Senior Product Manager, Toast
Support AI Experimentation
$125-254k
Salary partially dependent on location
Point of sale and management system for restaurants
Open for applications
Point of sale and management system for restaurants
1001+ employees
Open for applications
$125-254k
Salary partially dependent on location
1001+ employees
Company mission
Toast's mission is to enrich the food experience for all.
Role
Who you are
- 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
- 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
What the job involves
- 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?
- 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
Our take
Running a restaurant means managing a stressful set of elements, all needing to work together seamlessly to create a good experience for diners. Toast helps to streamline processes, and puts an end to piles of paperwork, by providing a platform whereby tableside ordering, menu modifications, labour management, payroll, and more are all housed in one system that can run from a tablet.
Toast offers restaurant-grade hardware and cloud-based, customisable payment solutions to serve clients from startup through to growth phase, as well as a service for established restaurants. By combining all the digital services a restaurant might need, the platform can act as the one and comprehensive solution for restaurants of any size, avoiding restaurateurs from having to invest in a range of technologies.
Toast has over 70,000 restaurants on its books, from food trucks to national brands, and its mobile ordering and payment solutions have made it a recognized brand for consumers. The company's IPO in 2021 saw it valued at over $30 billion and since then, it has added more features to its product suite including wholesale and catering order tools. Toast then, has proven its place as an indispensable player in the restaurant space.
Freddie
Company Specialist at Welcome to the Jungle
Insights
28% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Feb 2020
$400m
SERIES F
Apr 2019
$250m
SERIES E
Total funding: $899m
Company benefits
- Peer and company recognition programs
- Unlimited Vacation
- Sabbatical opportunity after five years
- Professional Development Reimbursement Program
- Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
- Various peer and company recognition programs
- 401(k) and matching
- Medical, Dental, & Vision Coverage
- Mental Health Benefits
- Subsidized backup childcare
Company HQ
Fort Point Channel Landmark District, Boston, MA
Leadership
Steve Fredette
(Co-Founder & President)They studied at MIT before co-founding Klick Mobile in 2009 and spending almost 7 years at Endeca. They left their Management role in June 2012 having co-founded Toast in May.
Aman Narang
(Co-Founder & CEO)Having studied Computer Science at MIT, they worked at Endeca for 5 years. They moved from working as Product Manager to work full-time as President of Toast in 2013, having co-founded it the previous year.
Jonathan Grimm
(Co-Founder & CTO)They also studied Computer Science at MIT before working as an Engineer for Endeca for over 4 years. They worked at Oracle for 5 months prior to co-founding Toast in May 2012.
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