Senior Director of Sales Compensation Strategy, Planning and Operations
Remote · 8+ years experience · Remote · Posted Oct 19, 2026
At a glance
- Experience
- 8+ years experience
- Workplace
- Remote
- Location
- Remote
About the role
- We're seeking a Senior Director of Sales Compensation Strategy, Planning and Operations to lead cross-functional partnerships that create motivating incentive plans and drive growth.
- This leader will maintain a deep understanding of Toast's Go-to-Market strategy and leverage best practices to link corporate strategy with sales behavior.
- This is a high-impact role that will partner across our senior leadership team with the opportunity to drive long-term shareholder value.
Responsibilities
- Develop & implement effective and motivating sales commission plans that link corporate strategy with sales behavior, increase sales productivity and drive revenue growth
- Lead & coordinate global efforts for the design, implementation, and continuous improvement of sales compensation plans
- Own both near-term & long-term Sales Compensation roadmaps and drive prioritization with the Steering Committee
- Collaborate across all levels of the organization via cross-functional relationships to ensure sound decision-making and effective implementation
- Continuously analyze sales compensation plan effectiveness in achieving business goals/strategy and performance metrics to ensure alignment with GTM goals
- Lead and develop a team of high-performing compensation professionals
Requirements
- Bachelor's degree
- 15+ years of high-tech company experience (SaaS/Cloud model preferred) in commissions
- 8+ years of experience managing a commissions/operations team in a fast-paced environment
- Ability to influence cross functionally across all levels of the organization
- Experience in analyzing sales commission processes and finding automation opportunities
- Comfortable in a fast-paced, dynamic & often ambiguous environment, with the ability to meet multiple deadlines
- Effective project management; highly organized, independent, and self-motivated
- Effective communicator who can take complex logic and scenarios and describe them simply and clearly to all levels of management
- Track record of leading, growing, and developing high-performing teams
Preferred qualifications
- SaaS or FinTech industry experience
- Strong experience with commission tools (Xactly, Callidus, etc.) with a focus on configuration, plan designs and implementation
Workplace
- Remote role in the USA
- Embraces a hybrid work model that fosters in-person collaboration while valuing individual needs
Skills
- Xactly
- Callidus
