Senior Director of Sales Compensation Strategy, Planning and Operations

Toast

4h • $194,000 - $397,000 • Hybrid

About The Position

Toast is seeking a Senior Director of Sales Compensation Strategy, Planning and Operations to lead cross-functional partnerships that create motivating incentive plans and drive growth. The role requires a deep understanding of Toast’s Go-to-Market strategy and use of best practices to connect corporate strategy with sales behavior. It is a high-impact position partnering with senior leadership and contributing to long-term shareholder value.

The leader will oversee global sales compensation strategy and plan design, implementation, and ongoing improvement; maintain near- and long-term roadmaps and drive prioritization with the Steering Committee; analyze plan effectiveness and alignment with business goals and GTM metrics; and develop a high-performing compensation team. The position is part of Toast’s hybrid work model, with regional in-office expectations varying by location.

Requirements

• Bachelor's degree.
• 15 or more years of experience in commissions at a high-tech company; SaaS/Cloud experience is preferred.
• 8 or more years of experience managing a commissions/operations team in a fast-paced environment.
• Ability to influence cross-functionally across all levels of an organization.
• Experience analyzing sales commission processes and identifying automation opportunities.
• Comfort working in a fast-paced, dynamic, often ambiguous environment and meeting multiple deadlines.
• Effective project management skills; highly organized, independent, and self-motivated.
• Effective communication skills, including the ability to explain complex logic and scenarios clearly and simply to all levels of management.
• Track record of leading, growing, and developing high-performing teams.

Nice To Haves

• SaaS or FinTech industry experience.
• Strong experience with commission tools such as Xactly or Callidus, particularly configuration, plan design, and implementation.
• SaaS/Cloud company experience.

Responsibilities

• Develop and implement effective, motivating sales commission plans that connect corporate strategy with sales behavior, increase sales productivity, and drive revenue growth.
• Lead and coordinate global design, implementation, and continuous improvement of sales compensation plans.
• Own near-term and long-term Sales Compensation roadmaps and drive prioritization with the Steering Committee.
• Collaborate across organizational levels and functions to support sound decision-making and effective implementation.
• Analyze sales compensation plan effectiveness against business goals, strategy, performance metrics, and GTM goals.
• Lead and develop a high-performing team of compensation professionals.

Benefits

• Competitive compensation and benefits programs.
• Cash compensation, including overtime and bonus/commissions if eligible.
• Equity.
• Benefits intended to support a healthy lifestyle and flexibility for changing needs.

What This Job Offers

• Job Type: Full-time
• Career Level: Director