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.

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.

Qualifications

• 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.

Skills

• 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.

Benefits

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

Pay

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).

Schedule

The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Minor Metadata

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.

Create a Job Alert

Interested in building your career at Gusto, Inc.? Get future opportunities sent straight to your email.

Apply for this job*