Program Manager, Toast

• This person must be comfortable building and leading working groups, influencing without authority, and operating effectively in a space where direction is not always clearly defined
• 3+ years of experience in program management, revenue strategy, sales operations, or go-to-market roles in product marketing
• Experience leading cross-functional initiatives in fast-paced, customer-facing environments
• Strong project management and organizational skills with the ability to manage multiple pilots simultaneously
• Experience communicating complex initiatives to executive stakeholders
• Strong analytical and problem-solving skills

Desirable

• The Program Manager - Sales Commercialization role is responsible for leading the strategy, development, and execution of Toast’s “pilot team.”
• This leader will own both the strategy of how Toast tests the sale of new products in the market but also how Toast drives new revenue growth with its testing strategy
• This role operates in a highly ambiguous, fast-moving environment with minimal predefined structure, requiring both strategic ownership and hands-on execution
• As the owner of innovation “cells,” this Program Manager is responsible for designing, running, and evolving product and go-to-market tests within Sales
• Working directly with a dedicated group of pilot Account Executives and a Sales Manager, this individual will lead a series of experiments on the company’s most promising new products
• They will define what to test, determine the appropriate strategies and tactics, and ensure each pilot is executed with rigor and clear learning objectives
• Beyond owning individual tests, this role also helps shape how the broader team operates—establishing processes, driving alignment, and continuously refining the testing approach
• Success in this role requires strong strategic instincts, the ability to translate ideas into actionable plans, and proven experience running complex, cross-functional programs
• Define pilot strategy, including mission, goals, success metrics, and alignment with company growth objectives
• Build and manage pilot roadmaps, timelines, milestones, and success criteria
• Identify key hypotheses, business questions, and performance thresholds for each initiative
• Lead cross-functional teams (Sales, Marketing, Product, Operations, Finance, Customer Success) and establish clear ownership and accountability
• Stand up pilot working groups, set meeting cadence, and ensure alignment across all stakeholders
• Partner with Sales to develop prospecting strategy, funnel tracking, and performance visibility
• Ensure pilots are properly resourced with tools, training, enablement materials, pricing, and operational workflows
• Monitor execution, track performance via dashboards, and ensure on-time delivery against goals
• Analyze results (conversion, adoption, retention, revenue impact) and translate insights into actionable recommendations
• Lead executive readouts and deliver clear, data-driven recommendations on scaling, iterating, or discontinuing pilots
• Build repeatable pilot playbooks, data strategies, and scalable processes
• Drive operational efficiency through tooling, AI, and optimized organizational structures