Senior Automation Engineering Manager

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. As a Senior Engineering Manager focused on Automation Engineering, you will lead a team of Automation Engineers responsible for building and evolving automation platforms that enable Toast to deliver high-quality software at scale. You will define automation strategy, establish best practices, and deliver frameworks that empower product engineering teams to build and maintain their own automated tests. You will partner closely with Product Management and Engineering leaders across our Business Systems organization to prioritize high-impact automation initiatives, accelerate developer productivity, and reduce reliance on manual testing of happy-path scenarios. This role has broad technical and organizational influence and is a critical lever for improving delivery speed, confidence, and consistency across Toast. About this Role (Responsibilities) Lead and manage a team of Automation Engineers across multiple locations, providing technical mentorship, career development, and performance management. Own the automation engineering vision and roadmap, defining standards, patterns, and best practices aligned with Toast’s architecture and CI/CD pipelines. Design, scale, and maintain automation frameworks and platforms that are reliable, maintainable, and easy for engineering teams to adopt and extend. Enable engineering teams to own automation by providing strong frameworks, documentation, and tooling embedded into developer workflows. Partner with Product Management and Engineering leadership to prioritize automation investments based on business impact and delivery risk. Integrate automation deeply into the software development lifecycle, including CI/CD pipelines, build gates, and release processes. Define and track key automation metrics, including effectiveness, execution performance, flakiness, and impact on developer productivity. Provide hands-on technical leadership through architecture reviews, framework decisions, and code reviews as needed. Do You Have the Right Ingredients? (Requirements) 10+ years of experience leading and scaling automation engineering teams in a modern software engineering environment. Strong technical depth in automation engineering, including API, UI, and integration testing strategies. Hands-on experience with modern automation tools and frameworks such as Playwright, Cypress, Selenium, RestAssured, Postman/Newman, Karate, or similar. Proficiency in programming or scripting languages commonly used for automation, including Java, TypeScript/JavaScript, Python, or similar. Proven experience building shared automation platforms and frameworks adopted by multiple engineering teams. Experience integrating automation into CI/CD pipelines using tools such as GitHub Actions, Pipeline development for Jenkins, CircleCI, GitLab CI, and Git-based workflows. Experience defining automation metrics and using data to drive prioritization and improvement. Bachelor’s degree in Computer Science or equivalent practical experience. Special Sauce (Nice to Haves) Experience modernizing and scaling large automation codebases, including reducing technical debt and improving reliability and execution performance. Hands-on experience with test management and reporting ecosystems, such as TestRail or similar platforms, including building custom dashboards to communicate automation health and impact. Experience working with enterprise SaaS and business systems (e.g., Salesforce, NetSuite, Workday, or similar), including their APIs, complex data flows, and system integrations. Working knowledge of query languages such as SQL, SOQL, or similar, used for data validation and test verification. Experience with behavior-driven or specification-based testing approaches (e.g., Cucumber or similar) within shared automation frameworks. Strong expe ... (truncated, view full listing at source)