Benefits Advising Leader
Gusto is a payroll and HR platform that helps small businesses pay domestic and international employees, manage benefits, and automate compliance.
Maintainer signals as of 8/14/2026
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
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You will lead a licensed benefits advisory organization, coach 10–15 advisors and specialists, drive retention and revenue growth, improve renewal processes and customer experience, manage cross-functional initiatives, guide change, and integrate AI tools into advising workflows.
Requirements
- 4–6 years of formal leadership experience in benefits advisory, customer success, renewals, or a similar field
- Small group health insurance experience
- Revenue growth, customer retention, and expansion experience
- Analytical and strategic thinking
- Operational and process improvement skills
- Strategic AI tool evaluation and adoption
- Experience with Salesforce, APIs, and benefits administration platforms
- Executive presence
- Life & Health insurance license
Responsibilities
- Coach advisors and specialists through regular one-on-ones and performance reviews
- Drive customer retention and revenue growth through high-quality renewal experiences
- Use customer feedback and data to improve advising processes
- Manage large-scale cross-functional initiatives
- Lead organizational change
- Build trust, feedback, and continuous learning
- Partner with Product, Carrier Ops, Sales, and customer experience teams
- Identify AI opportunities and improve customer engagement
Benefits
- Equity (RSUs)
- Hybrid work schedule
