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Jamie is a senior Government Affairs professional with more than 25 years of experience at the federal and state levels, with significant practice in the areas of issue advocacy, electoral campaigns, tax strategy and grassroots campaigns. He is well known as an expert on real estate, housing finance and insurance-related issues, and brings his wide range of experience to the firm's active Washington, D.C. lobbying practice.

The services Jamie offers to his government relations clients stretch past what other lobbyist firms might typically offer. Jamie assists his clients with reaching their organization's goals by keeping close tabs on their pressing federal issues. For example, he was able to secure much-needed CARES Act funding for a national organization through congressional support, which he developed through a targeted advocacy campaign involving both congressional and grassroots support.

Jamie also assists his clients with a variety of federal tax issues. He continuously educates the policy holders of a specialty real estate organization on potential negative impacts of federal tax proposals. Additionally, he helped an international real estate company successfully stop the passage of transfer tax proposals in multiple locations that would have negatively affected their business. Also for this company, Jamie established a national monitoring service to spot additional locations where similar transfer tax proposals could potentially appear.

Additionally, Jamie acts as the federal lobbyist for one of the largest cities in Ohio. Throughout his tenure for the city, he has successfully secured multiple funding initiatives from recent Appropriations legislation. During the COVID-19 pandemic, Jamie and his team was very active in obtaining information and clarity on funding sources and program requirements, particularly with the U.S. Department of Housing and Urban Development (HUD).

Jamie has a hands-on approach when it comes to client service. He collaborates with others on the Government Relations team to frequently release alerts and blogs on breaking political news and events to keep clients up to date. He checks in with his clients daily and weekly with key developments important to them and is always readily available and exceptionally responsive to requests. His relationships with members at the federal level run deep and are built on years of trust and direct lines of communication. Through these relationships, he is able to push his client's concerns to the forefront.

Jamie is not just a lobbyist; he is well versed in the realm of government affairs, having spent many years performing multiple aspects of the job. Prior to Calfee, he served as Vice President and Deputy Chief Lobbyist for the National Association of Realtors (NAR), the largest trade organization in the United States with 1.4 million members, where he was responsible for managing NAR's Congressional Affairs, Grassroots, Issue Advocacy and Communications staff. In addition, he was heavily involved in setting PAC strategy for the organization. Jamie lobbied senior members of Congress, including leadership on both sides of the political aisle.

During his tenure at NAR, he successfully lobbied on major legislative and regulatory initiatives such as:

  • The Tax Cuts and Jobs Act of 2017
  • Terrorism Risk Insurance Act
  • Passage of the Homebuyer Tax Credit along with two extensions
  • Housing Finance Reform
  • Dodd-Frank Wall Street Reform legislation, including Consumer Financial Protection Bureau
  • Electronic signature legislation
  • Technology issues pertaining to online real estate listings and transactions

Jamie earned his B.A. in Government and Politics from the University of Maryland at College Park. Professional certifications include Realtor Association Certified Executive from the National Association of Realtors, Public Policy Certification from the National Institute for Lobbying and Ethics and the Professional Lobbying Certificate from the Association of Government Relations Professionals.


B.A., University of Maryland at College Park

Realtor Association Certified Executive (RCE) from the National Association of Realtors

Public Policy Certification from the National Institute for Lobbying and Ethics

Professional Lobbying Certificate from the Association of Government Relations Professionals

Jamie Gregory – an employee of Calfee Strategic Solutions, LLC – is not licensed to practice law. 

Professional & Community

Professional & Community

  • University of Maryland Board of Governors Advocacy Committee, Member, 2020-2022
  • University of Maryland Center for American Politics and Citizenship, Advisory Board Member, 2012-2020
  • City of Annapolis Board of Appeals, Past Chairman

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