Director of Legal @ Insomnia Cookies

Delivering Warm Moments, One Cookie at a Time

Reimagining Late-Night Bakery and Delivery for a Global Community

Insomnia Cookies is seeking a Director, Legal Counsel to join its expanding in-house legal team and support the company's rapid growth across the U.S., Canada, and the U.K. Reporting directly to the Chief Legal Officer, this senior leader will serve as a trusted advisor to business partners across Operations, People, Growth, Marketing, Finance, Supply Chain, and Digital.

The Director, Legal Counsel will blend hands-on transactional work with cross-functional strategic counseling, shaping the next phase of Insomnia's expansion while building scalable legal frameworks for a high-growth, culture-driven company. Key responsibilities include leading contract management, providing practical guidance on risk and compliance, partnering with the People Team on employment law matters, and supporting brand protection initiatives. The role also involves collaborating with outside counsel, conducting legal research, and proactively identifying and mitigating legal and regulatory risks.

Ideal candidates will have a J.D. from an accredited law school, 6–10 years of relevant legal experience (with prior in-house experience preferred), and a strong background in drafting and negotiating complex commercial contracts. The ability to translate legal concepts into actionable business advice, excellent communication skills, and comfort operating in a fast-paced, entrepreneurial environment are essential.

Insomnia Cookies, founded in a college dorm room, has grown into a cult brand with over 300 stores globally, a flagship experiential location in Philadelphia, and a rapidly expanding shipping and gifting portfolio. The company continues to revolutionize the cookie experience by imagining what's possible.