Head of Fulfillment - Benefits

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. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.