Argi O’Leary brings a unique and versatile background to her role at Ryan, with extensive experience in both litigation and tax operations. Starting her career with early exposure to tax work, Argi developed her expertise over years working in diverse legal roles, including nearly a decade at New York State Tax and Finance, where she led litigation strategy and later managed a large division. Now at Ryan, she leverages her broad tax knowledge and commitment to client advocacy. In this interview, Argi shares insights on her unconventional path, her approach to success, and her dedication to achieving fair outcomes for clients.
Q: Can you tell me about your background and how you got started in the tax industry?
A: My first job was actually in tax—I was probably 11 years old, working on Saturday mornings at the Certified Public Accountant (CPA) firm where my mom worked. I handled tasks like updating CCH books and swapping out pages—tedious work, but I was happy to have a little paycheck. Later, I went to college and law school and pursued non-tax roles as a prosecutor in Manhattan, a law firm associate, and as a clerk for a judge.
After about five years at my law firm, a partner asked if I’d consider a position with Governor Cuomo’s administration, which led to a role at New York State Tax and Finance managing litigation for the agency. My work there included tax controversy and other litigation-focused matters. Over nearly 10 years, I transitioned into an operational role, overseeing a large division within the agency.
Q: What specific areas of tax do you specialize in, and what led you to focus on these areas?
A: I don’t really specialize in one area of tax. When I first joined New York State Tax and Finance, I worked on whatever hot topics the agency was focused on, whether corporate tax, sales tax, or other smaller taxes. This variety continued here in my role at Ryan, where our Advocacy practice involves a wide range of tax issues across different service areas. My day could cover federal tax issues, sales tax, income tax, or fuels. It’s similar to my background in litigation, where you become the expert on the issue at hand, and that’s the approach I take in tax as well.
Q: What is the proudest moment in your career?
A: This may be an unusual answer, but I’d say it was navigating my team through the early days of the pandemic. At that time, I was managing a large division at New York State Tax and Finance, with some staff working around the clock. Helping my team and the agency make quick decisions to keep people safe while still getting the work done was a challenging and meaningful experience. It wasn’t just a single moment but rather a collection of moments as we worked through those unprecedented times.
Q: How do you measure the success of your work with clients?
A: At Ryan, we place a strong emphasis on client satisfaction surveys, which is great—we should be asking clients how we did. I also think success is reflected in whether the client rewards us with additional work. When clients see the value we add, they often want to continue the partnership, which is a good indicator that we’ve achieved successful outcomes for them.
Q: What do you find most rewarding about working in the tax industry?
A: In my role at Ryan, I find our advocacy motto, “getting fair answers faster,” to be especially rewarding. We understand that governments need tax revenue to provide essential services, but we also believe in ensuring that the process is fair and makes compliance easier for taxpayers. It’s about helping taxpayers get clear answers so they can comply efficiently. When we achieve that, we feel we’ve delivered for the client. When I was on the government side, it was about making sure our teams understood the importance of responsiveness to taxpayers so they could meet their compliance obligations as smoothly as possible.
You can find out more about Argi O’Leary here.
