About LeafLink

LeafLink is the largest unified B2B cannabis platform, providing licensed cannabis businesses a suite of tools to manage their business more effectively, sell or order from their favorite brands and accelerate growth. We are one platform, one solution and we’re defining the way thousands of cannabis brands, distributors, and retailers streamline their operations. With thousands of brands and retailers across 30+ markets in North America, we are setting the industry standard for how cannabis businesses grow together. LeafLink processes more than $5 billion in wholesale cannabis orders annually.

Our team, backed by funding from leading VC's, including Founders Fund, Thrive Capital, Nosara Capital, and Lerer Hippeau is poised to define the cannabis supply chain through technology.  LeafLink was named one of Inc. 5000’s ‘Top 5000 Fastest-Growing Private Companies’; one of Fast Company's 'Top 10 Most Innovative Companies in Enterprise for 2020', joining the ranks of Amazon, Slack, and VMWare; one of Built In NYC's 'Best Places to Work in 2021'; 2024 Fast Company’s Best WorkPlaces for Innovators for Banking, Finance, and Fintech category; 2024 Green Market Report Award for Best Fintech in cannabis - and we're just getting started!

LeafLink is seeking a business-minded and pragmatic Head of Legal to help lead the company’s legal and compliance function during a critical stage of growth. This role will report to the CEO and work closely with the executive leadership team across product, engineering, finance, operations, and go-to-market teams.

The Head of Legal will play a central role in supporting the company’s strategic initiatives, advising on regulatory matters, managing commercial relationships, mitigating risks, and providing insight on all contracts and other legal matters. This position requires a hands-on attorney who is comfortable operating in a fast-paced environment, balancing risk management with practical business solutions, and contributing as both a lawyer and strategic partner.

The ideal candidate is an organized self-starter who enjoys solving complex problems in highly regulated industries and can contribute both as a lawyer and a businessperson to LeafLink’s growth. 

• Serve as a strategic legal partner to leadership across the company on commercial, regulatory, and operational matters
• Draft, review, negotiate, and interpret a wide range of commercial agreements, including customer order forms, SaaS agreements, fintech services, technology partnerships, and data licensing agreements
• Support strategic initiatives including partnerships, corporate development opportunities, and new product launches
• Work with outside regulatory counsel to help navigate evolving regulatory frameworks and support the company’s compliance obligations
• Provide practical legal guidance across a range of areas including commercial transactions, regulatory matters, product development, privacy, employment, and corporate governance
• Maintain and improve standard contract templates, policies, and legal workflows
• Support board and investor governance matters, including preparation of board materials and minutes
• Manage and mentor a small legal team (currently two team members) and coordinate work with outside counsel

• You work collaboratively and maintain excellent customer service
• You have the ability to work quickly and independently in a dynamic, fast-paced environment
• You have significant experience in drafting, negotiating and interpreting commercial and transaction agreements relating to SaaS, FinTech products and services, master services, data licensing, technology, and general commercial transactions
• You have broad legal knowledge that enables you to spot and resolve a variety of legal issues in upcoming product offerings (e.g., regulatory, contract, IP, privacy, consumer protection, risk); and an ability to identify and clearly communicate practical, risk-based solutions
• You show curiosity and a willingness to roll up your sleeves and get into the details of novel and complex business models.

• J.D. from an accredited law school and active membership in good standing with a U.S. state bar.
• 5–8 years of legal experience, including a combination of top-tier law firm and in-house experience.
• Strong experience drafting and negotiating complex commercial agreements.
• Experience advising companies operating in regulated industries, fintech, payments, SaaS, or technology businesses is strongly preferred.
• New York or California Bar membership

• Flexible PTO - you’re going to be working hard so enjoy time off with no cap!
• A robust stock option plan to give our employees a direct stake in LeafLink’s success
• 5 Days of Volunteer Time Off (VTO) - giving back is important to us and we want our employees to prioritize cultivating a better community
• Competitive compensation and 401k match
• Comprehensive health coverage (medical, dental, vision)
• Commuter Benefits through our Flexible Spending Account

Base salary range

$185,000—$245,000 USD