Description
At Gregory & Appel, we don’t compete on volume, we compete on strategy. As one of the largest independent insurance advisory firms in the Midwest, our independence allows us to deliver objective guidance, sophisticated analytics, and long-term partnership without shareholder pressure.
We are seeking a high-performing Employee Benefits Sales Executive who thrives in complex environments and is motivated to build a significant, sustainable book of business serving mid-market and large employers. This is a growth role for a market-facing producer who sees themselves as an enterprise advisor, who values the long-game, serving our clients with value-added benefit strategy with continuous renewal and retention in mind. We are not seeking a traditional transactional broker.
The Opportunity
You will drive new revenue by engaging CFOs, CHROs, and executive leadership teams in strategic conversations around:
- Self-funded and alternative funding strategies
- Cost containment and multi-year healthcare planning
- Pharmacy and clinical risk management
- Population health and workforce engagement
- Regulatory and compliance risk mitigation
We are looking for a disciplined, proactive, consultative, sales leader who:
- Targets complex employers to serve with our innovative benefit solutions
- Is comfortable and thrives navigating sophisticated procurement cycles
- Can translate claims data and financial modeling into board-level strategy
- Builds trust through value-added consultation through insight, not transactional quoting
What You’ll Do
- Develop and execute a focused business development strategy targeting mid-market and large group employers
- Lead consultative discovery sessions tied to workforce strategy and financial performance
- Design multi-year benefits roadmaps aligned with talent, culture, and EBITDA objectives
- Partner with our internal analytics, actuarial, compliance, and service teams to deliver differentiated solutions
- Build a book of business with long-term retention and revenue growth objectives
- Serve as a strategic advisor accountable for both growth and client outcomes
What You Bring
- 8+ years of Employee Benefits brokerage or consulting experience
- Demonstrated history of generating significant new revenue
- Expertise in self-funded, level-funded, and fully insured health plans
- Strong executive presence and boardroom credibility
- Disciplined pipeline management and sales process rigor
- Resilience, competitiveness, and a growth mindset
- Active Life & Health license
Why Gregory & Appel?
- True independence, with a client-first strategy
- Deep analytics, compliance, and population health resources
- Collaborative culture where colleagues are our competitive advantage
- Entrepreneurial environment with meaningful earning potential
- Long-term wealth-building opportunity through sustained book growth
- A firm committed to helping you build something lasting
If you are motivated to compete at a high level, build a substantial book of business, and serve clients through strategic partnership rather than product placement, we would welcome a conversation.
Skills Required
- 8+ years of Employee Benefits brokerage or consulting experience
- Demonstrated history of generating significant new revenue
- Expertise in self-funded, level-funded, and fully insured health plans
- Active Life & Health license
- Strong executive presence and boardroom credibility
- Disciplined pipeline management and sales process rigor
- Ability to translate claims data and financial modeling into board-level strategy
- Resilience, competitiveness, and a growth mindset
What We Do
Gregory & Appel is a fiercely independent risk management advisor, proactively guiding people and businesses through the complexities of insurance and employee benefits with smart, future-focused solutions. Now in their second century, Gregory & Appel professionals are forward thinking and offer strategic resources to protect their clients' assets and human capital while minimizing risk and ensuring business sustainability.
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