Cherylyn Harley LeBon is a highly regarded lawyer, advocate, and strategist with over 25 years of leadership experience in Washington, D.C., and abroad. She focuses her practice on government contracts and corporate matters.

With a distinguished background as a Presidential appointee at the U.S. Small Business Administration (SBA) and U.S. Department of Veterans Affairs (VA), Cherylyn leads clients through every stage of the federal procurement process. Her experience is aligned with the SBA’s portfolio, including bank loans, financial assistance, disaster response, and government contracting for 8(a), SDVOSB, WOSB, and HUB Zone firms.

Cherylyn draws on her extensive government experience to advise clients on a broad range of government contracting matters, including regulatory compliance with the agency’s various programs, structuring joint venture agreements, counseling on the Mentor-Protégé program, teaming agreements, contract interpretation and performance counseling, negotiation of Requests for Equitable Adjustment, resolution of subcontractor disputes, contract terminations, suspension and debarment, and advising on small business procurement programs in various federal agencies.

In addition, Cherylyn advises clients on a range of corporate matters, including complex contracts, mergers and acquisitions, banking representations, employment policies, and corporate governance. 

She is committed to helping her clients develop creative and workable solutions to a broad range of matters while enabling them to achieve their financial and corporate goals.

Prior to private practice, Cherylyn was President and CEO of her consulting firm, KLAR Strategies, providing business strategy and guidance to clients, including mid-size companies, technology firms, and boards. Previously, Cherylyn was Senior Counsel for the U. S. Senate Judiciary Committee and was responsible for judicial nominations, civil and human rights, and Congressional oversight of the U.S. Department of Justice. 

Earlier in her career, Cherylyn spent several years working overseas as a finance and telecommunications advisor to the German Bundestag (Congress) and as an international transaction specialist with the Mannesmann Corporation in Dusseldorf, where she structured and negotiated financial transactions in Eastern Europe and Asia. She also served as a media advisor to a Prime Minister candidate in the United Kingdom.

Civic & Professional Engagement

  • Copart, Inc., Independent Board Member – Nominating and Governance and Compensation Committee (2021-Present)
  • SCORE Association, Board Member – Government Relations and Audit Committee (2019-Present)
  • Visit Fairfax (Fairfax County, Virginia), Board of Directors, Chairman (2023-2024), Vice Chair (2022-2023), Treasurer (2021-2022), Secretary (2020-2021), and Board Member (2019-Present)
  • Tower Club (Invited Clubs Network), Member, Board of Governors (2021-Present)
  • Capital Business Development Association (CBDA), Board Member (2023-Present)
  • The University of Kansas, Institute for Leadership Studies, Adjunct Faculty (2021-Present)

Government Experience

  • U.S. Small Business Administration (Presidential Appointee), Assistant Administrator for Intergovernmental Affairs, Deputy Chief of Staff, and Deputy Assistant Administrator, Field Operations (2007-2009)
  • U.S. Department of Veterans Affairs (Presidential Appointee), Congressional and Legislative Affairs Liaison (2006-2007)
  • U.S. Senate Judiciary Committee, Senior Counsel (2003-2005)
  • U.S. House of Representatives, Legislative Aide and Counsel (1993-1995)

Thought Leadership

  • Panelist, GovConnects BizBreakfast: Part of the "Coffee & Capture Strategies" Series, October 17, 2023
  • “Leading Your Business in 2021: What You Need to Know, Now,” Client Alert (Dunlap Bennett & Ludwig), February 15, 2021
  • “Lending A (Business) Hand This Veterans Day,” Client Alert (Dunlap Bennett & Ludwig), November 11, 2020
  • “How Small Businesses Can Survive and Thrive in Our New Economy,” Client Alert (Dunlap Bennett & Ludwig), November 2, 2020
  • “The Paycheck Protection Program Flexibility Act,” Client Alert (Dunlap Bennett & Ludwig), June 18, 2020
  • “Cares 2.0: A Welcome Second Wave of Relief for Small Businesses,” Client Alert (Dunlap Bennett & Ludwig), April 24, 2020
  • “Top 10 Things Small Businesses Need to Know About the Paycheck Protection Program,” Client Alert (Dunlap Bennett & Ludwig), April 10, 2020


  • German
  • Spanish