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 founders or established university leaders – rely on her for practical, business-minded counsel to help them navigate a complex regulatory environment. Naomi collaborates with colleagues across 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. Her work is energized outside the firm by deep engagement in the nationwide edtech community and within Cooley through diverse relationships and leadership on committees and in affinity groups.

Naomi joined Cooley in 2013, bringing her experience at public and private schools, as well as service 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 law school, she worked in the offices of University Counsel and Institutional Analysis and Effectiveness (now Institutional Accreditation & Effectiveness) at William & Mary, combining her legal training and accreditation background to work on governance issues, torts, compliance with state and local regulations, student learning assessment, and data reporting.

Before law school, Naomi provided private K-12 and higher education institutions with accreditation counseling, development and analysis of customized surveys and inventories, and solutions for integrating strategic planning, budgeting and assessment.

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 contracting approaches for clients in areas such as student data privacy
• Staying on the forefront of new funding sources for client initiatives like apprenticeships and on-the-job employee training/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 client activities, ranging from academic program requirements to children’s data privacy
• Representing institutional clients in government investigations and enforcement actions before accrediting agencies and other educational 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