Senior Leader, Benefits Advising
Skills
- Leadership of leaders and people development
- Deep experience with small-group health insurance (fully insured and level-funded)
- Track record of retention, revenue growth, and consultative renewals/upsells
- Experience with Salesforce, APIs, and benefits admin platforms
- Ability to design scalable processes and leverage AI/automation
- Strong data-driven decision-making
- Executive presence and cross-functional alignment
- Regulatory and compliance awareness in benefits recommendations
Responsibilities
- Coach and develop 4–6 frontline leaders and their teams of licensed advisors and specialists
- Define and execute renewal and advising strategy to improve retention and expansion
- Deliver on retention targets through tailored, high-quality renewal experiences
- Build playbooks and programs to expand ancillary, tax-advantaged, and retirement offerings
- Partner with Finance and CX leadership to set and achieve revenue goals tied to renewals
- Redesign advisor workflows to integrate AI and automation (e.g., Salesforce, Next Best Action) for higher-value customer engagement
- Ensure compliance, ethics, and trust in advisor recommendations
- Lead change management and continuous improvement to enable team adaptability and performance
- Use customer feedback and data to refine renewal processes and advising outcomes
Education
- Bachelor's degree preferred (or equivalent experience)
- Life & Health insurance license required or willingness to obtain
- Advanced degree (MBA) a plus but not required
Benefits
- Comprehensive health insurance
- 401(k) retirement savings
- Hybrid work schedule with office presence expected for local offices
- Inclusive, collaborative culture and Total Rewards programs
- Professional development and learning opportunities
- Paid time off and employee-focused policies
Average salary estimate
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Gusto was founded in 2011. This company provides payroll processing and employee benefits services. Their headquarters are located in San Francisco, California.
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