Regional Vice President, Sales - Chicago

ParetoHealth; United States; Remote; USD 100,000 - 125,000; Full time

Job summary

A growing health benefits firm is seeking a Regional Vice President of Sales to drive relationships with insurance brokers in the Chicago territory. The ideal candidate has over 5 years of successful sales experience in self-insurance. This is a remote position with competitive compensation and benefits, including generous PTO and health insurance coverage.

Benefits

Competitive base + incentive pay

100% employer paid insurance benefits

Flexible PTO

Generous 401(K) contribution

Fitness reimbursement

$1,000 annual donation matches

Qualifications

• 5+ years of experience in self-insurance or related markets.
• Proven ability to build trust-based relationships with brokers.
• Exceptional presentation and communication skills.

Responsibilities

• Develop strong relationships with insurance brokers.
• Create sales strategies for the Chicago territory.
• Collaborate with internal teams for tailored solutions.
• Manage local travel to meet with stakeholders.

Skills

Relationship building

Sales strategy execution

Negotiation skills

Data analysis

Consultative selling

Education

Bachelor's degree in business or finance

Tools

Salesforce

Job description

Regional Vice President, Sales - Chicago

Remote

We’re in this for the greater good at ParetoHealth. Our mission is collective greatness, nothing less will do. Our team is a single force united in the drive to transform employee health benefits.

The company was founded in 2011 to help small and medium-sized businesses fight the rising cost of employee health benefits. We blazed the trail with financing innovations that reduce the risks in self-insurance and deliver significant savings—and we continue to lead with a growing ecosystem of partners and world-class cost control solutions.

But success is measured by more than dollars alone and we measure ours by the good that comes from knowing that every client and all their employees can count on effective, affordable healthcare for years to come.

Disclaimer: ParetoHealth does not provide employment visa sponsorship for this position. Candidates must be authorized to work in the United States without sponsorship both now or in the future.

Who We Want:

As a Regional Vice President of Sales (RVP), you’ll be a key force driving our mission forward. Reporting to our SVP, Sales, 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 Chicago 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.

What You’ll Do:

• Build 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.
• Create 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.
• Collaborate 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.
• Drive 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 consistent top seller of self-insurance, self-funded benefits, stop-loss insurance, alternative funding 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 a track record of winning and exceeding sales targets.
• Ability to quickly translate data sets into clear insights that drive decisions and strong results
• Strong broker network and consultative selling skills
• Strong business development and relationship management skills
• Bachelor’s degree in business, finance or related field.
• Must be able to travel at least 50% within territory and some limited travel domestically for Pareto events

What We Offer:

• Competitive base + incentive pay package
• 100% employer paid medical, dental, vision disability and life insurance benefits
• Flexible PTO
• Generous company 401(K) contribution
• Fitness reimbursement
• $1,000 per year donation matches to qualified agencies
• Being part of a fast growing, mission centered team
• An opportunity to be on the right side of the fight advancing the insurance industry!

Who Thrives Here:

RVPs who excel at Pareto see this role as a defining chapter of their career. They are leaders with the vision to help fix a broken healthcare system with the skills to build partnerships that matter at the highest level. Mission-driven with the fire in the belly, relentless in their pursuit of growth and impact. For those ready to lead boldly and leave a mark, join us on the right side of the fight!

We are guided by our values:

• Fire in the belly
  The drive to learn, to improve, and to deliver outstanding value everyday.
• See the field
  The ability to see the big picture and prepare to meet tomorrow’s needs.
• Get it done right
  The passion to produce at higher rates and to the highest standards.
• For the greater good
  A united community creating better health benefit solutions for all.

Disclosures: ParetoHealth is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion, gender, gender expression, age, national origin (ancestry), disability, marital status, sexual orientation, or military status, in any of its activities or operations. We are committed to providing an inclusive and welcoming environment for all members of our staff, clients, volunteers, subcontractors, vendors, and clients.