignment with revenue recognition and audit requirements. The position requires building quota methodologies that reconcile top-down and bottom-up targets across changing territories and headcount. You will also design territory and coverage models that balance revenue potential, account density, and rep capacity.

Key facts

What you'll do

Design and own the incentive plan calendar covering annual planning, in-year changes triggered by product launches, and new plan structures for new roles and routes to market.

Set pay mix, accelerator curves, thresholds, caps, and decelerators to drive the specific selling behaviors required by the business strategy.

Own plan documentation, governance processes, and version control while partnering with Finance on revenue recognition and audit compliance.

Build quota methodology that reconciles top-down and bottom-up targets and manages in-year reallocation as territories and market conditions evolve.

Design territory and coverage models that optimize revenue potential, account density, and rep capacity across global segments.

Model plan cost, expected attainment distribution, and cost of sales under multiple scenarios before plans are approved and launched.

Design compensation structures for Five9's hybrid revenue model where seat licensing carries bundled AI capacity and incremental AI revenue arrives later through usage and expansion.

Build incentive structures focused on expansion, renewal, and net revenue retention to complement new logo acquisition efforts.

Create SPIFs and sales contests tied to specific strategic priorities with clear cost ceilings and sunset dates to manage incentives effectively.

Benchmark Five9 plan design and pay levels against external market data and recommend adjustments to remain competitive.

Lead plan rollout communication to ensure sellers and managers understand exactly how the plan converts behavior into pay outcomes.

Analyze in-year plan performance data and recommend corrections when the plan is not producing the intended behavioral results.

Partner with Finance and Sales Operations to ensure compensation plans support accurate forecasting and financial reporting.

Champion the use of advanced financial modeling and attainment distribution analysis to test plan scenarios and forecast outcomes.

Communicate compensation design rationale to executive stakeholders and defend recommendations based on data and business impact.

Requirements

10+ years of experience in sales compensation design, sales strategy, revenue operations, or management consulting with an incentive design focus is required.

Demonstrated ownership of end-to-end incentive plan design from initial requirements through rollout and post-launch optimization.

Advanced financial modeling skills and fluency with attainment distribution analysis to forecast cost and performance under various scenarios.

Working knowledge of B2B SaaS go-to-market models, sales roles, and quota setting practices across multiple regions and segments.

Ability to present and defend design recommendations to sales and finance executives using clear narratives and data visualizations.

Understanding of regulatory and audit considerations related to compensation plan documentation and revenue recognition alignment.

Strong attention to detail ensuring plan logic, thresholds, and calculations are accurate across complex rule sets and version histories.

Collaboration mindset to work effectively with cross-functional stakeholders including Sales Leadership, Finance, Sales Operations, and Product.

Nice to have

Experience with cloud contact center or SaaS technology products is preferred to accelerate understanding of the business.

Background in organizations with hybrid revenue models combining subscription and usage-based components is preferred.

Familiarity with compensation systems such as spreadsheets, commission platforms, or incentive management tools is preferred.

Experience conducting compensation benchmarking against external market data to validate pay mix and levels.

Track record of managing sales compensation changes during in-year cycles without disrupting seller behavior.

Practical notes

This role is based in San Francisco, California, with a hybrid work arrangement.

Travel is not required for this position.

This position is eligible for standard employment authorization in the United States.

The compensation band listed is the maximum target base salary for this role.