Strategic Enterprise Sales Director

Location: New York Preferred (Flexible)
Territory: Eastern U.S. (Maine through the Carolinas)
Compensation: $200K–$250K Base + Double OTE + Comprehensive Benefits

About the Company

Our client is a market-leading healthcare organization transforming how large employers deliver and manage healthcare for their populations. Through an integrated care model spanning Primary Care, Behavioral Health, Occupational Health, Pharmacy, Wellness, and Virtual Care, they partner with some of the largest and most recognizable employers in the U.S.

With a national footprint serving millions of members, the organization has built long-term client partnerships by helping employers improve health outcomes while achieving meaningful healthcare cost savings.

The Opportunity

Our client is seeking a Strategic Enterprise Sales Director to drive net-new business growth across Fortune 1000 and large self-insured employers throughout the Eastern U.S.

This is a highly consultative, complex enterprise sale with average deal sizes of approximately $2.5M in annual revenue. The ideal candidate has a proven track record of closing large employer healthcare or benefits deals, navigating multiple stakeholders, and leveraging consultant and broker relationships to win business.

What You’ll Do

• Drive new business with Fortune 1000 and large self-insured employers
• Own the full sales cycle from prospecting through close
• Build relationships with senior HR, Benefits, Finance, Operations, and C-suite stakeholders
• Partner with consultants and brokers to generate and accelerate opportunities
• Develop ROI-driven business cases and lead complex sales processes
• Consistently exceed revenue targets and maintain a strong pipeline

What We’re Looking For

• Proven success closing complex enterprise deals into Fortune 1000 organizations
• Experience selling healthcare, employee benefits, navigation, population health, onsite/near-site care, or related solutions
• Track record of closing $1M+ enterprise contracts; multimillion-dollar deal experience preferred
• Strong consultant and broker relationships 
• Experience selling into self-insured employers strongly preferred
• Ability to clearly articulate how you’ve won large, complex sales opportunities

Compensation & Benefits

• $200K–$250K Base Salary
• Double OTE (Uncapped)
• Medical, Dental & Vision Coverage
• 401(k) with Company Match
• Generous PTO & Paid Holidays
• Life & Disability Insurance
• Employee Assistance & Wellness Programs
• Comprehensive Benefits Package