Principal Product Operations Manager, Benefits

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. 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 . AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. 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