Director, Sales Commercialization

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. The Director, Sales Commercialization plays a dual role as operator and architect of Toast’s market-facing innovation engine. You will lead a pilot sales team that tests new products, pricing, and revenue levers in the market—rapidly validating ideas and unlocking scalable growth. You will also build and own the infrastructure behind this work, partnering cross-functionally to define how opportunities are selected, prioritized, and tested—establishing the systems and governance that power a high-velocity portfolio of innovation and GTM strategies. Operating at the intersection of Sales, Product, Marketing, you ensure resources are focused on the highest-impact opportunities—turning strong hypotheses into scaled revenue. A day in the life (Responsibilities) Mission Roadmapping: Evolve the team’s mission and org design to maximize revenue levers, coordinating planning and resourcing to scale with Toast’s growth. Commercialization Strategy: Architect the long-term vision for product validation, aligning the testing roadmap with growth targets to fuel the core PL. Scalable Playbooks: Standardize frameworks, systems, and tools to build a world-class "Center of Excellence" for consistent, repeatable experimentation. Executive Decision-Making: Drive high-stakes decisions by delivering high-impact readouts and managing the decision engine for the SLT and GTM leaders. Experimentation Governance: Establish rigorous decision frameworks, stage-gates, and escalation paths to manage risk and ensure objective pilot evaluation. Data Strategy: Define and own the metrics and tracking systems that turn pilot data into actionable insights for executive decision-making. People Leadership: Recruit and develop a high-performing team of sales and ops professionals, fostering a "fail fast, learn faster" culture. Strategic Influence: Serve as a core GTM leader, translating field insights into long-term strategic investments for the multi-year roadmap. What you'll need to thrive (Requirements) Bachelor’s degree in Business, Marketing, Operations, or related field (or equivalent experience) 5+ years of experience in program management, revenue strategy, sales operations, or go-to-market leadership Proven experience owning and operating multiple concurrent initiatives or programs at scale Demonstrated ability to influence senior stakeholders and drive decisions at the executive level Strong ability to navigate ambiguity, create clarity, and put a stake in the ground despite barriers What will help you stand out (Nonessential Skills/Nice to Haves) Experience in SaaS, restaurant technology, or hospitality Familiarity with POS systems, online ordering, or restaurant operations Background in building or scaling experimentation, incubation, or innovation programs Experience with revenue analytics, forecasting, and performance dashboards Program management or agile certifications (e.g., PMP, Agile) 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’ ch ... (truncated, view full listing at source)