Head of Sales

Welldoc is at the forefront of digital health, driven by a powerful mission: empowering better cardiometabolic health through AI-powered, personalized digital tech, with a vision to be the leading advanced AI digital technology partner across the healthcare industry. We're a team passionate about leveraging cutting-edge science to improve lives, united by core values of collaborative innovation, accountability to excellence, customer focus, efficiency, and unwavering integrity, quality, and safety.

At Welldoc, you'll thrive in a collaborative and innovative environment where your contributions directly impact our mission. Recognized as a Great Place to Work for the past four years and named to Modern Healthcare’s Best Places to Work 2025, as well as being an industry thought leader featured at SXSW and in the Wall Street Journal and Economist, we invite you to make a real difference in healthcare with us.

Job Purpose

Reporting to the COO, the Head of Sales will design and execute our enterprise sales evolution. You will lead our next chapter of expansion by transforming complex sales cycles into a predictable, repeatable, and high-performing revenue stream.

You will build structure, rigor, and accountability into the sales motion while personally leading large strategic accounts. This is a hands-on executive role requiring deep experience selling complex healthcare solutions with 9–24 month sales cycles.

Candidates commutable to the Columbia, MD area will be expected to follow a hybrid work schedule. 

What You Will Own

Revenue Acceleration & Predictability

• Deliver annual new ARR targets with disciplined forecasting
• Build and sustain a robust sales funnel, maintaining a 3x–4x pipeline coverage model to ensure long-term target attainment and market penetration. Systematically identify and remove friction in the sales process to increase overall win rates and strategically compress complex sales cycles. Champion a "Growth-at-Optimal-Cost" mindset, ensuring that revenue expansion is achieved through sustainable unit economics and efficient resource allocation. Establish quarterly board-ready revenue reporting and strategic insights.

Enterprise Market Expansion

Own strategy and execution across:

• National & regional health plans
• Large PBMs
• ACO’s and Health Systems
• State Entities in support of the Rural Health Transformation Program
• Fortune 1000 self-funded employers
• Consultant-driven employer channels
• Develop segmentation strategy and account prioritization model.

Building a Scalable Sales Engine

This role will be responsible for transforming the current sales function into a world-class, repeatable revenue engine designed for rapid scale:

• Recruit and develop Regional VPs and Enterprise Directors
• Deploy a rigorous, structured sales methodology tailored to the unique complexities of the 9–24 month healthcare sales cycle. Standardize:
  • Qualification criteria
  • Deal desk governance
  • RFP management
  • Pricing discipline

Institute a data-driven management rhythm, including disciplined weekly pipeline reviews and comprehensive Quarterly Business Reviews (QBRs), to ensure total team accountability.

Strategic Deal Leadership

As a hands-on executive, the Head of Sales will bridge the gap between high-level strategy and tactical execution for our most critical accounts:

• Personally lead top 10 strategic enterprise deals
• Architect and negotiate sophisticated value-based and outcomes-oriented contract models that ensure mutual long-term success. Navigate complex sales process including: clinical, actuarial, product development, pharmacy, and procurement stakeholders
  • Translate Welldoc’s complex AI capabilities into clear, compelling narratives aligned with the industry's most pressing clinical and financial priorities including:Medical cost reduction
  • GLP-1 optimization strategy
  • Cardiometabolic risk reduction
  • Quality improvement and Stars/HEDIS impact

Cross-Functional Leadership

Success in this role requires seamless orchestration across the entire organization to ensure Welldoc’s value proposition is backed by operational excellence by partnering closely with:

• Marketing (demand gen & brand credibility)
• Clinical & Outcomes (evidence narrative)
• Product (enterprise requirements)
• Finance (unit economics discipline)
• Customer Success (renewal & expansion)

Required Skills & Experience

• Experience: 12+ years in enterprise healthcare sales
  • 5+ years building and leading high-performing teams
  • Demonstrated experience selling into:
    • Health plans
    • PBMs
    • Large employers
    • ACO’s and Health System’s
  • Experience scaling revenue 50+% YoY
  • Proven success managing 9–24 month enterprise cycles
  • Familiarity with value-based contracting

• Coaching Mindset: skilled in developing sales professionals
• Process-Driven: Exceptional organizational skills with the ability to manage complex RFP processes and security requirements without losing momentum.
• Communication: Masterful presentation and negotiation skills; ability to simplify complex technical or clinical value propositions for executive audiences.
• Adaptability & Maturity: The ability to pivot between high-level strategy and granular operational tasks in a fast-paced, high-growth environment.
• Cross-Functional Collaboration: Ability to partner with Marketing, Clinical, Product, and Finance teams to align the company's value proposition with market needs.

Welldoc operates in ISO 13485 and MDSAP regulated and HITRUST and SOC 2 Type II compliant environments.  Therefore, it is expected that all employees will have either, prior experience working in  those environments or, will be trained to understand the requirements needed to work and support those requirements and culture as they relate to individual roles and responsibilities.

Education                                                     

• Bachelor's degree in business or related field of study. 

Compensation & Benefits

Welldoc offers a competitive compensation package which, in addition to salary, includes generous PTO, medical insurance, dental insurance, vision care, life and disability insurance, retirement benefits. and the opportunity to participate in health savings accounts and/or dependent care accounts.

The anticipated salary range for this position is $200,000-$450,000/year inclusive of base salary and meeting 100% of team sales objectives.

Upon receipt of a conditional offer of employment, you may be required to complete and clear a multi-panel drug screening process.  This screening is in connection with requirements set by certain of the Company’s customers, with which you may be working in this role, and will at all times be administered all applicable laws.