Principal Product Operations Manager, Benefits

Responsibilities

• 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.

Requirements

• 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.

Nice-to-Haves

• Experience prototyping with AI (e.g., Claude, Cursor, Codex or similar).
• Experience with service design and/or service blueprinting.
• Experience working in the healthcare or benefits space (PEO, health insurance, etc.); candidates with new product incubation experience in any complex regulated space are strongly encouraged to apply.

Compensation

• $148,000/yr to $182,000/yr in Denver.
• $167,000/yr to $217,000/yr for San Francisco & New York.