Director, Legal Counsel

Insomnia Cookies is growing fast across the U.S., Canada, and the U.K., and we’re expanding our in-house legal team to support that growth. Reporting directly to the Chief Legal Officer, the Director, Legal Counsel will serve as a trusted business partner to leaders across the organization (including Operations, People, Growth, Marketing, Finance, Supply Chain, and Digital).

This is a full-time, on-site role based out of our NYC office with occasional travel to our Philadelphia HQ. The Director will blend hands-on transactional work with cross-functional strategic counseling, helping shape the next phase of Insomnia’s expansion while building scalable legal frameworks for a high-growth, culture-driven company.

Sweet Position Perks:

• We operate on a 4-day work week, with Fridays as a flex day. While not a standard workday, employees should remain accessible for urgent or time-sensitive needs as our bakeries operate through the weekend. 

• A competitive base salary plus annual bonus compensation package

• Eligibility for our Long-Term Incentive Program

• Excellent comprehensive benefits coverage that includes medical, dental, vision & pet insurance plans

• 401K with contribution match

• 3 weeks paid vacation plus 2 paid Insomnia personal wellness days

• Relaxed, fun, come as you are office culture

• Free cookies, branded swag and so much more!

Key Responsibilities:

•Lead and oversee contract management for the company, including drafting, negotiating, interpreting, and maintaining a wide range of commercial agreements (e.g., leases, supply, manufacturing, vendor, marketing, technology, and service contracts).

•Provide clear, practical, and business-oriented guidance on contract terms, risk allocation, compliance obligations, and dispute resolution.

•Partner with the People Team on employment law compliance, policies, and employee relations, while serving as a trusted advisor to other business functions (including Operations, Growth, Marketing, Finance, and Digital) on a wide range of commercial and strategic matters.

•Partner with outside counsel on litigation, employment, intellectual property, and regulatory issues.

•Assist in overseeing the company’s trademark portfolio and related brand protection initiatives.

•Conduct and supervise legal research and analysis to advise on laws, regulations, and policies affecting the company’s operations, products, and growth.

•Proactively identify, assess, and mitigate legal and regulatory risks across business initiatives.

•Support the CLO in building scalable templates, processes, and playbooks that enable business speed while maintaining compliance and managing risk.

•Review marketing, digital, and employment materials for legal and regulatory compliance.

•Assist with management of disputes, pre-litigation matters, and agency investigations as needed.

•Manage or support special projects as business priorities evolve.

Qualifications:

•J.D. from an accredited law school; licensed and in good standing in at least one U.S. jurisdiction (Pennsylvania preferred or ability to become licensed in PA).

•6–10 years of relevant legal experience, with prior in-house experience preferred (consumer, retail, or growth-stage company experience a plus).

•Substantial experience drafting, negotiating, and managing complex commercial contracts; familiarity with commercial leases is a plus but not required.

•Strong judgment, pragmatic risk tolerance, and the ability to translate legal concepts into actionable business advice.

•Excellent interpersonal and communication skills; proven ability to influence and build relationships across all levels of the organization.

•High integrity, adaptability, and comfort operating in a fast-paced, entrepreneurial environment.

•Creative, resourceful, and self-motivated, with the ability to manage multiple priorities independently.

About us:

Insomnia Cookies was founded in a college dorm room by then-student, Seth Berkowitz. Fast forward 20 years and so... many....cookies... later, our innovative bakery + delivery concept has become a cult brand known for its rabid following of cookie lovers who crave Insomnia’s warm, delicious delivery all day and late into the night. With an expanding footprint of over 300 stores globally, an experiential, “sweet-easy” concept as the brand’s flagship in Philadelphia, Pa. (where Insomnia Cookies is headquartered), and a rapidly-growing nationwide shipping and gifting portfolio... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What’s Possible"!