Employee Benefits Practice Leader

Description

We are seeking a high-performing Employee Benefits Practice Leader who excels at both driving new business and leading, developing, and elevating a team of sales professionals.

This is a player-coach role for a market-facing producer who operates as an enterprise advisor, someone equally energized by personal production and by building the next generation of top-performing producers. You will lead from the front, shaping strategy, influencing outcomes, and setting the standard for what great looks like in our market.

This leader will focus on building a significant, sustainable book of business while driving sales excellence, strengthening team capability, and delivering consistent, disciplined execution across the practice.

We are not seeking a transactional broker. We are building a team of strategic advisors.

You will operate in a dual capacity:

1. Employee Benefits Advisor / Producer

Drive new revenue by engaging CFOs, CHROs, and executive leadership teams in strategic, consultative 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 

You will establish yourself as a trusted advisor in complex benefit strategy, leading high-stakes discussions, influencing decision-makers, and positioning long-term value over short-term placement.

2. Sales Leader & Practice Builder

Lead and develop a team of Employee Benefits producers by:

• Coaching consultative selling, deal strategy, and executive presence 
• Driving accountability to pipeline activity, conversion, and revenue outcomes 
• Elevating the team from transactional quoting to strategic advisory 
• Creating consistency in sales process, messaging, and go-to-market approach 
• Building a culture of performance, collaboration, and continuous improvement 

You will serve as a coach, raising the bar on individual and team performance while building a scalable, high-performing sales engine.

What You’ll Do

Revenue Growth & Market Leadership

• Own and drive organic growth strategy for the Employee Benefits practice 
• Develop and execute a focused business development strategy targeting mid-market and large employers 
• Personally produce new business while setting the pace and standard for the team 
• Establish a strong market presence as a trusted advisor in complex benefit strategy 
• Influence positioning, differentiation, and competitive strategy within the market 

Team Leadership & Sales Execution

• Coach, mentor, and develop producers at varying experience levels 
• Lead pipeline reviews, deal strategy sessions, and finalist preparation 
• Instill disciplined sales processes, forecasting accuracy, and accountability rhythms 
• Support recruiting, onboarding, and ramping of new producers 
• Build bench strength and succession within the practice 

Strategic Client Engagement

• Lead high-level discovery tied to workforce strategy, risk, and financial performance 
• Design multi-year benefits roadmaps 
• Translate claims data, financial modeling, and market insights into executive-level strategy 
• Engage in complex or at-risk opportunities as a senior advisor and closer 

Cross-Functional Collaboration

• Partner with analytics, actuarial, compliance, and service teams to deliver differentiated solutions 
• Ensure alignment between sales strategy, service delivery, and client outcomes 
• Influence product innovation, vendor strategy, and go-to-market initiatives 
• Act as the bridge between revenue generation and operational excellence 

Practice Leadership & Growth

• Contribute to the overall vision and growth strategy of the Employee Benefits practice 
• Identify market trends, emerging risks, and opportunities for differentiation 
• Help define and operationalize what “great” looks like in sales execution and client engagement 
• Drive consistency, scalability, and long-term value creation across the practice 

What You Bring

• 10+ years of Employee Benefits brokerage or consulting experience 
• Proven track record of generating significant new revenue and sustained book growth 
• Experience leading, mentoring, or coaching producers (formally or informally) 
• Deep expertise in self-funded, level-funded, and fully insured health plans 
• Strong executive presence with boardroom credibility 
• Ability to translate data into strategy and influence senior decision-makers 
• Disciplined pipeline management and sales process rigor 
• Competitive drive balanced with a team-first mindset 
• Active Life & Health license 

Leadership Profile

You are:

• A player-coach who leads by example and earns followership through performance 
• A builder motivated by growing people and a practice 
• A strategic thinker who thrives in complexity and ambiguity 
• A coach at heart who finds fulfillment in developing others 
• A market competitor who plays the long game, focused on sustainable growth and lasting relationships 

Why Gregory & Appel?

• True independence with a client-first strategy 
• Deep analytics, compliance, and population health expertise 
• A collaborative culture where colleagues are our competitive advantage 
• Entrepreneurial environment with meaningful earning potential 
• Long-term wealth-building through sustained book growth 
• A firm committed to helping you build something  lasting 

If you are motivated to win in the market, develop high-performing sales team, and contribute to building something much bigger than yourself, we would welcome a conversation.