Strategic Sales Compensation Architect

Five9

San Francisco (CA)

Hybrid

USD 114,000 - 355,000

Full time

14 days+

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Benefits offered by this job

Health, dental, and vision coverage

401k with employer matching

Employee stock purchase plan

Paid Time Off and holidays

Job summary

Five9 is seeking a senior leader to design strategic sales compensation for its global, hybrid revenue model. You will own the incentive design calendar, determine pay mix, and govern plan documentation while partnering with sales, finance, and operations.

The role requires 10+ years in sales compensation design, strong financial modeling, and knowledge of B2B SaaS go-to-market models. The position is hybrid, with in-office days in San Ramon/San Francisco areas and broad responsibilities across

Qualifications

10+ years of experience in sales compensation design, sales strategy, revenue operations, or management consulting with an incentive design focus.
Proven 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 combining subscription or seat licensing with usage components; familiarity with incentive compensation platforms.

Responsibilities

Own the incentive design calendar — annual plan cycle, in-year changes, and new structures for roles, segments, and routes to market.
Set pay mix, accelerator curves, thresholds, caps, and decelerators to drive required selling behavior.
Own plan documentation, governance, and version control with Finance on revenue recognition and audits.
Build quota methodology and in-year reallocation as territories and conditions move.
Design territory and coverage models balancing revenue potential, account density, and rep capacity.
Model plan cost, attainment distribution, and costs of sales under multiple scenarios before approvals.
Design compensation for Five9’s hybrid revenue model with bundled AI capacity and later usage/expansion revenue.
Build incentive structures for expansion, renewal, and net revenue retention alongside new logo acquisition.
Design SPIFs and sales contests with clear cost ceilings and sunset dates.
Benchmark plan design against external market data and lead rollout communications; analyze in-year performance and adjust as needed.