Principal Design Operations Program Manager, AI

Toast

1d • Remote

About The Position

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.

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 a considered, evolving perspective on how AI is reshaping product development roles and design practice specifically.

Nice To Haves

• You've worked across more than one function's ops (PM ops, eng ops, design ops) and understand how the full product development triad operates, not just one function's slice of it.
• You have a background in UX research or design practice and bring first-hand understanding of what designers and researchers actually need to do their best work.
• You've built infrastructure for others to experiment: internal tooling, self-serve resources, and sanctioned pathways that keep security and quality intact while teams move fast.
• You have a genuine, considered point of view on what the designer's role looks like in two years, and you're already thinking about how to prepare people for it.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees