Regional Vice President, Sales – Chicago
Transforming Employee Health Benefits for the Greater Good

At ParetoHealth, we are on a mission to level the playing field. For too long, small and midsize businesses have been stuck in a broken system, facing rising health benefit costs with few options. We’re changing that. Through innovative, strategic cost-control solutions, and an ecosystem of trusted partners, we give businesses the power and flexibility of self-insurance—allowing them to take control of their healthcare spend while delivering effective, affordable coverage.

At Pareto, we’re on the right side of the fight—working for the greater good to ensure employers and employees can access sustainable healthcare options for years to come. If you are an A player, high achieving sales professional who wants to disrupt the healthcare landscape we want to talk to you!

Who we want

As a Regional Vice President of Sales (RVP), you’ll be a key force driving our mission forward. Reporting to the sales leader with the Midwest Region, you’ll focus on developing strong relationships with insurance brokers and benefits consultants, serving as a trusted advisor to deliver solutions that reduce risk, maximize cost efficiency, and give small and midsize businesses the options typically reserved for larger firms.

This role is based within the sales territory with frequent local travel, putting you face-to-face with the decision-makers, partners, and brokers who are ready to transform how they approach employee healthcare.

A Day in the Life

Building Trusted Partnerships:
You’ll spend your day fostering relationships with key broker partners—educating them on Pareto’s self-insurance model and helping them identify employers who can benefit from a better way to manage their health benefits. You are the bridge between their challenges and our solutions.

Creating Impactful Solutions:
Dive deep into prospective employers’ needs, providing clarity on how Pareto’s innovative cost-control programs reduce risk and drive significant savings. You’re not just selling; you’re transforming how companies care for their employees.

Strategic Planning & Execution:
You’ll create and execute a regional sales plan, leveraging your knowledge of the market to drive results. Whether it’s meeting one-on-one with brokers, presenting to groups, or collaborating with internal teams, you thrive in a fast-paced, high-stakes environment.

Collaboration Across Teams:
You’ll work across the organization, closely with Pareto’s account management, underwriting, and marketing teams to deliver tailored solutions, ensuring our stakeholders see the full value of what Pareto offers.

Driving Change:
Every day, you’ll help small and midsize businesses access options once reserved for large firms—offering a path to sustainable, affordable healthcare. You’ll see firsthand how your work drives meaningful results for companies and their employees.

What You Bring

• 5+ years of experience as a top seller of self-insurance, self-funded benefits, stop-loss insurance, or related markets.
• Proven ability to build strong, trust-based relationships with insurance brokers and employee benefits consultants.
• Exceptional presentation, negotiation, and communication skills. You know how to command a room and inspire action.
• Strong familiarity with Salesforce or other CRM tools to track progress and drive results.
• A self-starter mindset with a strong desire and track record of winning and exceeding sales targets.
• Bachelor’s degree preferred.
• Must be currently based in Chicago with the ability often (50%) to travel locally.

What’s in It for You

• Competitive base salary with a performance-based compensation structure.
• Comprehensive benefits, including 100% employer-paid medical coverage, dental, vision, STD/LTD, and a robust 401(k) employer contribution.
• The opportunity to be part of something bigger: a team united in the drive to transform employee health benefits for the greater good.
• A dynamic, growth-focused culture where your contributions are recognized, and your impact is tangible.

Why Pareto?

At Pareto, we “see the field”—we anticipate what’s next and act with intention. We “get it done and get it done right”—delivering exceptional work at a pace unmatched in the industry with strong ‘fire in the belly”. And above all, we’re “in this for the greater good.”

If you’re ready to be on the right side of the fight—to help businesses, take control of their health benefits, lift their people, and drive meaningful change—we want you on our team.

Join us on the ‘right side of the fight.’