Title: Senior Product Manager, Support AI Experimentation 

Location: Remote, USA #remoteLI 

About Toast:

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love.

Are you bready* for a change? (Team Info)

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.

About this roll* (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.

Do you have the right ingredients*?

• 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.

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 https://careers.toasttab.com/toast-benefits.

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. At the center of this vision is Toast IQ: a single, unified assistant that orchestrates specialized agents across the Toast ecosystem. The Agent Platform makes this possible.

About the Role
As Principal Product Manager, Agent Platform you will define and scale the foundational platform that powers AI agents across Toast. This includes orchestration, tool integration, governance, evaluation, and observability. Your mission will be to make it easy for every product team at Toast to build, launch, and monitor high-quality AI agents  while ensuring Toast IQ delivers a seamless, consistent, and trustworthy experience. This is a deeply technical, high-leverage platform role with impact across all of Toast’s products. 

A day in the life (Responsibilities) 

• Define the long-term vision and roadmap for the Agent Platform, the shared orchestration and tooling layer for all Toast agents
• Build the platform capabilities that enable agent-to-agent collaboration, subagent routing (A2A), shared memory, and unified voice/tone
• Establish standards and systems for MCP tool development, entitlement controls, and tool orchestration
• Own evaluation, observability, and monitoring frameworks,  including instrumentation, tracing, eval pipelines, and production quality standards
• Enable teams across Toast to easily build and integrate agents
• Work with customers to understand AI quality
• Partner deeply with Engineering, AI/ML, design, and domain product teams to evolve platform capabilities as AI use cases expand

What you'll need to thrive (Requirements)

• 8+ years of product management experience, including significant ownership of technical platform or infrastructure products
• Deep familiarity with LLM systems, agent architectures, tool calling patterns, or AI evaluation frameworks
• Strong technical fluency: comfortable discussing APIs, orchestration layers, memory systems, protocols (e.g., A2A/MCP), and observability tooling
• Experience building developer-facing platforms or enablement systems used by multiple teams
• Proven ability to define, and own, quality standards and operationalize monitoring for complex systems in production
• Strong systems thinking and ability to balance short-term enablement with long-term architectural integrity
• Embrace and advocate for the use of AI tools to accelerate product discovery, streamline execution, and explore new product experiences - helping shape how we build and what we build.

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 https://careers.toasttab.com/toast-benefits.

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.

The first few weeks with Toast set the foundation for a restaurant’s long-term success. As Senior Product Manager, Onboarding you will help shape how thousands of restaurants successfully go live with Toast every year. Sitting at the intersection of product, operational processes, and the customer experience, you will identify the biggest friction points in onboarding and build intelligent, scalable solutions that help restaurants get live faster, reduce support burden, and ensure every customer starts their journey with confidence.

You will lead the development of intelligent onboarding capabilities that guide customers through setup, automate configuration where possible, and help teams proactively identify and resolve issues before they delay go-live. Your work will help Toast scale onboarding to every customer while maintaining a high-quality experience across segments, verticals, and geographies.

Your mission is to make it effortless for restaurants to get started with Toast — accelerating time-to-value, improving first-30-day satisfaction, and enabling Toast to scale as we grow.

This is a highly cross-functional role with impact across Toast’s products, internal teams, and customer journey.

A day in the life (Responsibilities) 

• Define the long-term vision and roadmap for Toast’s onboarding and activation platform, building the systems and experiences that help restaurants successfully get live and reach value faster
• Develop scalable onboarding capabilities across web and mobile that guide customers through setup, automate configuration where possible, and intelligently surface issues before they delay go-live
• Establish standards, frameworks, and product patterns that enable onboarding to operate as a platform across Toast products and teams
• Define and monitor key onboarding metrics and operational dashboards, using data to evaluate performance and drive improvements in key metrics
• Work closely with customers and internal operational teams to understand onboarding quality and identify opportunities to improve the customer experience
• Partner deeply with Engineering, AI/ML, Design, and domain product teams to evolve onboarding capabilities as Toast’s product ecosystem and AI-powered experiences expand

What you'll need to thrive (Requirements)

• 5+ years of product management experience, including ownership of complex customer-facing products or platforms
• Experience building products that improve customer onboarding, activation, or time-to-value
  
• Strong ability to identify friction across complex systems that span product experiences, operational processes, and customer journeys
  
• Proven ability to bridge product strategy with operational realities, turning manual processes or internal pain points into scalable product solutions
• Technical fluency and ability to collaborate effectively with engineering teams on systems that integrate across multiple products and services
• Experience using data and experimentation to drive measurable improvements in customer outcomes
• Demonstrated success leading cross-functional initiatives across product, engineering, design, and operational teams
• Strong systems thinking and ability to balance near-term impact with long-term scalable solutions
  
• Passion for improving customer experiences and delivering measurable business impact
• Embrace and advocate for the use of AI tools to accelerate product discovery, streamline execution, and explore new product experiences — helping shape how we build and what we build

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 https://careers.toasttab.com/toast-benefits.

#LI-REMOTE