Senior Director, Commercial Counsel

Leap

About The Position

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.

Requirements

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

Nice To Haves

Exposure to AI regulations and legal AI tooling
Experience managing outside counsel budgets and relationships
Background at an employer benefits or specialty pharmacy company

Responsibilities

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
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
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
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