Principal Design Operations Program Manager, AI at Toast

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 a considered, evolving perspective on how AI is reshaping product development roles and design practice specifically. About You You are a dynamic leader with proven impact in previous roles who is ready and willing to take on new challenges! You’re excited to join the remotely distributed group of product designers, user researchers, design ops leaders, and product managers that compose the Toast Design team. You embody the tenets that drive Toast’s Design practice: • You have a founder’s mentality: and exhibit ownership of outcomes over outputs. You own the quality and outcomes associated with full end to end experiences. • You lift others up: and recognize you don’t have to be a manager to engage and exhibit true leadership. You find formal ways to utilize your personal skill set to uplevel those around you. • You drive action through influence: and appreciate that building trusting and productive relationships with those around you is integral to driving action. You build strong relationships to enact influence throughout the entirety of the area of the business you work within. • You build strong perspectives: and guide yourself and your teams to make good decisions quickly and often. You collaboratively make well informed decisions with large scale impact across the area of the business you work within. • You raise the bar: and commit to continually improving the technical skills relevant to your role. You find large scale, creative methods to continually build your skill set. AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at [Upgrade to PRO to see link] #LI-Remote The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible). Pay Range$165,000—$264,000 USDHow Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: [Upgrade to PRO to see link] Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [Upgrade to PRO to see contact]. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.