Principle, Sales Compensation Design

Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. We celebrate diversity and foster an inclusive environment, empowering employees to be their authentic selves.

About the Role

Five9 is looking for a Principal of Strategic Sales Compensation Design to design the incentive plans for our global sales organization—including Sales, Technical Sales, Partner Sales, and Business Development. This role will define how compensation design keeps pace with Five9’s shifting revenue model, where seat licensing increasingly carries bundled AI capacity, with incremental AI revenue arriving later through usage and expansion. The position involves close partnership with sales leaders, finance, and operations to build plan logic for a hybrid revenue model.

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.

Requirements

• 10+ years of experience in sales compensation design, sales strategy, revenue operations, or management consulting with an incentive design focus.
• 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.
• 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 (highly recommended).
• Experience supporting compensation governance in a public company environment and designing partner or channel compensation alongside direct sales plans (a plus).
• Excellent written and verbal communication skills.
• Bachelor’s degree in Business, Finance, Economics, or a related quantitative field, or equivalent experience.

Schedule

This role is hybrid, requiring 3 days a week (Tuesday, Wednesday, Thursday) in one of our offices: San Ramon, San Francisco, or Dallas.

Pay

The US base salary range for this role is $114,100—$355,100 USD. Actual compensation packages are based on factors unique to each candidate, including skill set, depth of experience, certifications, and specific work location. The total compensation package may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Benefits

• Health, dental, and vision coverage beginning on the first day of employment. Five9 covers 100% of the employee portion and shares a high portion of dependent costs.
• Short- and Long-Term Disability and Basic Life Insurance.
• 401k savings plan with employer matching.
• Access to an innovative mental health support platform offering personalized care, including therapy, coaching, and self-guided mindfulness exercises for covered employees and dependents.
• Generous Employee Stock Purchase Plan.
• Paid Time Off, company-paid holidays, paid volunteer hours, and 12 weeks of paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.