Head of Product Operations, Gusto
$189-220k
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
$189-220k
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
- 10+ years of experience in product operations, program management, or related functions, including 5+ years leading teams
- Proven success leading large-scale, cross-functional initiatives in high-growth or transformation environments
- Demonstrated experience shipping AI-infused services (e.g., conversational self-service, agent assist) with measurable impact
- Experience shaping product, service, and operational experiences that blend human, software, and AI capabilities
- Exceptional communicator and relationship builder, with the ability to influence at all levels of the organization
- Deep empathy for both customers and internal teams, with a bias for action, continuous learning, and customer-driven decision-making
- Passion for developing people and evolving organizational capabilities in an AI-first world
- When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees
What the job involves
- The Head of Product Operations at Gusto is a visionary, customer-obsessed leader who drives operational excellence at the intersection of R&D (Product, Engineering, Design, Data Science) and Customer Support and Operations
- As Gusto navigates two simultaneous transformations — embedding AI into our customer and agent experiences, and reimagining our own talent model for an AI-first world — the Head of Product Operations will lead with purpose, clarity, and curiosity
- You will play a critical part in guiding Gusto’s evolution, including how we design, build, and deliver AI powered products and services to customers, while also re-imagining the human-led service experiences, roles, and responsibilities
- Additionally, you will elevate the craft and impact of our Product Operations Managers (POMs) team
- This role reports to the Head of Service Transformation and leads a team of approximately 12 Product Operations Managers (POMs)
- The team partners deeply across Product, CX, Engineering, and Design to ensure a scalable, world-class customer experience and seamless internal operations
- Partner, align, and influence. Serve as a strategic and operational partner to R&D and CX leadership, aligning product and service strategies to deliver exceptional customer and agent experiences. Foster a culture of collaboration, accountability, and continuous improvement within Product Operations and across partner teams
- Codify AI-era methods. Shape the next generation of human service roles in an AI-first world, redefining how Gusties and AI work together to deliver better outcomes for customers. Champion AI-driven ways of working across the product and service ecosystem, fostering AI fluency, experimentation, and responsible adoption. Act as a thought leader in building Gusto’s internal AI Operations capabilities
- Coach and lead. Lead, coach, and develop the Product Operations Managers team, building their skills, autonomy, and influence across Gusto’s evolving product and service landscape. Own and execute a product operations roadmap that scales service design, operational efficiency, and cross-functional impact
- Customer first. Obsess over customer experiences and outcomes by bringing together data, insights, feedback, and storytelling to advocate for customer needs and inform product and service decisions
- Implement and optimize human + AI systems. Partner closely with R&D (including Service Design) to integrate software, people, and processes into cohesive, end-to-end systems that improve customer experience, operational efficiency, and speed of learning
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.
Salary benchmarks
We don't have enough data yet to provide salary benchmarks for this role.
Submit your salary to help other candidates with crowdsourced salary estimates.
Share this job
View 56 more jobs at Gusto