About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

By the Numbers:

Named #1 best software for small business of 2024 by G2
2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing
Over $500M in annual revenue
The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs

There are 6.2M employers in the US, 98% have fewer than 100 employees ⁽¹⁾
550,000 new businesses are created each year in the US⁽¹⁾

What Product Management is like at Gusto:

Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing.
We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Role:

At Gusto, we're building a world where every customer need is understood, matched with the right expertise, and driven to the right resolution, by the right person or AI, at the right time. Making that real requires a sophisticated "System of Intelligence" that understands customer intent, judges problem complexity, decides whether AI or a human should take it, and retrieves exactly the right knowledge and data to answer. T

As Principal Product Manager for the AI-First Service Platform, you'll own core capabilities of the intelligence layer and surface area experience behind Gusto's customer-facing AI help/service — the models and infrastructure that determine what a customer needs, whether AI or a human should resolve it, what context travels with every handoff, and what knowledge the system draws on to answer. You'll own multiple capabilities and/or channels across voice, chat, and email, and you'll be accountable for how well the whole parts of the system actually perform for customers, not just what ships.

This is a role for a systems thinker and hands-on builder. You'll tear down what's overly complex, design simple and durable architecture in its place, experiment and iterate rapidly and create the conditions where operational efficiency and great customer experience reinforce each other — not trade off against each other.

We're looking for someone who can think from first principles, influence at the senior level, and still get into the details when it matters.

About the Team:

The Unified Service Platform (USP) team is the operational backbone behind Gusto's customer experience. We build intelligent systems that align Sales and Service teams around a single source of truth — replacing fragmented tools with a cohesive "System of Intelligence" that gives every team member the full context they need to serve customers effectively.

We are an AI-native team building agentic solutions that transform how work gets done. We own the AI-Human-AI loop across voice, chat, and email — ensuring every interaction, internal or external, is seamless, informed, and effortless. Our north star is simple: make it easy for Gusto's teams to do their best work, so every business we serve feels the difference.

Here’s what you’ll do day-to-day:

Own core capabilities of Gusto's AI service intelligence layer (e.g. intent understanding, escalation and handoff decisions, context ingestion, or knowledge and retrieval) across voice, chat, and/or email
Build and refine the models and frameworks that decode what customers need and determine whether AI or a human is the right path to resolution, partnering with engineering and data science to continuously improve accuracy and eliminate context loss across handoffs
Own the evaluation layer for the systems you ship — define what "good" means, build the evals and monitoring that prove it in production, and close the loop between what the model does and what the customer actually experiences.
Experiment, learn, iterate, and ship impactful solutions rapidly.
Identify and dismantle legacy systems and hard-coded workflows that create friction, replacing them with flexible, intelligent architecture that scales with Gusto's growth
Collaborate with GTM and Service teams so the system reflects real operational needs, translating frontline insights into prioritized product decisions
Define and track the metrics that matter — solve rate, satisfaction, escalation accuracy, handle time, and customer effort — using data to diagnose breakdowns in the customer journey and drive continuous improvement

Here’s what we're looking for:

A systems thinker with 8+ years of product management experience building complex, data-intensive platforms — ideally in customer service, CRM, or enterprise SaaS environments where routing, orchestration, or workflow automation were core to the product
Deep familiarity with AI/ML concepts — particularly intent classification, NLP, and agentic systems — with a track record of translating model capabilities into tangible product outcomes at scale
A hands-on builder who can move fluidly between strategy and execution — equally comfortable whiteboarding architecture with engineers, influencing senior stakeholders, and diving into the data to pressure-test assumptions
Strong cross-functional instincts and a demonstrated ability to align Sales, Service, and Engineering teams around a shared product vision, even in the face of competing priorities and organizational complexity
A bias toward simplicity — someone who defaults to first principles when solving hard problems, knows when to tear down legacy systems rather than patch them, and measures success by how much friction they remove f…

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