Principal Product Operations Manager, Benefits

About the Role

Are you looking for an opportunity to transform a business? Gusto is looking for a strategic, customer-focused leader to leverage customer feedback and operational key metrics to develop actionable insights and strategies that shape our product and service, and positively impact customer love.

Working with the Product, Engineering, Design and Customer Experience teams, you will be expected to tackle both highly strategic and deeply operational initiatives to deliver value for customers and Gusto. You’ll be customer-obsessed, business-minded, strategic, detail-oriented, and highly creative.

In this role, you'll help stand up the operational and service foundation for a new Gusto product, using both deep human judgment and emerging AI tools to move faster and make better decisions. If this sounds exciting to you, we’d love to connect!

About the Team

The Benefits Product Operations team at Gusto is made up of committed, creative, collaborative people who care deeply about our mission to enable Benefits for all small and mid-sized businesses and their employees. We’re a highly cross-functional team focused on ensuring our product and service are co-designed and co-developed along the product lifecycle to deliver a best in class customer experience; Gusto is listening to, synthesizing and acting on customer and front-line team feedback; and that cross-functional teams are collaborating and swimming together to build the best version of Gusto for our customers.

Here’s what you’ll do day-to-day

• Shape and support product development and its integration into service strategy for existing customers across the product lifecycle, in collaboration with Engineering, Design, Product Management, and Customer Experience teams.
• Understand our product and end-to-end service experience and organizations in intimate detail, including internal and external pain points and feedback.  Collaborate to ensure customer support considerations are integrated into broader company decisions.
• Lead and partner on product launches between Product Management and Customer Experience (CX) teams to ensure readiness and deliver insights post-launch to ensure a positive experience for customers and internal teams.
• Provide business insights and recommendations based on quantitative and qualitative data to influence strategy and operational design in both product and service roadmaps.
• Identify and drive cross-functional initiatives that will deliver value for customers and Gusto. Help develop and communicate a clear roadmap for enhancing service capabilities and experiences.
• Hypothesis-driven problem solving to drive our business.
• Contribute to advancing the Product Operations craft at Gusto and build AI fluency within the team:
  • Model how to use AI tools to accelerate service design, insight synthesis, and agent-driven operational workflows.
  • Identify and build AI-assisted operational workflows, including agents, to accelerate VoC synthesis, launch readiness monitoring, and cross-functional signal aggregation.
  • Use AI tools to prototype service solutions and surface requirements faster, compressing the feedback loop between customer signal and product/service response — before full engineering investment.

Here’s what we're looking for

• 10+ years of relevant work experience at growing startups in operating roles (i.e., biz ops/strategy roles, product operations, project/program management, and/or consulting):
  • Experience scaling service strategy alongside growing SaaS products, including incubating products, building and managing product betas, and/or integrating new products into a scalable best-in-class service model.
  • Highly adaptable and resilient to changes in business needs or requirements, with the ability to navigate challenges and make decisions even when information is incomplete.
• Demonstrated self-starter and organized problem-solver. Self-sufficient, resourceful, and bias for action towards continuous improvement.
• Experienced with managing a variety of cross-functional stakeholders on complex strategic initiatives, including influencing senior leaders in Product or Customer Experience orgs.
• Strong data literacy and results-orientation, with the ability to identify the right questions, interpret quantitative and qualitative signals, and translate findings into decisions — including comfort using AI-assisted tools for analysis and synthesis.
• Excellent written and verbal communication skills, with the ability to effectively communicate complex subjects to both technical and non-technical audiences.
• Demonstrated AI fluency in an operational and product context — comfort using AI tools to synthesize qualitative data, identify automation opportunities in service workflows, and building or directing AI agents to reduce manual operational lift:
  • Experience prototyping with AI (e.g., Claude, Cursor, Codex or similar) is a plus.
• Experience with service design and/or service blueprinting.
• Experience working in the healthcare or benefits space (PEO, health insurance, etc.) is a plus; candidates with new product incubation experience in any complex regulated space are strongly encouraged to apply.

Our cash compensation amount for this role is $148,000/yr to $182,000/yr in Denver, and $167,000/yr to $217,000/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.