Head of Fulfillment - Benefits

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy. 

About the Role:

The Head of Fulfillment will lead the strategy, operations, and execution of our back office fulfillment function, responsible for processing all group and member-level transactions with insurance carriers for our small business customers. This person will be accountable for ensuring timely, accurate, and high-quality transaction delivery, while driving innovation and employee productivity through tooling and automation.

As the Head of Fulfillment, you will shape and scale a high-performing, multi-layered team, drive cross-functional collaboration, and lead process modernization efforts that support Gusto’s growth, improve quality, and unlock new levels of operational excellence.

About the Team:

This is a critical leadership role reporting to the Head of Benefit Operations within CX. Gusto’s CX organization is the heartbeat of our customer promise. With over 300,000 customers and growing, we play a foundational role in ensuring that small businesses and their employees receive the benefits they need—accurately and on time.

Here’s what you’ll do day-to-day:

• Lead a large, distributed fulfillment organization responsible for the end-to-end processing of group and member-level health insurance transactions.
• Drive performance across accuracy, quality, and cycle time metrics, ensuring fulfillment consistently meets SLAs and supports a seamless customer experience.
• Design scalable systems, workflows, and quality controls to reduce rework, improve throughput, and manage seasonal volume spikes such as Open Enrollment.
• Partner closely with Sales, Advising, Onboarding, and Carrier Relations teams to improve intake quality, reduce friction, and streamline cross-functional handoffs.
• Identify and implement AI, automation, and tooling solutions that eliminate manual work and increase employee productivity without sacrificing quality.
• Monitor fulfillment KPIs and proactively use data to identify root causes, prioritize process improvement opportunities, and guide strategic decisions.
• Develop and coach senior leaders to build strong, empowered teams that operate autonomously and with accountability.
• Champion change management, lead system or process migrations, and scale the team’s capacity to handle new product lines, customer journeys, or market segments.
• Foster a high-trust, high-performance culture rooted in operational discipline, team development, and customer impact.

Here’s what we're looking for:

• 10+ years of experience in operations, fulfillment, or insurance administration, with a strong track record of scaling high-volume, detail-oriented teams.
• 5+ years in senior leadership roles managing large, distributed teams (100+ employees) through multiple layers of management.
• Proven success leading operational functions responsible for accuracy, compliance, and on-time delivery in highly transactional environments.
• Deep understanding of health insurance workflows, including group setup, member enrollment, carrier submissions, and ACA compliance.
• Demonstrated experience leveraging technology—AI, automation, or workflow tools—to improve employee productivity and reduce manual effort.
• Skilled in cross-functional collaboration with the ability to build strong relationships across Sales, Product, Engineering, and CX functions.
• Track record of building high-performing teams and developing director-level talent into strategic leaders.
• Data-driven operator with strong analytical skills and experience setting and managing to performance KPIs.
• Confident change leader with experience navigating complexity, ambiguity, and transformation.
• Excellent communication skills with the ability to influence at all levels of the organization.
• Willingness to travel to Gusto’s Centers of Gravity as needed.

Our cash compensation amount for this role is $148,000/yearly to $185,000/yearly in Denver, and $174,000/yearly to $218,000/yearly in San Francisco & New York.