Principle, Sales Compensation Design

Five9 is looking for a Principle of Strategic Sales Compensation Design to design the incentive plans for our global sales organization – Sales, Technical Sales, Partner Sales and Business Development. Close partnership with sales leaders, finance and operations will round out the scope of this position.

Five9’s own revenue model is shifting: seat licensing increasingly carries bundled AI capacity, with incremental AI revenue arriving later through usage and expansion. This role will define how compensation design keeps pace with that shift — building the plan logic for a hybrid revenue model that most legacy comp frameworks were never built to handle.

Incentive Plan Design & Governance

• Own the incentive design calendar — including the annual plan cycle, in-year plan changes triggered by product launches or go-to-market shifts, and new plan structures for new roles, segments, and routes to market.
• Set pay mix, accelerator curves, thresholds, caps, and decelerators — to drive the selling behavior the business needs.
• Own plan documentation, governance, and version control — partnering with Finance on revenue recognition and audit requirements.

Quota, Territory & Plan Economics

• Build quota methodology that reconciles top-down and bottom-up targets — running in-year reallocation as territories, headcount, and market conditions move.
• Design territory and coverage models — balancing revenue potential, account density, and rep capacity.
• Model plan cost, expected attainment distribution, and cost of sales — under multiple scenarios before plans are approved.

Retention, Expansion & Hybrid Revenue Design

• Design compensation 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 for expansion, renewal, and net revenue retention — alongside new logo acquisition.
• Design SPIFs and sales contests tied to specific strategic priorities — with clear cost ceilings and sunset dates.

Benchmarking, Rollout & Performance Management

• Benchmark Five9 plan design and pay levels — against external market data, and recommend adjustments.
• Lead plan rollout communication — so sellers and managers understand exactly how the plan converts behavior into pay.
• Analyze in-year plan performance — and recommend corrections when the plan is not producing intended behavior.

Candidate Requirements and Experience

• 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 incentive plan design.
• Advanced financial modeling skills and fluency with attainment distribution analysis.
• Working knowledge of B2B SaaS go-to-market models and sales roles.
• Ability to present and defend design recommendations to sales and finance executives.
• Experience designing compensation for hybrid revenue models that combine subscription or seat licensing with usage and consumption components, familiarity with incentive compensation platforms.
• Hands-on proficiency with AI tools, and a point of view on how they can sharpen scenario modeling and quota design, is highly recommended. Experience supporting compensation governance in a public company environment and designing partner or channel compensation alongside direct sales plans is a plus.
• Excellent written and verbal communication skills.
• Bachelor’s degree in Business, Finance, Economics, or a related quantitative field, or equivalent experience, is required.

Benefits

• Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost. Five9 also offers Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
• Access to an innovative mental health support platform that offers personalized care and resources in areas such as therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
• Generous employee stock purchase plan.
• Paid Time Off, company-paid holidays, paid volunteer hours, and 12 weeks paid parental leave.