Leap is one of the fastest-growing benefits solutions and a category-defining pioneer in employer specialty pharmacy. We are reshaping how life-changing therapies are delivered and financed, ensuring patients get the treatment they need while employers finally get a fair deal.
Specialty drugs and infusions represent nearly 10% of all healthcare spend and are the fastest-growing cost category for employers. Leap tackles this challenge with a novel approach: eliminating hidden markups, expanding access to high-quality infusion providers, and bringing clarity and fairness to how therapies are priced and paid for.
We’re proud to partner with numerous Fortune 500 companies and leading TPAs. Each patient we serve creates immediate ROI: lower costs, improved access, and better care. Join us as we redefine what’s possible in specialty care.
The Senior Director, Commercial Counsel is Leap's day-to-day legal operator — the person who keeps our commercial engine running as we scale. This role owns the full lifecycle of commercial contracting across our employer and TPA client base, vendor relationships, and operational legal needs, partnering closely with Sales, Marketing, Client Success, Finance, and Operations, and HR to enable fast, compliant deal-making. You will build and own the systems, templates, and processes that allow a lean team to move with speed and precision, while serving as a trusted advisor who supports the needs of the business. This position reports to the General Counsel.
Key ResponsibilitiesCommercial Contracting
Own end-to-end negotiation and execution of MSAs, CDAs/NDAs, BAAs, vendor agreements, consulting agreements, and amendments with self-funded employer clients and TPAs
Maintain and continuously improve a library of contract templates and playbooks that enable the business to move faster with less back-and-forth
Manage and administer Leap's contract management system, ensuring visibility and accountability across all active agreements
Legal Operations & Compliance
Build scalable contracting and compliance workflows that reduce legal bottlenecks and support a high-growth, lean team
Leverage legal AI tooling and automation to drive efficiency across repeatable legal tasks
Stay current on relevant regulatory frameworks — including HIPAA, ERISA, anti-kickback, FTC, and emerging AI regulations — and translate them into actionable guidance for the business
Cross-Functional Partnership
Serve as the embedded legal partner for Sales and Client Success, supporting deal structuring and accelerating time-to-close on commercial agreements
Support HR with offer letters and standard employment documentation
Draft contest rules and review B2B marketing materials as needed
Organizational & Strategic Support
Manage outside counsel relationships efficiently, with a strong bias toward resolving matters in-house
Identify and take on emerging legal needs as Leap enters new markets, launches new products, or explores new business models
Provide legal support on special projects at the direction of the General Counsel
Required
6+ years of commercial, technology, or healthcare transactional legal experience, with meaningful time at a premier law firm
In-house experience at a health tech, digital health, or employer benefits company — ideally one that has scaled from early stage
Hands-on experience drafting and negotiating a wide range of commercial agreements, including those specific to the self-insured employer and TPA market
Deep working knowledge of HIPAA, ERISA, and related healthcare regulatory frameworks
Demonstrated ability to build legal processes and systems from scratch, including contract management and self-serve tools
JD from an accredited U.S. law school; licensed and in good standing with a state bar
Preferred
Exposure to AI regulations and legal AI tooling
Experience managing outside counsel budgets and relationships
Background at an employer benefits or specialty pharmacy company
At Leap, we’re building an outlier company with real impact — and that takes focus, energy, and commitment. If that excites you, we’d love to hear from you.
Leap is an equal opportunity employer and welcomes applicants from all backgrounds. We’re committed to building a team that reflects a diversity of perspectives, experiences, and identities.
