Principal Product Operations Manager

About this role

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:

At Gusto, building a great product and delivering a great service aren't separate tracks — they have to move together, and that's what Service Transformation Product Operations exists to ensure. As a Principal Product Operations Manager, you'll own some of the most cross-cutting work in the Customer Experience org: shaping how new products and features come to market, leading service design that identifies where AI can create the most leverage across the service experience, and operating as the connective tissue between Product, CX, Engineering, Legal, and GTM. This is not a coordination role — you'll drive strategy, build and deploy AI-powered workflows, and bring rigor, creativity, and a bias toward execution to problems that don't yet have obvious answers.

About the Team:

The mission of our Service Transformation (ST) team is to evolve and scale how Gusto delivers outstanding service experiences — and to leverage AI to do it faster and better. We design the systems, processes, and feedback loops that let Gusto's product and service improve together, continuously and reliably, in a way that earns the trust of the small businesses we serve and the Gusto teams who serve them.

ST Product Operations is a cross-functional team sitting at the intersection of Product and CX — responsible not just for making today's experience better, but for shaping how new products and features come to market and how AI changes what great service looks like at scale. If something is broken, we fix it. If something needs to be built, we build it. If a new capability is ready to ship, we make sure it lands well.

Here’s what you’ll do day-to-day:

• Shape and drive strategy at the intersection of Gusto's Product and Service orgs — working closely with Engineering, Design, Product Management, and Customer Experience to improve existing products, launch net-new capabilities, and ensure the service experience scales alongside them.

• Own the end-to-end CX strategy and implementation for net-new product and service launches — from determining how customers will be supported to engaging external partners — while ensuring every new capability meets Gusto's rigorous service standards before and after it goes live.

• Lead strategic service design work alongside Product Management and CX teams — mapping end-to-end service blueprints, identifying where AI can augment or accelerate work done by service teams, and designing the handoffs and escalation logic that keep quality high as automation scales.

• Build, deploy, and iterate on AI-powered workflows that improve how Gusto's service operations run — from automating intake and documentation to designing agentic systems that resolve customer needs faster and more reliably.

• Serve as an AI thought leader within ST Product Operations — identify where AI can accelerate how the team works, set the bar for how those opportunities get acted on, and partner with teammates to propose, build, and adopt solutions that raise the baseline for everyone.

• Provide business insights and recommendations grounded in quantitative and qualitative data to influence both product and service roadmaps. Communicate in a way that drives action — translating complex operational dynamics into clear direction for senior stakeholders.

• Identify and lead cross-functional initiatives that deliver measurable value for customers and for Gusto — building the roadmap, aligning stakeholders, and seeing work through from framing to execution.

Here’s what we're looking for:

• 9+ years of relevant experience in product operations, service design, business operations, strategy, or program management — ideally at a company where you were building or improving a product and service simultaneously.

• Demonstrated track record working at the cutting edge of AI implementation over the last two to three years — you've built agentic workflows, automated service or operational processes using AI tooling, or designed AI-assisted systems in production. You're not learning to do this; you've done it.

• Experience with service design or service blueprinting — you understand how to map a customer journey end-to-end, identify failure points, and design systems that hold up at scale.

• Proven ability to own and improve complex, cross-functional launch or release processes — you know what it takes to bring a product to market well and have built the coordination systems to make it repeatable.

• Strong results-orientation with the ability to extract and interpret data to identify trends and influence decisions — comfortable doing this with or without AI assistance, and fluent in knowing which approach fits the moment.

• Experienced at influencing senior stakeholders across Product, Engineering, CX, Legal, and Compliance — in writing, in design reviews, and in high-stakes forums.

• Experience leading through change — whether guiding a team, driving an organizational transformation, or helping others adapt to new systems and ways of working.

• Highly adaptable and able to create structure

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