Head of Product Operations

Gusto • San Francisco, NY

22d • $189,000 - $265,000 • Hybrid

About The Position

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: 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.

Requirements

• 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.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed