CMS Leadership

Office of Strategic Operations & Regulatory Affairs

Kathleen Cantwell


Kathleen Cantwell is Director of the Office of Strategic Operations and Regulatory Affairs (OSORA). Kathleen provides leadership and advocacy on behalf of senior CMS/HHS officials regarding policy and regulatory matters. She manages CMS's decision-making process involving the resolution of complex policy issues and critical CMS systems including the development, clearance and publication of regulations, issuances, executive correspondence, Freedom of Information Act requests, responses to Office of Inspector General and Government Accountability Office reports, Federal Advisory Committees and reports to Congress. She also provides management and administrative support to the Office of the Attorney Advisor.

Kathleen previously served within HHS in the Executive Secretariat Office of the Office of the Secretary from 2006 – 2012.  In her capacity as the CMS Team Leader/Senior Policy Coordinator, Kathleen advised the Executive Secretary and other senior Departmental officials on significant CMS policy matters, including key Affordable Care Act decisions and regulatory documents.  From 2000 – 2006, Kathleen served as the Director of Federal Legislative Affairs and Government Affairs Counsel at a national pharmacists association, where she worked as a liaison to Congress during the passage and implementation of the Medicare Part D benefit.  Kathleen earned a BS from Union College in Schenectady, New York and a JD from the Washington College of Law at American University.


Olen Clybourn

Deputy Director

Olen Clybourn is the Deputy Director of the Office of Strategic Operations and Regulatory Affairs (OSORA). Olen works with the Director to provide leadership and overall management of the various support programs such as human resources, budget, contracts, administrative programs and information technology issues. Prior to being appointed as the Deputy, he performed as the acting Deputy Director while maintaining his position as the Director of the Issuances and Records Management Group, where he was responsible for the day-to-day management of the Agency's official policy and guidance process and records management program

He joined CMS after serving 25 years in the United States Air Force and spent his last seven years of his Air Force career at the Pentagon, Washington, DC. From August 1998 to June 2002, he was the Superintendent, Operations Support Division for the Office of the Assistant Secretary of the Air Force for Acquisition and oversaw the management of executive support, correspondence, information management, publications management, human resources and operational support programs. He also co-chaired the administrative process design team for the Secretary and Chief of Staff of the Air Force and led the complete business process reengineering effort for the administrative workflow process for Headquarters Air Force. In February 1996 to August 1998, he was the Executive Manager, Information Systems for the Office of the Chairman of the Joint Chiefs of Staff, Operations Directorate, where he managed an array of operational issues ranging from unclassified to classified. He also was responsible for all day-to-day administrative programs and information management activities.

Olen received a MS Degree in Quality Systems Management from the National Graduate School and a BA Degree in Business Administration where he specialized in Health Services Administration from Saint Leo University.

Page Last Modified:
02/26/2020 08:07 AM