$120K - 180K a year
Lead Chicago market expansion, shape strategy, recruit and onboard sales team, influence M&A, and grow into Sales Team Leader role.
6+ years of employee benefits sales experience, active insurance license, stable work history, strong closing record, leadership interest, and Chicago-based or willing to relocate.
Lead Employee Benefits Producer – Chicago Expansion Join a rapidly growing, employee-owned insurance organization shaping the future of the Midwest market! Are you an accomplished Employee Benefits Producer ready to lead expansion efforts in a dynamic, growth-focused environment? We’re partnering with a Top 40 national insurance agency undergoing significant westward growth, with Chicago, IL as a key strategic hub. This is a high-impact, equity-eligible opportunity for a proven producer to: • Anchor the Chicago market expansion • Shape market strategy and lead recruiting/onboarding • Influence M&A evaluations (tuck-ins and acquisitions) • Grow into a Sales Team Leader role Your Impact You’ll leverage a robust support system, wide-open territories, and cross-selling opportunities across P&C, while being part of a collaborative leadership team that values your expertise and entrepreneurial mindset. What We’re Looking For • 6+ years of Employee Benefits sales experience (agency preferred, carrier considered) • 3+ years in a stable role (no frequent job changes) • Strong producer/closer track record (mid–large group: 100+ lives) • Licensed and actively working in insurance • Based in or willing to relocate to Chicago (travel to HQ in South Bend, IN quarterly) • Proven relationship builder with consultative sales approach • Interest in mentorship, leadership, or market expansion Ready to lead, grow, and shape a new market? Apply now and be part of a team where your expertise drives success.
This job posting was last updated on 9/9/2025