Senior Director of Sales Compensation Strategy, Planning and Operations

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Toast is driven by building the platform that helps restaurants and businesses adapt, take control, and get back to what they do best: building the businesses they love. Role Description 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. A day in the life (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 What you'll need to thrive (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 Special sauce* - SaaS or FinTech industry experience - Strong experience with commission tools (Xactly, Callidus, etc.) with a focus on configuration, plan designs and implementation AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits. The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Zone A $248,000-$397,000 USD Zone B $215,000-$344,000 USD Zone C $194,000-$310,000 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast People Are the Secret Ingredient in Our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.