Regional Vice President, Mid Market Sales

For our client, we are seeking a Regional Vice President, Mid Market Sales to join the team of a leader in the Healthcare space.

This leader will own mid-market new-business growth across a defined territory, with a strong focus on selling health and benefits solutions to self-insured employers. The role requires disciplined territory planning, executive-level selling, and close collaboration with external benefits advisors and health plan partners. Success in this position will depend on building a strong pipeline, guiding complex sales conversations, and advancing opportunities from first outreach through signed agreement.

Location:

Remote

Compensation: $263,520 – $299,400 annually

• Own new-business development within your territory, targeting suitable employers for the company's solutions.
• Build and execute a focused territory strategy prioritizing target accounts and growth opportunities.
• Maintain proactive prospecting through direct outreach and partnerships with benefits consultants and health plans.
• Lead thorough discovery to understand employers' benefits strategies and desired outcomes.
• Own the full sales cycle from prospecting to contract closure, ensuring clear next steps are established.
• Identify and address obstacles to advance opportunities and maintain sales momentum.
• Maintain accurate sales forecasting and CRM records, participating in regular pipeline reviews.

• 5-7 years of experience selling health or benefits solutions to self-insured employers.
• Proven track record of generating qualified leads through proactive outbound prospecting.
• Strong discovery skills to uncover business challenges and clarify priorities.
• Experience navigating complex sales cycles and engaging senior executives.
• Ability to translate insights into tailored recommendations and compelling business cases.
• Experience collaborating with benefits consultants and health plan account managers.
• Bachelor's degree required.

• Competitive salary with generous annual cash bonus
• Equity grants and employee stock purchasing plan (ESPP)
• Remote-first work culture with flexible time off
• Generous parental leave and health, dental, and vision insurance
• 401k retirement savings plan and Lifestyle Spending Account (LSA)
• Mental health support solutions and more.

Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.