Senior Product Manager, Payroll Onboarding

Toast

1d•Hybrid

About The Position

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 Payroll team is part of Toast Team Suite — our all-in-one, AI-powered platform for managing restaurant teams. Our mission is to make paying and managing employees effortless, accurate, and reliable. We operate in a tight Product–Design–Engineering triad with a high bar for ownership, pace, and outcomes. We value learning velocity, strong product craft, and measurable impact. At Toast, the first 90 days determine everything: whether a customer successfully runs payroll, how much they rely on support, and ultimately whether they stay and grow with us. When onboarding works, customers gain confidence fast. When it doesn’t, issues compound — errors, care tickets, and churn. This role owns that outcome. As the Product Manager leading Payroll Onboarding, you’ll define and deliver the experience that gets every customer from contract signature to first successful payroll — quickly, accurately, and with confidence. This is one of the highest-leverage surfaces in the business, with direct impact on activation, pNPS, support costs, and retention. The problem space is well understood and already in motion. The opportunity now is to translate that clarity into measurable results — and to reimagine onboarding as an intelligent, system-driven experience powered by AI. More broadly, this role sits at the center of a critical company challenge: orchestrating accurate, low-friction onboarding across a multi-product ecosystem. Getting this right is foundational to customer trust and a key driver of Toast’s long-term growth. We’re looking for a Senior Product Manager to lead the next evolution of Payroll onboarding — making it faster, more intelligent, and fundamentally more reliable. You’ll own the onboarding system end-to-end: the customer-facing experience, the internal tools that power implementation, and the workflows that connect product, services, and operations.

Requirements

6–8+ years of product management experience, with a demonstrated track record of owning and driving meaningful business outcomes in complex, high-impact product areas
Strong ownership of metrics and business outcomes. Experience defining, instrumenting, and improving key metrics — and communicating progress and tradeoffs to senior stakeholders
Experience with onboarding or activation-heavy products. Deep understanding of how customers reach first value — and how onboarding impacts retention and support
CX mindset (bonus, not required). Experience shaping end-to-end onboarding journeys across product and human-assisted touchpoints
AI fluency. Comfortable using AI in day-to-day product work (prototyping, analysis, iteration), with a point of view on how AI and agentic systems can reshape product and operations
Strong product and data judgment. Ability to synthesize qualitative and quantitative inputs into clear decisions and priorities
Clear, effective communicator. Able to distill complexity into crisp narratives and influence cross-functional and executive audiences
High ownership and comfort with ambiguity. You create clarity, drive progress, and take responsibility for outcomes in complex, evolving spaces
Strong cross-functional leadership. Proven ability to align Engineering, Design, Services, and GTM partners around shared goals

Nice To Haves

CX mindset (bonus, not required). Experience shaping end-to-end onboarding journeys across product and human-assisted touchpoints

Responsibilities

Set the onboarding strategy and roadmap. Define a clear, outcome-driven vision that improves activation, reduces friction, and builds lasting customer trust
Own and drive core business metrics. Instrument, monitor, and improve key metrics including pNPS, activation rate, time-to-first-payroll, care ticket volume, and early retention.
Represent performance in leadership forums — diagnosing gaps, driving accountability, and aligning teams on action
Reimagine onboarding through an AI-first lens. Deliver intelligent automation, guided configuration, and proactive error prevention. Use AI not just in the product, but in how you prototype, validate, and accelerate development
Evolve onboarding into an AI-augmented system. Partner with services teams to redesign workflows using AI-assisted tools and emerging agentic patterns to improve speed, accuracy, and scalability
Drive a cohesive, end-to-end onboarding experience (CX). Ensure alignment across product UX, human-assisted onboarding, and cross-product configuration — creating a seamless path to first value
Develop deep customer and operational insight. Leverage interviews, onboarding sessions, care data, and behavioral analytics to identify root causes and prioritize effectively
Lead execution with clarity and quality. Partner closely with Design and Engineering to deliver high-quality, high-impact product experiences
Contribute to a high-performance team. Build strong cross-functional relationships and raise the bar on ownership, collaboration, and outcomes