[Hiring] VP of Enterprise Sales @Wellnecity

Role Description

We are seeking a VP of Enterprise Sales to drive new business revenue and expand Wellnecity's enterprise client base. This is a hands-on, quota-carrying role responsible for developing relationships, building pipeline, and closing complex enterprise opportunities across the self-funded employer healthcare market. The VP of Enterprise Sales will represent Wellnecity with key clients, advisors, and strategic partners. This role is well suited to an accomplished enterprise seller with an established industry network, a proven track record of closing significant deals, and the ability to generate meaningful early commercial traffic.

This position will report to the Chief Executive Office and be based in Winston-Salem, NC, for in-person meetings as needed. Remote work will be accommodated. The position will be expected to travel periodically for client and firm meetings (<25%). Candidates must be authorized to work in the US without sponsorship.

Key Responsibilities

• Own and achieve individual new business revenue targets through direct enterprise sales.
• Identify, develop, and close new business opportunities with self-insured employers and strategic enterprise clients.
• Build and expand relationships with national and regional benefits consultants, brokers, advisors, and channel partners.
• Lead the full enterprise sales cycle, including prospecting, discovery, solution positioning, executive presentations, negotiations, and contract execution.
• Develop and maintain a strong pipeline of qualified opportunities, with a focus on generating measurable commercial results within the first six months.
• Establish and maintain relationships with senior executive decision-makers, including HR, Benefits, and Finance leaders.
• Partner with executive leadership on enterprise sales strategy, target accounts, market opportunities, and revenue growth priorities.
• Maintain accurate pipeline reporting, forecasting, and CRM activity to support revenue visibility and accountability.
• Collaborate with Marketing, Customer Success, and Product to align sales efforts, support client transitions, and identify growth opportunities.
• Represent Wellnecity at industry events, client meetings, and strategic partner engagements, bringing market and competitive insights back to leadership.

Qualifications

• Bachelor's degree and 10–14 years of relevant experience in health benefit sales, including significant experience selling complex enterprise solutions; Master's degree may substitute for up to 2 years.
• Proven track record of consistently achieving or exceeding individual sales quotas and closing significant enterprise deals.
• Deep knowledge of the self-funded employer healthcare market, including employer buyers, benefits advisors, consultants, and channel partners.
• Established network of relationships with benefits consultants, brokers, or employer decision-makers.
• Demonstrated ability to independently develop pipeline, navigate complex sales cycles, and generate near-term revenue opportunities.
• Strong executive presence, negotiation, relationship-building, and communication skills.

Nice-to-Have Experience

• Experience in healthcare analytics, cost containment, or benefits technology companies.
• Experience in private equity or venture-backed high-growth organizations.
• Experience building channel partnerships at a national level.
• Proficiency with CRM and revenue intelligence tools (e.g., HubSpot, Salesforce, Gong).

Benefits

• 100% employer-paid health insurance for employees and dependents (no waiting period).
• Employer-paid short- and long-term disability.
• Voluntary dental, vision, and life insurance options.
• Voluntary 401(k) with Morgan Stanley platform.
• Flexible paid time off annually, inclusive of holidays.
• Additional wellness and family support programs.
• Benefits offerings may vary by location and employment status.