Naomi May

Naomi advises companies and organizations that deliver educational products and services at all stages of learning, from early childhood education to workforce development. Innovators, investors and operators in the space – whether early-stage edtech companies or established university leaders – rely on her for practical, business-minded counsel to help them navigate a complex regulatory environment. Naomi collaborates with colleagues throughout the Cooley platform to provide industry-informed strategic commercial and product counseling, compliance assessments, targeted advice in administrative actions and litigation, and leadership in complex transactions.

Naomi’s work is energized by deep engagement outside the firm in the nationwide edtech community and within Cooley through relationships across offices and leadership in affinity groups. She is a frequent speaker during edtech events, at higher education conferences, and on firmwide panels. In 2025, Naomi was named Cooley’s Leadership Council for Legal Diversity Fellow.

Naomi joined Cooley in 2013, bringing her experience at public and private schools, as well as in the Office of the General Counsel at the US Department of Education, where she assisted with litigation, rulemaking processes and program services related to Title IV federal student aid. During and before law school, she leveraged her passion for translating between the legal, academic and business worlds to guide colleges and universities through accreditation processes. While focusing on higher education law at the College of William & Mary, Naomi also advised on governance matters, torts, compliance with state and local regulations, student learning assessment and data reporting.

Naomi’s representative experience includes:

Strategic counseling in connection with go-to-market efforts, product and program launches, and commercial agreements

• Advising clients on the impact of federal, state and local education laws on product features, growth initiatives, innovative pedagogies and developing technologies, including generative artificial intelligence
• Developing creative, market-informed product strategies and contracting approaches for clients in areas such as scrutiny of curricular content under shifting state and federal interpretations of nondiscrimination laws and compliance with the patchwork of state and federal children’s data privacy and student data privacy laws including the Children’s Online Privacy Protection Act (COPPA) and Family Educational Rights and Privacy Act (FERPA)
• Staying on the forefront of new funding sources for client initiatives, like apprenticeships and on-the-job employee training, upskilling and educational benefit programs

Compliance counseling and regulatory analyses of operations

• Monitoring the changing regulatory landscape and government enforcement priorities that impact clients in the education ecosystem, whether federal rulemaking processes or agency audits
• Providing clients with nuanced risk management strategies in highly regulated contexts, such as those involving incentive compensation or third-party servicer obligations in connection with services to schools participating in the Title IV federal student aid programs
• Helping clients chart a path forward through the complex, overlapping requirements of the postsecondary “triad” agencies (state educational authorities, accreditors and various federal agencies, including the Department of Education)

Subject matter resource for internal investigations, administrative actions and litigation

• Providing support for litigation and investigative matters involving laws governing education and edtech client activities, ranging from academic program requirements to children’s and students’ data privacy in the school setting
• Representing institutional clients facing investigations and enforcement actions brought by accrediting agencies and other governmental authorities

Deal support and leadership in complex higher education transactions

• Delivering sophisticated guidance through the multilayered negotiation and consents processes involved in college and university M&A
• Partnering with firm deal teams to bring industry-specific insights to inform diligence and strategy