Benefits Escalation Services Manager
Gusto is a payroll and HR platform that helps small businesses pay domestic and international employees, manage benefits, and automate compliance.
Projects
About Gusto
Gusto serves small and mid-sized businesses with payroll processing, employee benefits administration, and HR tools in one platform. Users can run payroll, manage health insurance, hire globally, and pay international contractors in local currency or USDC stablecoins. The platform automates payroll tax filings across multiple states and integrates with tools like QuickBooks and Xero.
Skills
About the Role
You will lead a team of 10–15 Operations Specialists responsible for the execution and delivery of benefits administration, working directly with health insurance carriers to ensure timely and accurate coverage. You will directly manage your team through weekly 1:1s, real-time mentoring, and actionable feedback to help individuals develop their careers. You will ensure benefit enrollments are processed in a timely and accurate manner within agreed-upon SLAs and manage daily workflows to balance speed with quality. You will actively identify opportunities to leverage AI tools and automation to reduce manual administrative burden and coach your team on adopting new technologies to streamline carrier interactions. You will take responsibility for your team's execution of monthly, quarterly, and annual objectives, using scalable systems and data to monitor performance. You will serve as the primary escalation point for high-impact cases, conducting root cause analysis to drive systemic improvements. You will lead change management efforts by translating high-level company initiatives and OKRs into daily actions and foster a culture of engagement where the team puts customers first.
Requirements
- 3+ years of experience in Benefits Administration, Health Insurance (Carrier side), or with a Benefits Broker
- Understanding of the lifecycle of a benefit order
- 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
- Comfortable using LLMs (e.g., ChatGPT, Claude, Gemini) and other modern tools
- Comfortable working with data (Excel, Salesforce/SFDC, Tableau)
- Experience with change management
- Creative thinker with a first-principles approach to solving complex enrollment issues
- Bachelor's degree preferred, or equivalent relevant work experience
- Experience in a high-growth startup environment is a bonus
- Salesforce (SFDC) reporting and dashboards experience is a bonus
- Prompt engineering or workflow optimization using generative AI is a bonus
Responsibilities
- Lead and coach a team of ~15 Operations Specialists through weekly 1:1s, real-time mentoring, and actionable feedback
- Ensure benefit enrollments are processed in a timely and accurate manner within agreed-upon SLAs
- Manage daily workflows to balance speed with quality
- Identify opportunities to leverage AI tools and automation to reduce manual administrative burden
- Coach the team on adopting new technologies to streamline carrier interactions
- Own the team's execution of monthly, quarterly, and annual objectives
- Use scalable systems and data to monitor performance and ensure goals are met or exceeded
- Serve as the primary escalation point for high-impact cases
- Conduct root cause analysis to drive systemic improvements and operational efficiency
- Lead change management efforts by translating company initiatives and OKRs into daily actions
Benefits
- Competitive base pay
- Equity (RSUs)
- Benefits for full-time employees