Regional Vice President, Mid-Market

A rapidly growing, mission-driven company is seeking a Regional Vice President, Sales - Mid Market to join its dynamic team. This organization is revolutionizing the employee benefits space by simplifying and enhancing the healthcare experience for employers and employees alike. Through a cutting-edge technology platform, they consolidate benefits like telemedicine and mental health services, making them more accessible and cost-effective. With over $100M in fundraising to date and recent Series D funding secured, this company continues its high-growth trajectory. Recognized by Inc.'s Fastest Growing Startups and Built In Chicago’s Best Places to Work, they are expanding their sales team and looking for a top-performing sales leader to drive growth in the mid-market segment. As a Regional VP, Sales - Mid Market, you will play a crucial role in expanding the company’s footprint by building broker relationships, driving sales cycles, and closing new business. You will formulate and execute a strategic plan to maximize sales growth while generating revenue within your assigned region.

• $250,000 - $350,000

Responsibilities:

• Develop and execute a go-to-market strategy to engage and grow broker partnerships.
• Drive sales efforts focused on employer benefits brokers, addressing the unique challenges faced by mid-market employers (100-3K lives).
• Build trust and foster long-term relationships with brokers and internal stakeholders.
• Demonstrate a proactive sales approach by consistently working leads, conducting follow-ups, and closing business.
• Develop a deep understanding of the company’s product offerings and clearly articulate its cost-containment value proposition to brokers and employers.
• Work cross-functionally with Sales, Marketing, Customer Success, and Product teams to drive successful sales outcomes.
• Maintain accurate sales tracking and forecasting using Salesforce.
• Meet or exceed assigned sales objectives, including monthly, quarterly, and annual booking targets.
• Stay adaptable to changes in a fast-paced, high-growth environment.

Required Qualifications:

• 6 years of field sales experience, preferably in employee benefits, HR technology, PEO, healthcare navigation, virtual care services, or healthcare data analytics.
• Proven track record of success in broker channel sales and acquiring new brokerage partnerships.
• Strong experience selling to mid-market employers (100-3K lives) is highly preferred.
• Excellent relationship-building and negotiation skills with the ability to foster long-term partnerships.
• Executive presence with exceptional presentation and communication skills, particularly when engaging C-suite executives.
• Self-starter mentality with a results-driven approach to sales.
• Ability to travel up to 50% of the time, including local meetings and out-of-town travel (2-3 times per month for 2-4 days at a time).

Total Rewards & Benefits

• Medical, Dental, and Vision insurance
• HSA contribution match
• Stock options for eligible roles
• 401k match
• Paid parental leave
• Company-sponsored Short-Term and Long-Term Disability coverage
• Flexible PTO policy

If you meet the required qualifications and are interested in this role, please apply today.

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