Benefit Services Manager

About Gusto 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: 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. About the Team: The Benefit Operations Fulfillment 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. 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. Here’s what we're looking for: 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. Leadership Potential: 1–3 years of experience leading projects, mentoring peers, or serving as a Team Lead/Subject Matter Expert. Proven track record of hiring or training top talent is a plus. AI Fluency Digital Agility: You embrace the "AI-native" workforce. You are comfortable using LLMs (e.g., ChatGPT, Claude, Gemini) and other modern tools to draft communications, summarize data, and solve problems faster. You don't just accept processes as they are; you look for ways to automate them. Data-Driven Mindset: Comfortable working with data (Excel, Salesforce/SFDC, Tableau) to measure performance and make objective decisions. Operational Agility: Experience with change management; you can inspire buy-in and keep a team organized amidst competing priorities. Problem Solver: A creative thinker who uses a "first-principles" approach to solve complex enrollment issues while maintaining a customer-first mentality. Education: Bachelor’s degree preferred, or equivalent relevant work experience. Bonus Points: Experience in a high-growth startup environment. Specific experience with Salesforce (SFDC) reporting and dashboard ... (truncated, view full listing at source)