Demo

Regional VP of Sales | Midwest

Questpro
Chicago, IL Full Time
POSTED ON 6/3/2026
AVAILABLE BEFORE 7/2/2026
Remote | Controlled Travel Required

Ready to Leverage the Relationships You've Spent Years Building?

If you've developed strong relationships with insurance carriers, TPAs, self-insured employers, SIU leaders, claims executives, risk managers, or other industry decision-makers, this is an opportunity to put those connections to work with a highly respected national provider of investigative and risk management solutions.

Our client has built an outstanding reputation serving the insurance, workers' compensation, claims, risk management, and corporate security markets for more than two decades. As they continue to expand, they are seeking a relationship-driven sales professional who can open doors, create opportunities, and grow strategic partnerships across key markets.

What Makes This Opportunity Different?

This is not a transactional sales role.

Success comes from leveraging existing industry relationships, understanding client challenges, and providing solutions that help organizations manage risk, investigate claims, combat fraud, and make better business decisions.

The Ideal Candidate Will Have Relationships Within

  • Insurance Carriers
  • Third-Party Administrators (TPAs)
  • Self-Insured Employers
  • SIU and Fraud Investigation Units
  • Claims Organizations
  • Risk Management Departments
  • Public Entities
  • Transportation and Trucking Organizations
  • Corporate Security and Loss Prevention Teams

Solutions You'll Represent

  • Investigative and Surveillance Services
  • Field Video Retrieval Solutions
  • Internet and Social Media Intelligence
  • Background Investigations
  • Threat Assessment Services
  • Claims and Fraud Support Solutions
  • Additional Risk Management and Intelligence Services

What You'll Do

  • Develop and expand relationships with carriers, TPAs, self-insured employers, and other industry stakeholders
  • Generate new business opportunities through existing networks, referrals, prospecting, and industry engagement
  • Meet with senior claims, SIU, risk management, and operational leaders
  • Conduct presentations and consultative sales discussions
  • Attend conferences, association meetings, and networking events
  • Maintain and manage sales activity through CRM systems
  • Serve as a trusted resource to clients and prospects

Ideal Background

We Welcome Professionals From

  • Private Investigations
  • Workers’ Compensation Services
  • Property & Casualty Insurance
  • Claims Management Organizations
  • SIU and Fraud-Related Services
  • Risk Management Solutions
  • Corporate Security Services
  • Insurance Vendor and Service Organizations

Qualifications

  • Proven success in business development or sales
  • Existing industry relationships strongly preferred
  • Demonstrated ability to engage and influence decision-makers
  • Strong communication and presentation skills
  • Self-motivated with a hunter mentality
  • Ability to work independently in a remote environment
  • College degree preferred but not required

Compensation & Benefits

  • Competitive base salary
  • Attractive bonus and incentive structure
  • Excellent earning potential for high performers
  • Car allowance
  • Health, dental, and vision benefits
  • 401(k) with company match
  • Paid vacation

If you're successful in sales today but looking for a stronger platform, broader opportunities, and the ability to leverage the relationships you've spent years building, we'd welcome a confidential conversation.

Recruiter Contact

Jillanna Pomelow

Questpro

jpomelow@questpro.com

Salary.com Estimation for Regional VP of Sales | Midwest in Chicago, IL
$62,885 to $73,242
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