Principle, Sales Compensation Design

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. 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. Key Responsibilities 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 req…