Principal Design Operations Program Manager, AI

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. We are seeking a Principal Design Operations Program Manager to own AI-enabled ways of working for Toast's design function. This role sits inside the Design Operations team while operating as Toast's dedicated Design lead within a cross-functional AI Productivity triad alongside PM Ops and Engineering Ops. Designers across Toast are already using AI. The prototypes are coming faster, the tools are multiplying, and the experimentation is underway. What's missing is the layer above it: a shared model for what excellent AI-augmented design practice actually looks like, and the systems to make it stick across a distributed team. The work spans behavioral change, tooling strategy, cross-triad workflow design, and instrumentation, all in service of helping a large, distributed design organization make an intentional, durable shift to AI-native ways of working. This is a high-visibility, high-stakes role for someone who's rigorous about AI: someone who can separate signal from noise, look at where designers are actually spending their time today, identify the real friction points, and build the systems and frameworks to close the gap, while staying on top of where AI capabilities are evolving and what that means for how design teams should operate next. A day in the life (Responsibilities) Own the AI ways of working roadmap for Design. Define and drive a prioritized set of investments for how designers integrate AI into core workflows (from problem framing to prototyping to delivery), ensuring the team is making intentional, scalable shifts and not just layering tools on top of existing habits. Build cross-functional AI workflows with PM Ops and Eng Ops. Partner across the triad to identify and remove handoff friction, and build shared workflows that enable designers, PMs, and engineers to work together in new ways. Instrument and track progress. Build toward a clear picture of where the design team is on their AI journey (tool usage, workflow shifts, time to value) and use that data to drive decisions and demonstrate impact. Evaluate, pilot, and operationalize AI tooling for Design. Manage the design team's AI tooling landscape: assess emerging tools (prototyping, workflow automation, design-to-code), run structured pilots, and lead rollouts in partnership with AI Foundations. Maintain a current, rigorous point of view on where AI is headed and what it changes for design practice. Create scalable enablement resources. Build the guides, playbooks, and community infrastructure that help the team adopt new ways of working confidently and without constant hand-holding. What you'll need to thrive (Requirements) 6+ years of experience in design operations, program management, or a systems-focused operations role, with demonstrated impact at scale in a fast-moving org. A design ops or systems thinking foundation. You understand how design organizations function, where they get stuck, and how to build systems people actually adopt. Genuine technical fluency. You don't need to be an engineer, but you understand how AI tools work, can evaluate technical trade-offs, and can work closely with engineers on cross-functional workflows. You've personally used AI-assisted tools in substantive ways and can speak credibly about how they change the work. Proven experience driving behavior change. You've led large-scale change management efforts before. You know the difference between a communication moment and a reinforcement mechanism, and you build the latter. Strong analytical and pattern-recognition skills. You synthesize signals across a distributed org, identify root causes, and build frameworks that address them systematically rather than symptomatically. A rigorous, current point of view on AI. You're not just aware of the latest tools. You have ... (truncated, view full listing at source)