Regional VP Of Sales

Regional VP Of Sales

This is a senior commercial leadership role responsible for driving regional growth and expanding market presence within the complex self-funded healthcare ecosystem. You will lead strategic sales execution across a defined territory, building strong relationships with employer clients, brokers, consultants, and key industry partners. Operating in a highly consultative and solution-oriented environment, you will translate market needs into compelling value propositions that differentiate innovative healthcare navigation solutions. This role combines strategic leadership with hands-on execution, requiring strong pipeline management, forecasting accuracy, and deal oversight. You will also play a key role in developing high-performing sales talent and ensuring consistent revenue performance across the region. This is a high-impact position for a commercially driven leader passionate about transforming healthcare access and affordability.

Accountabilities:

• Develop and execute a regional sales strategy to drive membership growth and revenue expansion across the assigned territory.
• Build and maintain strong relationships with employers, consultants, brokers, and strategic partners to generate and advance pipeline opportunities.
• Lead consultative sales engagements, identifying client challenges and delivering tailored value propositions aligned with market needs.
• Manage complex, multi-stakeholder sales cycles including RFP processes, negotiations, forecasting, and deal execution.
• Ensure disciplined pipeline management and forecasting accuracy using CRM tools such as Salesforce.
• Collaborate with internal teams and external partners, including claims administrators and consultants, to support deal progression.
• Recruit, develop, and lead regional sales talent to consistently achieve or exceed performance targets.

Requirements:

The ideal candidate brings 10+ years of progressive sales experience within healthcare, insurance, or employee benefits industries, including proven success leading regional or distributed sales teams. You have a strong understanding of the self-funded employer healthcare market and a consultative sales approach focused on value creation. A demonstrated track record of consistently exceeding revenue targets and driving new business growth is essential. You possess strong executive presence, along with excellent communication, negotiation, and presentation skills. Experience managing complex sales cycles with multiple stakeholders is required, as well as proficiency in CRM systems such as Salesforce and Microsoft Office tools. You are highly accountable, data-driven, and able to forecast accurately while maintaining strong pipeline discipline. A Bachelor's degree is required, and the ability to travel extensively within the region (20–45%) is expected.

Benefits:

• Competitive base salary with performance-based incentive compensation
• Comprehensive healthcare coverage including medical, dental, and vision
• Life insurance, legal and identity protection, and additional wellbeing services
• 401(k) plan with employer match and immediate vesting
• Generous PTO, paid holidays, parental leave, volunteer days, and sabbaticals
• Tuition reimbursement, certifications support, and leadership development programs
• Strong culture focused on inclusion, recognition, and employee wellbeing
• Additional perks including wellness programs, fitness facilities, and workplace amenities (where applicable)