Head Of Product Operations

About the Role:

The Head of Product Operations at Gusto is a visionary, customer-obsessed leader who drives operational excellence at the intersection of R&D (Product, Engineering, Design, Data Science) and Customer Support and Operations. As Gusto navigates two simultaneous transformations - embedding AI into our customer and agent experiences, and reimagining our own talent model for an AI-first world - the Head of Product Operations will lead with purpose, clarity, and curiosity. You will play a critical part in guiding Gusto's evolution, including how we design, build, and deliver AI powered products and services to customers, while also re-imagining the human-led service experiences, roles, and responsibilities. Additionally, you will elevate the craft and impact of our Product Operations Managers (POMs) team.

About the Team:

This role reports to the Head of Service Transformation and leads a team of approximately 12 Product Operations Managers (POMs). The team partners deeply across Product, CX, Engineering, and Design to ensure a scalable, world-class customer experience and seamless internal operations.

Here's what you'll do day-to-day:

• Partner, align, and influence. Serve as a strategic and operational partner to R&D and CX leadership, aligning product and service strategies to deliver exceptional customer and agent experiences. Foster a culture of collaboration, accountability, and continuous improvement within Product Operations and across partner teams.

• Codify AI-era methods. Shape the next generation of human service roles in an AI-first world, redefining how Gusties and AI work together to deliver better outcomes for customers. Champion AI-driven ways of working across the product and service ecosystem, fostering AI fluency, experimentation, and responsible adoption. Act as a thought leader in building Gusto's internal AI Operations capabilities.

• Coach and lead. Lead, coach, and develop the Product Operations Managers team, building their skills, autonomy, and influence across Gusto's evolving product and service landscape. Own and execute a product operations roadmap that scales service design, operational efficiency, and cross-functional impact.

• Customer first. Obsess over customer experiences and outcomes by bringing together data, insights, feedback, and storytelling to advocate for customer needs and inform product and service decisions.

• Implement and optimize human+ AI systems. Partner closely with R&D (including Service Design) to integrate software, people, and processes into cohesive, end-to-end systems that improve customer experience, operational efficiency, and speed of learning.

Here's what we're looking for:

• 10+ years of experience in product operations, program management, or related functions, including 5+ years leading teams.
• Proven success leading large-scale, cross-functional initiatives in high-growth or transformation environments.
• Demonstrated experience shipping AI-infused services (e.g., conversational self-service, agent assist) with measurable impact.
• Experience shaping product, service, and operational experiences that blend human, software, and AI capabilities.
• Exceptional communicator and relationship builder, with the ability to influence at all levels of the organization.
• Deep empathy for both customers and internal teams, with a bias for action, continuous learning, and customer-driven decision-making.
• Passion for developing people and evolving organizational capabilities in an AI-first world.

Our cash compensation amount for this role is targeted at $189,000/yr to $220,000/yr in Denver & most remote locations, $200,000/yr to $265,000/yr for San Francisco, New York & Seattle. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.