Principal Design Operations Program Manager, AI - Remote

Overview

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.

In Short

• Own the AI ways of working roadmap for Design.
• Build cross-functional AI workflows with PM Ops and Eng Ops.
• Instrument and track progress.
• Evaluate, pilot, and operationalize AI tooling for Design.
• Create scalable enablement resources.

Requirements

• 6+ years of experience in design operations, program management, or a systems-focused operations role.
• A design ops or systems thinking foundation.
• Genuine technical fluency.
• Proven experience driving behavior change.
• Strong analytical and pattern-recognition skills.
• A rigorous, current point of view on AI.

Benefits

• Competitive compensation and benefits programs.
• Flexible total rewards package.
• Opportunities for professional growth.
• Inclusive and diverse work environment.
• Access to cutting-edge AI tools.