Demo

Regional Sales Executive

Questpro
Chicago, IL Full Time
POSTED ON 4/8/2026
AVAILABLE BEFORE 5/6/2026
Business Development Executive

Workers’ Compensation Solutions | Midwest Territory

Remote | Regional Travel

Opportunity Represented by Questpro

Love the Industry. Use Your Network. Sell Something That Actually Helps People.

Are you a relentless prospector who thrives on opening doors and closing deals?

Do you enjoy building relationships across the workers’ compensation ecosystem—connecting with carriers, TPAs, employers, and risk professionals to create meaningful partnerships?

If you’re energized by driving new business, influencing decision-makers, and making an impact, this could be the opportunity you’ve been looking for.

A nationally expanding organization focused on innovative workforce reintegration and return-to-work solutions is seeking a Business Development Executive to drive growth across the Midwest.

This role is ideal for professionals who know and enjoy the workers’ comp industry and want to continue building on the relationships and credibility they’ve developed over time.

The solution you’ll represent helps injured employees remain active and engaged in meaningful work while recovering—supporting better outcomes for workers, employers, and claims partners alike.

Even better, this program is not dependent on restrictive referral panels, making it a natural introduction within the network you’ve already built. Many sales professionals find that conversations happen organically because the solution aligns with the industry’s mission of helping injured workers successfully return to productive lives.

If you’re someone who enjoys owning a territory, developing new partnerships, and turning relationships into long-term business, this opportunity provides the platform to do exactly that.

The Opportunity

You will focus on developing new partnerships across the workers’ compensation and risk management community, introducing organizations to a program that helps injured workers stay active while supporting employers with effective claims management.

This role blends relationship-driven sales with disciplined execution—leveraging industry relationships while using tools and data to maximize productivity and pipeline growth.

You’ll Engage With Decision-makers Across

  • Insurance carriers
  • Third-party administrators
  • Self-insured employers
  • Risk managers and captive groups

Territory & Market Ownership

This role offers the opportunity to build and own your market while leveraging the organization’s national network of industry contacts. You’ll have the credibility of established relationships at your fingertips, giving you a head start in strengthening and expanding existing partnerships.

At the same time, you’ll have the autonomy to generate net-new business, positioning the organization as a trusted resource across the workers’ compensation community within your territory.

Professionals who thrive in this role enjoy developing long-term industry connections, expanding their market influence, and creating sustainable growth through both existing and new client relationships.

What You’ll Be Doing

  • Prospect and develop new business through strategic outreach, networking, referrals, and industry engagement
  • Leverage your existing workers’ compensation network to introduce a differentiated solution
  • Conduct discovery meetings with claims leaders, risk managers, and program decision makers
  • Deliver presentations through in-person meetings, virtual sessions, and industry events
  • Guide prospects through evaluation and partnership development
  • Collaborate with internal teams to ensure smooth client onboarding and program implementation
  • Maintain relationships while identifying additional opportunities for growth
  • Utilize CRM platforms, pipeline tracking, and sales metrics to manage activity, measure progress, and maximize productivity

Ideal Background

  • Proven success in B2B sales
  • Experience within the workers’ compensation, insurance, or risk management industry
  • Established relationships within the carrier, TPA, or employer risk community
  • Strong prospecting mindset with the ability to build pipeline and close new business
  • Comfortable working within a metrics-driven sales environment
  • Experience leveraging CRM systems and sales tools to manage pipeline and performance
  • Excellent presentation and relationship-building skills
  • Self-motivated with an entrepreneurial approach to territory management

What’s Offered

  • Generous compensation and benefits package
  • Opportunity to represent a mission-driven solution supporting injured workers
  • Strong national growth and expanding territories
  • Ability to build and own your market
  • Collaborative culture focused on performance, accountability, and partnership

Territory

Midwest region with travel for client meetings, conferences, and relationship development.

Additional territories are also currently open, including opportunities in the West Coast and Southeast regions for professionals interested in similar roles.

Confidential Inquiries

This opportunity is represented by Questpro, a national search firm specializing in insurance and managed care recruitment.

Professionals currently selling within the workers’ compensation ecosystem who enjoy the industry and the relationships they’ve built—but are interested in representing a solution focused on the well-being and recovery of injured workers—are encouraged to reach out.

Contact: jpomelow@questpro.com

Confidential conversations are welcomed.

Salary.com Estimation for Regional Sales Executive in Chicago, IL
$124,192 to $182,913
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