Senior federal policy strategist with landmark wins in legislation and regulation — and the rare ability to build the AI tools that give organizations an advocacy edge.

15+ years navigating Congress, the IRS, and federal agencies. The rare DC professional who doesn't just advise on what's coming — but builds the tools to act on it.

$65B

Federal funds secured for 19,000 municipalities

$15B

Infrastructure unlocked via landmark IRS ruling

50,000

Taxpayers granted permanent tax relief

15+ yrs

Federal policy, legislation & regulatory advocacy

Michael Gleeson

About

I've spent my career at the intersection of federal tax law, legislative strategy, and government affairs — working on Capitol Hill as tax counsel, inside the IRS as a legal technician, and as a senior leader for one of Washington's most influential municipal advocacy organizations. I've authored legislation, won landmark IRS rulings, and helped move $65 billion in federal resources to American cities.

What sets me apart now: I build. While most senior DC professionals advise, I develop full-stack AI-powered platforms that help government affairs teams work faster, spot opportunities earlier, and operate at a level that wasn't possible three years ago. That combination — deep institutional knowledge plus hands-on technical capability — is what I bring to an organization.

IRS Office of Chief CounselNational League of CitiesU.S. House of Representatives — Ways & Means

Career

2024–2025

Tax Law Specialist

IRS, Office of Chief Counsel

  • Directed legal review of the national Free File program.
  • Built a precedent database that accelerated expert reviewer guidance across the Office of Chief Counsel.
  • Upskilled cross-functional attorney teams on complex fiscal policy.

2022–2024

Director, Finance, Administration & Intergovernmental Relations

National League of Cities

  • Secured the decisive 50th Senate vote for the American Rescue Plan Act, unlocking $65B in State and Local Fiscal Recovery Funds for 19,000 municipalities.
  • Spearheaded an IRS Revenue Ruling on lead-pipe replacement, unlocking $15B in infrastructure investment.
  • Co-authored the definitive national guide on Clean Energy Tax Credits — #1 Google ranking for 8 weeks, capturing 13% of total organizational web traffic.

2020–2022

Manager → Director

National League of Cities

  • Authored Congressional testimony for the organization's President before the U.S. House.
  • Directed federal lobbying campaigns on tax policy and OMB Uniform Guidance.

2018–2020

Founder & Principal

Michael Gleeson & Associates

  • Founded and led a federal government affairs consultancy serving a diverse client portfolio.

2017–2018

Vice President, Special Situations

Height Capital Markets

  • Authored definitive TCJA analyses for national investors and C-suite executives.
  • Conducted fiscal impact modeling for high-volatility market transitions.

2017

Director, Government Relations

National Grocers Association

  • Advanced fiscal interests of the independent grocery sector before House Ways & Means and Senate Finance.
  • Invited twice as SME for Congressional Caucus briefings.

2013–2016

Tax Counsel

Office of Congressman Jim McDermott, U.S. House

  • Authored and secured bipartisan support for the Student Tax Relief Act.
  • Navigated provisions into a Treasury Revenue Procedure granting permanent relief to 50,000 taxpayers.

2011–2013

Capitol Hill Correspondent

Tax Analysts

  • Lead policy correspondent covering landmark legislation including the Fiscal Cliff (American Taxpayer Relief Act) for 150,000 tax professionals nationwide.

Guest Lecturer, Master of Taxation Program — American University Kogod School of Business (2016–2022)

What I Build

Beyond client work, I build and license AI-powered software platforms for the government affairs industry. Most senior DC professionals don't ship software. I do — because understanding what's technically possible changes how you approach advocacy strategy.

GovAffairs Job Scout

AI-powered job search intelligence for Washington DC government affairs professionals

A full-stack AI platform built on Flask, SQLite, and Claude AI. Features include AI-generated resume tailoring, org watch lists, contact intelligence, and a built-in application tracker. Designed for Director and VP-level government affairs professionals navigating the DC job market.

FlaskSQLiteClaude AIPythonFull-stack
Live product

Capitol Lens

Lobbyist intelligence dashboard for DC government affairs professionals

A premium intelligence platform that aggregates and surfaces actionable data on registered lobbyists, lobbying firms, and client relationships across the federal government affairs landscape. Built for practitioners who need to track the field, not just participate in it.

FlaskSQLitePythonData aggregationFull-stack
Live product

Capitol Hill Staffer Simulator

AI-powered training tool for Hill staff and government affairs professionals

An interactive AI simulation platform that replicates the dynamics of Capitol Hill staff interactions — allowing government affairs professionals and advocates to practice, prepare, and sharpen their Congressional engagement skills before the real meeting.

Claude AIPythonFlaskFull-stack
Live product

Get in touch

Available for senior federal affairs, government relations, and tax policy roles. Based in the Washington DC area.