Senior Principal Product Manager, Gusto
AI Enabled Workforce
Salary dependent on location
More information about location
2-3 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
Salary dependent on location
More information about location
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- We’re looking for a leader who can balance strategic influence with hands-on craft—someone who can guide senior Gusto leaders through AI-native data strategy, coach data scientists on impactful problem solving, and dive in to drive forward statistically rigorous analyses when needed
- Visionary Product Leadership: 10+ years of experience in product management, with a proven track record of leading high-stakes internal platforms, RevOps, or Service technology at scale
- AI Builder & Strategist: AI/ML specialist with deep expertise in LLMs and agentic workflows, building and shipping custom AI solutions that transform how teams work and scale
- Systems Thinker: You see the "big picture" of how data and tools flow across a company and can architect solutions that solve for the end-to-end customer journey
- Change Agent: Experience leading large-scale organizational transformations or merging complex technical teams into a unified organization
- Human-Centric Empathy: A passion for "the work of work"—you are obsessed with making tools that employees love to use and that remove the friction from their daily lives
- Strategic Execution: The ability to balance long-term 18-month missions (like #OneGusto) with the immediate tactical needs of a fast-growing GTM engine
What the job involves
- At Gusto, we believe the next frontier of competitive advantage is the intelligence of the systems that power our people
- As the Sr Principal PM, AI Workforce Enablement, you are the architect of the "Superhuman Agent." You won't just manage tools; you will redefine the relationship between Gusto’s workforce and technology
- You are responsible for evolving our internal foundation into a proactive, agentic platform where AI handles the cognitive load, allowing our Go-to-Market (GTM) and Service teams to focus on high-value human connection
- You will lead the transition of our legacy ecosystem into a future-state "exoskeleton" that empowers every employee to deliver an unparalleled, frictionless experience to our customers
- Gusto is looking for a hands-on builder to take on this leadership mantle as we rethink how people grow in an AI-native company. This role is not just about designing the systems that shape growth day-to-day, but the actual mechanics of work
- You will be responsible for building new architecture and tearing down what no longer serves us. The goal is simple but hard: make growth obvious, continuous, and hard to avoid
- The Unified Service Platform (USP) product team serves as Gusto’s architectural backbone, responsible for engineering the intelligent, AI-driven ecosystem that brings GTM and Service operations into alignment
- Our mission is to replace fragmented point solutions with a singular System of Intelligence—a digital exoskeleton that strips away administrative friction so our teams can focus on what matters most: our customers
- Through our commitment to a #OneGusto experience, we provide the platform that ensures every internal interaction is backed by the full context of the customer journey
- We are an AI-native team building "agentic" solutions that transform how work happens. By mastering the AI-Human-AI loop, we own the delivery of a seamless, cross-channel journey across voice, chat, and email
- Our goal is to ensure that our internal technical excellence creates an instant, easy and effortless experience for every business Gusto serves
- Architect of the "System of Intelligence": Lead the evolution of Gusto’s internal workspace by integrating 1P (first-party) and 3P (third-party) systems into a unified platform. Transform CRM into a proactive platform that anticipates agent needs and triggers automated workflows across the entire tech stack before manual intervention is required
- Design the Future-State Agent Experience: Build the product mechanics for a symbiotic "AI-Human-AI" loop, where intelligent systems handle high-volume tasks and documentation, elevating our human experts to focus on high-value, high-empathy problem solving
- Engineer the "Digital Exoskeleton": Ship real-time, context-aware assistance and agentic tools that eliminate cognitive load, enabling every Gustie to operate with "superhuman" speed and accuracy across voice, chat, and email
- Lead with Technical Craft: Partner with Data Science and Engineering to bridge the gap between high-level AI strategy and rigorous execution, ensuring our models drive measurable gains in both agent productivity and employee sentiment
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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