Sales Executive

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Location: Chicago, IL | Hybrid (Local Presence Required)

About Us

As an employee-owned organization, we believe in empowering our people to take charge of their careers. Our mission is simple: provide exceptional service while living our Core Values:

• Create a Great Experience
• Do the Right Thing
• Play for Each Other
• Pursue Growth
• Own Your Future

With a national footprint and deep-rooted expertise, we’re expanding westward—and Chicago is our next major growth hub. We're building from the ground up and seeking an experienced, entrepreneurial Employee Benefits Sales Executive to help lead the charge.

Why This Role Matters

This is more than a traditional producer role. As the anchor hire in a new market, you will play a pivotal role in shaping our presence in Chicago:

• Lead market strategy and territory development
• Influence office growth, recruiting, and onboarding
• Participate in strategic M&A conversations
• Grow into a Sales Team Leader with leadership and equity potential

Backed by a Top 40 national insurance agency , a collaborative leadership team, and direct access to cross-selling in P&C, you’ll have the tools and freedom to build your legacy.

What You'll Do

• Cultivate new relationships with C-suite, HR, and benefits decision-makers
• Leverage referrals, networks, industry events, and outbound outreach to generate leads
• Actively maintain a robust pipeline (3x annual sales goal minimum)
• Present tailored, consultative insurance and risk management strategies
• Utilize sales enablement tools and CRM to track activity and progress
• Serve as the account lead, supported by a dedicated client service team
• Conduct risk analysis, program reviews, and propose innovative solutions
• Educate clients on marketplace options, compliance changes, and cost-containment strategies
• Partner with internal teams to deliver seamless renewals, carrier negotiations, and implementation
• Maintain high retention and satisfaction through consistent engagement
• Contribute to the development of go-to-market plans for Chicago
• Mentor junior producers and participate in talent recruitment
• Collaborate with executive leadership and HQ on quarterly initiatives
• Help evaluate local acquisition or tuck-in opportunities

What Makes You a Great Fit

• 6+ years of agency-side insurance sales experience in Employee Benefits
• Proven success in the middle-to-large group market (100+ lives)
• Licensed in Life & Health (or willing to obtain within 60 days)
• 3+ years of tenure in a previous role (no frequent job changes)
• Based in or willing to relocate to Chicago, IL
• Willing to travel to Corporate HQ in South Bend, IN quarterly
• Strong consultative selling and closing skills
• Strong professional network in the Illinois market
• Leadership qualities or interest in mentoring a growing team
• Background in both sales and client strategy or servicing

What We Offer

• Competitive base + uncapped commission structure
• Equity opportunity based on performance
• Direct support from marketing, sales enablement, and executive leadership
• Full suite of benefits including health, dental, vision, 401(k) with match
• Flexibility and autonomy to build your market your way
• The chance to own your future as we grow this region together

Are you ready to create something impactful in Chicago?

We’re looking for a passionate, connected, and entrepreneurial Employee Benefits leader who’s ready to go beyond “business as usual.”

Apply now or reach out to learn more about how you can Own Your Future with us.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales, Management, and Strategy/Planning

• Industries

  Insurance

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