Principle, Sales Compensation Design

Five9

San Francisco (CA)

Hybrid

USD 114,000 - 355,000

Full time

12 days ago

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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.

Skills

Sales compensation design

Sales strategy

Revenue operations

Management consulting

Incentive design

AI tools for scenario modeling

Education

Bachelor’s degree in Business, Finance, Economics, or related quantitative field

Tools

Incentive compensation platforms

AI tools for scenario modeling

Job description

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 required

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our San Ramon office is required.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

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. We also offer 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

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.

The US base salary range for this role is below.

$114,100—$355,100 USD

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our San Francisco office is required.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

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. We also offer 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

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.

The US base salary range for this role is below.

$114,100—$355,100 USD

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our Dallas office is required.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

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. We also offer 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

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.

The US base salary range for this role is below.

$114,100—$355,100 USD

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer.

View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

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