Ask the Experts — LIVE! Your Toughest Compliance Questions Answered

It's back, and it's time to tackle the compliance questions that had our inbox buzzing.

Our Ask the Expert column fields hundreds of questions each month, but some stick out from the rest: the ones that expose gray areas in the regulations or make you rethink a process you thought you'd nailed. In this special live session, we're pulling back the curtain on the toughest, most talked-about compliance questions we've received recently and giving you the expanded answers you won't find in the column.

In this fast-paced hour, we'll dig into real-world compliance questions on:

• W-9 compliance: the edge cases and red flags that trip up even experienced practitioners
• International reporting: navigating the complexity of cross-border payee documentation and reporting obligations
• Compliance risk exposure: what recent enforcement trends reveal about the gaps lurking in your AP/tax processes

And because compliance news doesn't wait for a webinar calendar, we're holding time on the agenda for late-breaking developments, including the long-awaited revised W-9, if it drops before we go live.

Whether you're troubleshooting your own tricky situation or just want to stay ahead of what's tripping up your peers, this session delivers practical, straight-talk compliance answers, live, and straight to the point.

Jason Dinesen 
President, Dinesen Media Ventures

Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason prepared tax returns and provided accounting services as a practicing accountant from 2009 through the summer of 2025.

He’s also the founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals, to podcast production to radio and journalism content.

Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics. Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe’s in West Des Moines, Iowa. He is IOFM’s go-to person for anything related to 1099s and information reporting.

Grace Berube
Senior Content Manager, IOFM

Grace is the Senior Content Manager at the Institute of Finance & Management (IOFM), where she has led content strategy and development since 2022. In this role, she oversees all aspects of IOFM’s digital and event-based content, ensuring it remains timely, relevant, and actionable for all financial operations professionals.

Grace manages IOFM’s robust library of site content, leads the organization’s editorial and member webinar programming, and hosts IOFM’s podcast series. She also oversees a team of subject matter experts who contribute thought leadership and educational articles. In additional, Grace curates and manages all speaker content for IOFM’s in-person and virtual events, ensuring consistency and quality across every touchpoint. With nearly three years in the role, Grace brings a deep understanding of the financial operations landscape and a passion for delivering content that empowers professionals to excel in their roles.