Michael Gleeson
Rockville
Summary
Accomplished tax policy expert with more than 15 years of experience translating complex federal and state tax laws into clear, actionable guidance. Former IRS Chief Counsel advisor, Congressional tax staffer, and trade association leader. At Tax Analysts, translated daily tax developments for more than 150,000 professionals nationwide. Trusted media voice, mentor, and strategic communicator. Proven success modernizing tax workflows and leading high-performing teams. Holds advanced degrees in taxation and public management; invited lecturer at Johns Hopkins and the University of Galway.
Overview
14
14
years of professional experience
1
1
Certification
Work History
Tax Law Specialist
Internal Revenue Service (IRS), Office of Chief Counsel
06.2024 - Current
- Translated complex federal tax laws and accounting method rules into clear, actionable guidance for IRS attorneys and taxpayers. This significantly improved case resolution timelines and reduced downstream review conflicts by equipping staff with consistent, user-friendly interpretations grounded in legal precedent.
- Fostered development of a six-attorney cohort by designing and leading technical trainings on change in accounting period cases. Mentored staff in navigating nuanced legal frameworks, building confidence and sharpening their ability to deliver timely, accurate advice on high-stakes taxpayer requests.
- Modernized the office’s internal workflows by building a digital precedent database from thousands of historical IRS responses. This innovation decreased legal research time by 40%, improved review consistency, and helped institutionalize critical knowledge that previously resided only in staff memory.
- Collaborated with senior reviewers, front-line attorneys, and policy officials to streamline the review process for accounting method determinations. Delivered faster case turnaround and ensured technical accuracy through targeted process redesign and better knowledge-sharing across functional teams.
Legislative Director, Finance, Administration & Intergovernmental Relations (FAIR)
National League of Cities (NLC)
01.2022 - 05.2024
- Led cross-functional efforts to secure a groundbreaking IRS ruling exempting lead pipe replacement reimbursements from federal tax. This policy shift enabled thousands of cities to accelerate public health improvements and advance infrastructure projects without imposing tax burdens on homeowners.
- Elevated talent and culture by mentoring over two dozen junior staff, fellows, and cross-departmental policy professionals. Helped build long-term organizational capacity in public finance and tax policy through regular coaching, collaborative projects, and individualized development plans.
- Influenced key federal guidance by crafting compelling comment letters and technical memos on municipal finance regulations. Successfully persuaded IRS and Treasury officials to reconsider restrictive interpretations, resulting in expanded flexibility and improved access to federal funding for local governments.
- Communicated complex municipal tax issues to internal teams, external partners, and national media outlets. Delivered targeted, plain-language messaging that clarified federal developments for city leaders, federal partners, and journalists, enhancing NLC’s reputation as a go-to source for tax analysis.
Legislative Manager, Finance, Administration & Int
National League of Cities
02.2020 - 01.2022
- Led development of federal tax and finance policy in partnership with a 50-member advisory committee representing diverse city governments. Facilitated structured working groups that produced consensus recommendations, aligned local priorities with national advocacy goals, and strengthened the organization’s legislative credibility among policymakers and federal agencies.
- Communicated directly with congressional staff, Treasury officials, and mayors to translate complex federal tax regulations into practical guidance for municipalities. Served as a key conduit between federal policy and local implementation, ensuring cities could act quickly on new funding and compliance opportunities.
- Managed cross-functional and fully remote teams during the COVID-19 pandemic, leading legislative staff, committee members in delivering real-time federal tax analysis and member guidance. Maintained high engagement and productivity across geographic distances by instituting structured communication, virtual collaboration tools, and a culture of accountability and responsiveness.
Founder & Principal
Michael Gleeson & Associates
09.2018 - 02.2020
- Results Driven Success. Founded a boutique lobbying firm, providing expert federal tax representation and advocacy services. The firm helped clients navigate complex tax challenges. The firm focused on strategic planning, relationship-building, and delivering results-driven solutions.
- Government Engagement Driving Client Outcomes. Established and maintained meaningful connections with senior government officials at the Department of Treasury, on the House Ways and Means Committee, and on the Senate Finance Committee, to advance client priorities.
Vice President, Special Situations
Height Capital Markets
10.2017 - 08.2018
- Expert Tax Policy Analyst. Authored detailed reports and analyses of the 2017 Tax Cuts and Jobs Act (TCJA) that translated complex tax policies into clear, strategic client publications. In the process, Height became a leader among investors as a go-to firm for key, actionable insights on TCJA.
Director, Government Relations
National Grocers Association
01.2017 - 10.2017
- Advocated for small business tax policy on behalf of over 1,000 independent grocers—core small business operators similar to H&R Block’s clientele. Developed and communicated technical guidance on proposed federal tax changes, helping grocers navigate compliance, manage pass-through taxation, and mitigate risks under emerging IRS interpretations.
- Partnered with industry economists and policy experts to assess how federal tax proposals would impact small business grocers’ bottom lines. Translated complex legislative language into clear, actionable guidance used by business owners and trade press, equipping stakeholders to advocate effectively and comply confidently with shifting tax requirements.
Director, Legislative Affairs
Association of Advanced Life Underwriting (AALU)
04.2016 - 01.2017
- Successful Advocacy for Membership. Led bipartisan lobbying efforts to inform members of the U.S. House of Representatives, Senators, and their staff about the challenges posed by the Camp Draft. My advocacy contributed to ensuring the Camp Draft’s harmful positions towards life insurance were not included in the Tax Cuts and Jobs Act.
- Tax Policy Education Leadership. Co-led initiatives to educate tax and non-tax staff on the complexities of life insurance taxation—techniques that could be replicated for real estate taxation—resulting in increased Congressional understanding and engagement.
Tax Legislative Assistant
Office of Congressman Jim McDermott
09.2013 - 04.2016
- Legislative and Regulatory Leadership. Drafted and secured support for the Student Tax Relief Act of 2015, enabling 50,000 students of Corinthian Colleges to exclude forgiven student loans from taxable income. This provision was later adopted by the Department of Treasury as a Revenue Procedure.
- Bipartisan Legislative Advocacy and Success. Worked across party lines to secure the passage of the State and Local Sales Tax Deduction Fairness Act, successfully collaborating with majority staff while serving in a minority office. Played a key role in advancing this critical tax policy as part of an end-of-year legislative package, delivering important benefits for taxpayers.
Capitol Hill Correspondent
Tax Analysts
05.2011 - 09.2013
- Strong Tax Communications Abilities. Reported on federal tax policy developments; translated complex legislative tax changes for a professional audience of 150,000 tax practitioners.
Education
Master of Arts - Public Management
JOHNS HOPKINS UNIVERSITY, Kreiger School of Arts And Sciences
Washington, DC05.2016
Master of Science - Taxation
AMERICAN UNIVERSITY, Kogod School of Business
Washington, DC12.2015
Certificate - Comparative Tax and Administration
HARVARD UNIVERSITY, Kennedy School of Government
Cambridge, MA08.2014
Bachelor of Arts - Political Science and History
UNIVERSITY OF WASHINGTON
Seattle, WA05.2006
Skills
- Federal & State Tax Law Expertise
- Tax Research & Technical Writing
- Team Leadership & Talent Development
- Legislative & Regulatory Strategy
- Content Strategy & Public Communication
- Cross-Functional Collaboration
- Remote Team Management
- Process Improvement & Innovation
- Client-Facing Support for Tax Professionals
- Stakeholder Engagement & Influence
Certification
- CPA License - In Progress
Timeline
Tax Law Specialist
Internal Revenue Service (IRS), Office of Chief Counsel
06.2024 - Current
Legislative Director, Finance, Administration & Intergovernmental Relations (FAIR)
National League of Cities (NLC)
01.2022 - 05.2024
Legislative Manager, Finance, Administration & Int
National League of Cities
02.2020 - 01.2022
Founder & Principal
Michael Gleeson & Associates
09.2018 - 02.2020
Vice President, Special Situations
Height Capital Markets
10.2017 - 08.2018
Director, Government Relations
National Grocers Association
01.2017 - 10.2017
Director, Legislative Affairs
Association of Advanced Life Underwriting (AALU)
04.2016 - 01.2017
Tax Legislative Assistant
Office of Congressman Jim McDermott
09.2013 - 04.2016
Capitol Hill Correspondent
Tax Analysts
05.2011 - 09.2013
Master of Science - Taxation
AMERICAN UNIVERSITY, Kogod School of Business
Certificate - Comparative Tax and Administration
HARVARD UNIVERSITY, Kennedy School of Government
Bachelor of Arts - Political Science and History
UNIVERSITY OF WASHINGTON
Master of Arts - Public Management
JOHNS HOPKINS UNIVERSITY, Kreiger School of Arts And Sciences
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