Head of Product Operations at Gusto

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

About the Role:

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.

About the 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.

Here’s what you’ll do day-to-day:

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.

Here’s what we're looking for:

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.

Our cash compensation amount for this role is targeted at $189,000/yr to $220,000/yr in Denver & most remote locations, $200,000/yr to $265,000/yr for San Francisco, New York & Seattle. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

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.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

Head of Product Operations

Job Description