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Director of Sales
Healthcare Benefits / Direct Primary Care
Reports To: Chief Revenue Officer
About the Role
We are seeking a Director of Sales to drive regional growth by building strong relationships with employers, benefits brokers, and consultants, and positioning an innovative Direct Primary Care (DPC) model as a core component of modern employee benefits strategies.
This role owns territory performance end-to-end, from pipeline generation through close, and serves as the regional subject matter expert on DPC and value-based primary care. You will play a key role in scaling a differentiated healthcare delivery model that integrates virtual and in-person primary care with wellness, prevention, chronic care management, behavioral health, pediatrics, and acute care.
The ideal candidate thrives in consultative, relationship-driven sales, enjoys building markets, and is motivated by transforming how employers deliver healthcare to their employees.
Key Responsibilities
Territory & Pipeline Development
- Own revenue growth and pipeline generation within an assigned multi-state territory
- Build and maintain strong relationships with employers, benefits brokers, consultants, and advisors
- Serve as the regional subject matter expert for Direct Primary Care and employer-sponsored healthcare solutions
- Establish a scalable, repeatable sales process from prospecting through close
- Define territory plans, performance metrics, and milestones aligned with company growth objectives
- Forecast deal flow and manage long-cycle, consultative sales opportunities
Sales Execution & Partnerships
- Lead complex, multi-stakeholder sales cycles with mid-market and large employers
- Architect and negotiate strategic partnerships and employer agreements
- Collaborate closely with internal teams including Marketing, Account Management, Finance, and Legal to ensure successful client onboarding and retention
- Partner with Marketing to develop compelling sales messaging, collateral, and market positioning
Market Presence & Field Engagement
- Build an on-the-ground presence through face-to-face meetings with employers and benefits advisors
- Host and attend industry events, CHRO forums, chamber of commerce events, and executive networking functions
- Represent the organization at trade shows and regional healthcare and benefits conferences
- Cultivate a strong professional network to drive referrals and market awareness
Qualifications
- 3+ years of B2B sales experience, including at least 2 years selling to organizations with 250+ employees
- 2+ years of experience in employee benefits, healthcare, or related consultative sales
- Working knowledge of Direct Primary Care, value-based care, or employer-sponsored healthcare models strongly preferred
- Proven ability to manage long, complex sales cycles (6+ months) from sourcing to close
- Demonstrated success consistently meeting or exceeding revenue quotas
- Experience building and maintaining relationships with benefits brokers, consultants, and employer decision-makers
- Strong forecasting, pipeline management, and CRM discipline
- Excellent communication, negotiation, and executive-level presentation skills
The Ideal Candidate
- Is passionate about improving access, affordability, and quality in healthcare
- Is a strong storyteller who can clearly articulate a complex value proposition to employers and advisors
- Is highly results-driven, competitive, and motivated by building new markets
- Enjoys being in the field and developing deep professional networks
- Brings a strategic, consultative mindset to selling into HR, Finance, and C-suite stakeholders
- Operates with urgency, ownership, and a growth-oriented mentality
Compensation & Benefits
- Competitive base salary with uncapped commission
- Comprehensive medical, dental, and vision coverage
- 401(k) with company match
- Generous paid time off
- Additional wellness and healthcare benefits
