Senior Product Manager, Support AI Experimentation

Toast

4d • Remote

About The Position

The Support R&D team is shaping how hundreds of thousands of restaurants get help — and how Toast's care organization delivers it. Our scope spans three interconnected domains: the self-serve experiences customers use to understand their accounts, find answers, and resolve issues independently; the tools that empower Toast's human care agents to deliver fast, accurate, high-quality support via phone, chat, and email; and the AI-powered systems that deliver support directly — through chat and voice — at scale. This is a high-leverage, high-visibility domain at the intersection of product, support operations, and AI. The systems we build connect deep customer context — accounts, devices, subscriptions, billing, cases — with intelligent knowledge retrieval, omnichannel support infrastructure, and increasingly capable AI. Our work directly influences deflection rates, resolution speed, customer effort, and the overall quality of the Toast support experience. As our Senior Product Manager, Support AI Experimentation, you sit at the front edge of that work — operating as our dedicated scout and experimentation lead for AI-driven support concepts. While partner teams own the infrastructure and scale-out, you own the question that comes before all of that: what should we actually try? This role is for someone who can't stop thinking about what's next in AI, who has strong opinions about what's hype versus signal, and who gets genuine energy from turning a "what if" into a fast, scrappy experiment with a clear answer.

Requirements

• You are genuinely AI-native: you follow model releases, you experiment with new tools on your own time, you have real opinions about what's useful versus overhyped, and you get excited when someone says "have you seen what this new model can do?" — this is not optional, it is the core of the role.
• 5+ years of product management experience, with meaningful time spent on AI or ML-powered products in production; bonus if that includes conversational AI, support tooling, or customer-facing automation.
• Demonstrated ability to run fast, scrappy experiments — you know how to get to a meaningful result without waiting for perfect infrastructure, and you know how to read the signal clearly when you get there.
• Strong judgment about which ideas are worth pursuing: you can articulate why a particular AI approach is worth Toast's time, and you can say no (and explain why) just as confidently as you say yes.
• Comfortable operating in ambiguity with a shifting portfolio — you don't need a stable roadmap handed to you, and you thrive when the work evolves quickly as the technology does.
• Able to connect experimental work to business outcomes and communicate findings credibly to technical and non-technical stakeholders, from engineering partners to support operations leadership.
• Experience working across team boundaries to hand off proven concepts — you know how to set a partner team up for success and don't need to own the build to feel ownership over the outcome.

Nice To Haves

• bonus if that includes conversational AI, support tooling, or customer-facing automation.

Responsibilities

• Scout the AI landscape continuously — new models, tools, agents, retrieval approaches, voice systems — and rapidly develop sharp POVs on what Toast's support organization should be testing and why.
• Design and run lightweight experiments to pressure-test AI-driven support concepts before they're ready for infrastructure investment, moving from hypothesis to results without waiting for perfect conditions.
• Make go/no-go calls on exploration threads with clarity and conviction, synthesizing experimental findings into crisp recommendations that partner teams can act on.
• Own and actively manage a shifting experimentation roadmap, knowing when to pursue a new thread, when to double down on early signal, and when to kill something that isn't working.
• Translate findings into business-relevant outcomes — connecting experiment results to deflection rates, resolution speed, customer effort, and care team efficiency — so stakeholders understand what's at stake.
• Collaborate closely with engineering, data science, support operations, and platform teams to hand off proven concepts and ensure experimentation outputs land in production.

Benefits

• competitive compensation and benefits programs
• great earnings potential
• means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs
• cash compensation (overtime, bonus/commissions if eligible)
• equity
• benefits

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed