Demo

Senior Sales Executive | WC Bill Review | Middle Market

Questpro
Chicago, IL Full Time
POSTED ON 5/10/2026
AVAILABLE BEFORE 7/3/2026
100% Remote | Domiciled in Central Eastern Timezone preferred

Calling High-Impact Program Sales Producers

Got a seat at the table but limited upside? Here’s your opportunity to truly share in the feast.

Questpro is conducting an exclusive search for a Senior Sales Executive to join an established, privately held organization widely recognized as a gold-standard provider within the middle-market WC Bill Review space. Unlike competitors that prioritize enterprise accounts, this firm is purpose-built for small-to-mid-sized TPAs, carriers, and self-insured groups — and that focus wins.

Key Differentiators

Technology platform includes modern WC Bill Review software — familiarity is a plus

True middle-market alignment → less competition

Make meaningful client impact → not just another vendor; you are their WC Bill Review hero

Direct access to decision-makers → shorter sales cycles

High-margin, customized solutions → easier sell with larger markups 💲 and fewer pricing restrictions 🔓

Strong retention in an underserved, high-demand market

You’ll be positioned as a strategic solution — not a commodity.

Ideal Background

We’re seeking a roll-up-your-sleeves individual contributor with an ownership mindset who brings:

  • WC Bill Review program sales experience preferred

(OR adjacent program sales in WC claims, PBM, software, or cost containment services)

  • Established network within middle-market TPAs, carriers, and self-insureds
  • Proven new-logo acquisition success
  • Ability to convert long-standing relationships into rapid revenue traction and new business wins
  • True hunter mentality with operational fluency
  • Entrepreneurial, growth-oriented mindset

Production = Partner-Level Upside

This isn’t just a comp plan $$ it’s participation:

  • Share directly in the growth you create
  • Fast-track path toward equity participation
  • Realistic trajectory toward a future monetization event
  • Above-market commission structure
  • Performance-based profitability participation
  • Opportunity to influence strategy and direction

Build it. Grow it. Benefit from it.

  • Footnote – For Sales Producers & WC Bill Review Ops SMEs

Are you a WC Bill Review Operations SME who built the engine… while others captured the upside? If you’ve spent years cultivating trusted customer relationships — and watched sales leadership or ownership capture a larger share of the reward — this may be your moment to monetize the credibility and relationships you’ve built.

Your credibility. Your relationships. Your opportunity.

We welcome conversations with both revenue producers and operational WC Bill Review experts ready to step into a growth and upside-driven environment.

Non-compete? Let’s talk anyway. Every situation is unique, and all inquiries are handled confidentially.

To Learn More / Schedule a Confidential Conversation

📩 Email: jpomelow@questpro.com

📅 Schedule directly: https://calendly.com/go2recruiter/22

Let’s explore whether this is your next high-impact move.

Salary.com Estimation for Senior Sales Executive | WC Bill Review | Middle Market in Chicago, IL
$73,245 to $102,494
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