Benefits Escalation Services Manager

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: The Escalations Services team is the engine that ensures our customers have peace of mind when it matters most: accessing their health insurance. We are seeking an emerging leader to guide and scale this team, delivering a best-in-class experience for thousands of small businesses and their employees. In this role, you will lead a team of 10–15 Operations Specialists (Individual Contributors) responsible for the execution and delivery of benefits administration- working directly with health insurance carriers to ensure timely and accurate coverage. This is a hands-on leadership role for the modern era. We are looking for a results-oriented owner who combines deep industry knowledge with an AI-native mindset. You will balance day-to-day tactical execution- like workflow management and carrier communications- with the strategic goal of leveraging technology to build a seamless, scalable onboarding journey. Here’s what you’ll do day-to-day:

Lead & Coach: Directly manage a team of ~15 Operations Specialists. Create an environment of continuous development through weekly 1:1s, real-time mentoring, and actionable feedback to help individuals develop their careers. Drive Operational Execution: Ensure that benefit enrollments are processed in a timely and accurate manner within agreed-upon SLAs. Manage daily workflows to balance speed with quality. Innovate with AI & Automation: Actively identify opportunities to leverage AI tools and automation to reduce manual administrative burden. You will coach your team on how to "work smarter" by adopting new technologies to streamline carrier interactions. Own Performance & Metrics: Take responsibility for your team’s execution of monthly, quarterly, and annual objectives. Use scalable systems and data to monitor performance, ensuring the team meets or exceeds their goals. Strategic Problem Solving: Serve as the primary escalation point for high-impact cases to remove roadblocks for your team, while simultaneously conducting root cause analysis to drive systemic improvements and operational efficiency. Champion Change: Lead change management efforts by translating high-level company initiatives and OKRs into daily actions. Foster a culture of engagement where the team feels empowered to put customers first amidst a fast-paced, evolving environment.

Industry Expertise (Must Have): 3+ years of experience in Benefits Administration, Health Insurance (Carrier side), or with a Benefits Broker (e.g., ADP, Rippling, Aetna, Cigna). You understand the lifecycle of a benefit order. 3+ years of experience leading projects, mentoring