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Director, Digital Health Strategy & Operations

United States

About Health-E Commerce: 

Here at Health-E Commerce, we are a consumer health and wellness advocate and online retailer headquartered in New York, NY. Since 2010, we have launched direct-to-consumer e-commerce brands aimed at simplifying the U.S. tax-free healthcare market and helping everyday Americans and companies benefit better from workplace benefits, wellness and health spending programs. 

Our portfolio consists of four brands — FSA Store, HSA Store, WellDeserved Health and Caring Mill.  Health-e Commerce is an HIG Capital portfolio company.  HIG is a leading investment firm with ~$64 billion in AUM and over 125 active portfolio companies. 

About the Role:  

Health-E Commerce is expanding its portfolio of services and entering new product categories that require sophisticated operational, technical, and regulatory workflows. This role supports the Commercial and P&L strategy led by the Chief Digital Health Officer, ensuring operational execution aligns with business goals. The Director, Digital Health Strategy & Operations will serve as the senior operator responsible for designing the operational model, creating cross-functional alignment, and establishing governance for new service offerings.

Specific responsibilities:

Strategy and Roadmap 

  • Develop and maintain the operational roadmap for new services and category expansion.
  • Translate business goals into structured workstreams with clear milestones and accountability.
  • Prioritize initiatives and manage sequencing across internal and external dependencies.

Operational Governance & Cross-Functional Leadership

  • Establish and maintain governance structures for new initiatives
  • Align cross-functional teams around operational objectives, requirements, and timelines.
  • Evaluate tradeoffs, recommend solutions, and resolve cross-functional conflicts to maintain momentum.

Partner & Vendor Management

  • Serve as the primary operational owner for external partners
  • Define SLAs, create governance cadences, and review partner performance metrics.
  • Oversee integrations, operational readiness, and issue escalation for partner workflows.

Business Operations & Performance Management

  • Define KPIs across customer flows, partner performance, fulfillment cycles, and service throughput.
  • Partner with Data to build dashboards and reporting tools that support visibility and decision-making.
  • Provide inputs to financial modeling, forecasting, and operational planning.
  • Regulatory & Compliance Alignment
  • Collaborate with Compliance and Legal to ensure workflows, content, and partner processes meet regulatory and eligibility requirements.
  • Establish processes that maintain customer trust, accuracy, and compliance across experiences.

What you’ll need:

  • BA, MBA Preferred, with strong foundational background in strategic operations, analytical thinking, and cross-functional leadership.
  • Minimum of 5–9+ years of experience in strategy, operations, DTC or e-commerce operations, or complex program leadership.
  • Demonstrated experience structuring and driving multi-stakeholder initiatives across Product, Engineering, Marketing, Data, and Operations.  Digital health experience a must.
  • Strong operational design instincts — able to create governance, sequencing, decision frameworks, and clarity across teams.
  • Excellent communication and executive presence; able to translate business goals into structured operating plans.
  • Experience managing external vendors, service providers, or partnerships with operational dependencies.
  • Ability to bring structure to ambiguity, lead through influence, and make decisions in fast-moving environments.
  • Highly analytical mindset with comfort using data to guide decisions, evaluate tradeoffs, and track performance.

Compensation, Benefits, & Additional Details:

At Health-E Commerce, our goal is to provide an offer that supports growth potential within the role and allows for future salary progression.  Final compensation is evaluated on various factors which include but aren’t limited to experience, skills, internal equity among peers, and geographic location. 

  • Compensation: $140,000 - $180,000
  • Discretionary Annual Bonus Eligibility: Up to 20%
  • Medical, Dental, Vision, and 401K with a company match
  • Dependent Care, FSA & HSA accounts
  • Paid Parental & Bonding Leave
  • Flexible PTO & office closure on all major holidays
  • Monthly wellness & internet reimbursements
  • Professional development including certification support & leadership coaching
  • Mental Health resources
  • 100% remote within the United States
  • Must be able to work EST hours

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