O'Kelly E. McWilliams III is an attorney in Holland & Knight's Washington, D.C., office, where he advises clients on the human capital aspects of corporate transactional matters. Mr. McWilliams is experienced in providing legal counsel that impacts enterprise strategy/operations, corporate transactions, cost reduction, risk mitigation and corporate culture.

Mr. McWilliams' diverse experience working with CEOs, C-suite, boards and leadership teams across companies in the financial services, technology, food service, healthcare, private equity and startup sectors enables him to leverage a broad perspective and provide counsel that strengthens an organization's legal structure and promotes enterprise efficiencies and growth potential.

Adding to his value, Mr. McWilliams has held a number of key leadership roles, including overseeing a $120 million information technology (IT) project as board chair and trustee for a $110 billion public pension plan, starting up and running a new multimillion-dollar law firm office, and investing in high-return on investment (ROI) technology applications to facilitate enterprise efficiencies/growth.

In addition, Mr. McWilliams advises on high-level executive compensation negotiations, conducts compensation audits related to pay disparity issues, and collaborates with senior executives and boards to develop compensation metrics to align management with organizational environmental, social and governance (ESG) goals.

Prior to joining Holland & Knight, Mr. McWilliams was a partner at a large U.S. firm in its Washington, D.C., office.

Representative Experience

  • Advised the audit committee of a publicly traded company and conducted internal investigation based on whistleblower allegations related to a key member of the executive leadership team
  • Advised the board of directors of a large nonprofit and conducted an internal investigation based on allegations from senior management of an inappropriate relationship between the chief executive officer and general counsel and other violations of the conflict of interest policy
  • Advised the administration and compensation committee of a large private company and conducted an investigation based on claims of disparate treatment in compensation and promotions
  • Advised a senior management team related to whistleblower allegations of disparate treatment based on supervision and management practices
  • Advised the board of directors of a high-profile nonprofit and conducted an internal investigation based on suspicions of fraud, abuse and of violation of the organization's conflict of interests, expense and reimbursement policies
  • Advised the board of directors of a publicly traded company and conducted an investigation based on complaints of mismanagement and waste related to internal technology modernization projects

  • Assisted a New York-based investment firm by sourcing and seeking access to additional capital
  • Represented a Chicago-based investment bank and management firm in raising their first fund, in addition to performing work related to bonds and issuances
  • Represented a global investment and advisory firm with $55 billion under management in employment and corporate matters

  • Mitigated whistleblower claims from senior managers of a manufacturer's accounting department based on allegedly fraudulent practices
  • Conducted internal investigation for a financial services client's board of directors of an executive's alleged sexual harassment and conduct of various employees
  • Protected a life sciences company's trade secret and confidential information by pursuing and restricting five top employee's attempt to compete
  • Assisted a Fortune 500 technology company in successfully resolving whistleblower allegations without liability retaliation
  • Proactively avoided liability and risk for violation of federal and state discrimination laws and the Worker Adjustment and Retraining Notification (WARN) Act for an energy company
  • Represented a large not-for-profit organization in connection with the investigation of alleged misconduct by a senior level officer
  • Advised government contractor's mergers and acquisitions (M&A) team on the reality of layoffs that M&As typically produce and the steps to mitigate liability

  • Compiled record of investing in high-return on investment (ROI) technology applications that have facilitated enterprise efficiencies and growth through digitalizing data
  • Advised an emerging technology services company by sourcing and seeding $50 million in capital resources to develop the company's supply chain, and worked with senior executives to align executive compensation with overarching business goals
  • Actively managed a $120 million information technology (IT) project to improve operating efficiencies and minimize cybersecurity risks for the Virginia Retirement System
  • Started up, grew and managed the profit and loss (P&L) for a top 50 law firm in Washington, D.C., Virginia and Maryland providing full legal services across multiple disciplines in one of the country's most competitive markets
  • Collaborated with mergers and acquisitions (M&A) team of a healthcare company to design strategies to meld the two organizations most effectively and efficiently for multiple stakeholders
  • Onboarded and exited several management teams to drive increased profits and performance
  • Led due diligence for a private equity (PE) firm acquiring two portfolio companies in the artificial intelligence (AI) space

  • Provided recommendations to a Fortune 500 engineering company on diversity, equity and inclusion (DE&I) metrics relating to their talent practices to ensure systemwide transformation
  • Established links between environmental, social and governance (ESG) and senior management compensation for several private equity (PE) portfolio companies and incorporated ESG metrics in the due diligence process for a PE fund
  • Advised senior leadership of a Fortune 500 company in creating a more inclusive workplace culture by revamping their hiring, promotion and compensation strategies as well as auditing various departments and company processes to attract and retain top talent
  • Negotiated the equity award granted to a wholesale retailer's chief executive officer (CEO), including drafting and negotiating a restricted stock award, a nonqualified option award and a profit interest award
  • Structured and implemented an innovative management incentive plan for an international manufacturer
  • Advised the senior management team of a marketing information services company in negotiating their employment and equity arrangements in connection with a private equity firm's acquisition
  • Led workforce analysis for a consumer products company with recommendations on policies/practices to fill future workforce gaps, transfer knowledge through succession and move skill base to new technologies
  • Collaborated with an energy company to increase incentives and link compensation to accurate performance metrics to ensure that new hires were not blocking the advancement of critical internal talent
  • Represented a public staffing company in adoption and documentation of profits interest plan and change of control arrangements


  • George Mason University School of Law, J.D.
  • Longwood University, B.B.A., Banking, Corporate Finance and Securities Law
Bar Admissions/Licenses
  • District of Columbia
  • Maryland
  • Virginia
  • Virginia Retirement System (VRS), Board of Trustees, 2017-2022 Chair, 2020-2022
  • Kappa Alpha Psi Foundation, General Counsel, 2019-Present
  • Virginia Bar Association, Judicial Screening – Federal Judgeships, 2010-2015
  • Epsilon Zeta Boule Foundation, Chairman, 2016-2018
Honors & Awards
  • Best Lawyers in America guide, Litigation – Labor and Employment, 2017-2022
  • Washington, D.C. Super Lawyers magazine, Employment & Labor; Employment Litigation: Defense; Business/Corporate, 2014-2021
  • The Legal 500 USA, Employment: Employee Benefits and Retirement Plans (Design), 2019

Speaking Engagements