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Gusto

Principal Product Operations Manager, Benefits

Sorry, this job was removed at 12:14 a.m. (EST) on Friday, Oct 10, 2025
Easy Apply
Remote or Hybrid
7 Locations
Easy Apply
Remote or Hybrid
7 Locations

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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:

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. 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 uplevel the work of the team. 

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, to include 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. 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, to include influencing senior leaders in Product or Customer Experience orgs
  • Strong results-orientation and direct experience in pulling and utilizing data (SQL) to identify critical trends and make/influence critical decisions. Skillful in setting goals based on the desired end state and planning strategies to achieve them.
  • Excellent written and verbal communication skills and ability to effectively communicate complex subjects to both technical and non-technical audiences
  • Experience working in the healthcare or benefits space (PEO, health insurance, 401k etc.) 
  • Experience with service design and/or service blueprinting

Our cash compensation amount for this role is $148,000/yr to $182,000/yr in Denver & most major metro locations, 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.

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.

Gusto New York, New York, USA Office

Located in the heard of midtown, Penn 1 is redefining what it means to work in the Penn District. Gusto's 52nd Floor office boasts amazing views of the city and is centrally located with access to subways, LIRR, and buses, while some Gusties also bike to work!

What you need to know about the NYC Tech Scene

As the undisputed financial capital of the world, New York City is an epicenter of startup funding activity. The city has a thriving fintech scene and is a major player in verticals ranging from AI to biotech, cybersecurity and digital media. It also has universities like NYU, Columbia and Cornell Tech attracting students and researchers from across the globe, providing the ecosystem with a constant influx of world-class talent. And its East Coast location and three international airports make it a perfect spot for European companies establishing a foothold in the United States.

Key Facts About NYC Tech

  • Number of Tech Workers: 549,200; 6% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Capgemini, Bloomberg, IBM, Spotify
  • Key Industries: Artificial intelligence, Fintech
  • Funding Landscape: $25.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Greycroft, Thrive Capital, Union Square Ventures, FirstMark Capital, Tiger Global Management, Tribeca Venture Partners, Insight Partners, Two Sigma Ventures
  • Research Centers and Universities: Columbia University, New York University, Fordham University, CUNY, AI Now Institute, Flatiron Institute, C.N. Yang Institute for Theoretical Physics, NASA Space Radiation Laboratory

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