About Leap

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.

About the Role

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 Responsibilities

Commercial 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

Qualifications

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.