Our Spotlight series highlights the careers and lives of tax professionals across the globe. This week’s spotlight is on Jessalyn Dean, an American who has lived and worked in the U.S, Australia, India, Ireland, and now the Netherlands. As a tax consultant with PwC, Dean helps businesses interpret, implement, and automate tax transparency regulations—also known as operational taxes—like 1099/1042-S, QI, FATCA, CRS, and DAC6.
What’s your official title and what does it mean? Senior Manager - Financial Services Tax, which means I have over 10 years of experience in public accounting and taxes. The title also means that most of my clients are in financial services (banks, asset managers, etc.) even though my expertise in tax transparency is broader and can apply to large multinationals and tech companies.
Free time: book, audiobook, or podcast? Podcast, my favorite being Tiny Spark by Amy Costello which investigates criticisms of non-profits, international aid, and philanthropy.
Tax is a huge subject. What’s your area of special interest? Tax transparency, which looks at the reporting of taxes via 1099/1042-S/etc. reporting to the IRS and to the taxpayer but also broader inter-governmental exchanges of tax data such as FATCA, CRS, and more. I call this the mechanisms in between tax authorities and taxpayers that help enforce tax compliance through tax withholding and data reporting/exchanges.
What’s the last movie or show that you watched and loved (DVD, Netflix, or in the theater)? “Klaus,” a unique Santa Claus origin story released in 2019. I’m a sucker for a classic Christmas movie.
What college did you attend and what did you study? Kansas State University in Manhattan, Kan., and I studied accounting and cultural anthropology. All the cool kids were getting masters in accounting or dual finance/accounting degrees but I was more interested in people and culture as my side hustle.
Go to pick-me-up: Coffee or tea? Decaf coffee.
What’s the best tax or financial advice that anyone ever gave you? Don’t stress about setting up super convoluted and complex investment plans for retirement. You’ll be all set putting your money into a few different index ETFs. It really saved me a lot on expensive fees I was paying for other products, simplified my life, and gave me more clarity on my financial outlook than I ever had before.
If you weren’t working in the tax profession, what would your dream job be? Disaster response and coordination. I enjoy working under immense pressure.
If you had the opportunity to make one change in the tax code—an extra credit, a disallowed deduction, whatever—what would it be? I would help 6 million Americans living abroad by striking citizenship-based taxation and replacing it with residence-based taxation like 99% of the rest of the world.
Favorite food, snack, or candy during tax season (or other busy time)? The bad snack: gummy bears. The good snack: green grapes.
What tax news or move made the most impact on your practice or clients this past year? DAC6: the EU Directive on reporting of cross-border tax arrangements.
If Uncle Sam handed you a big tax refund check right now, what would you do with it? Put a down payment on a tiny vacation cottage in the middle of nowhere, either in Italy, Portugal, Ireland, or England.
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