Episode 173 - AI, Humanity, and the Future of Accounting - The Woodard Report Podcast

Episode 179 - Change Is the Environment - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe and Heather speak about Microsoft's latest quantum computing and AI developments, and what those shifts could mean for accounting professionals. They also connect lessons from TV, April Rinne's book Flux, and Donna Reed's article on client conversations to the importance of adaptability, empathy, and intentional decision-making in advisory work. Current events — * Microsoft's New Quantum Chip Aiming for Useful Machine in 2029 [https://www.msn.com/en-us/lifestyle/shopping/microsoft-s-new-quantum-chip-aiming-for-useful-machine-in-2029/ar-AA24FDeY] * Microsoft Build 2026: Be yourself at work [https://blogs.microsoft.com/blog/2026/06/02/microsoft-build-2026-be-yourself-at-work/] TV/Movie quote of the week — * The Boroughs [https://www.imdb.com/title/tt27557289/] * House of the Dragon [https://www.imdb.com/title/tt11198330/] Excellent Thing We Learned — * Insert live valuations of stocks, currency or geographical information right in Excel [https://support.microsoft.com/en-us/excel/excel-data-types-stocks-and-geography] * Change Is Not an Event—It's the Environment (from April Rinne's book, Flux) [https://www.amazon.com/Flux-Superpowers-Thriving-Constant-Change-ebook/dp/B08Z3D14TC] Member spotlight — * Connect with Diane Dana on LinkedIn [https://www.linkedin.com/in/diane-danna-3273257] The Woodard Report article of the week — * The Quiet Question that Improves Every Client Conversation Thank you to our show sponsor, Zoho! Zoho is a unique and powerful software suite to transform the way you work, designed for businesses of all sizes, built by a company that values your privacy. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast]

Episode 178 - Current Trends, Human Connection, and the Future of Advisory - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe and Heather speak about emerging developments shaping the accounting profession, including the consolidation of New England CPA societies, Pilot's shift from a local partnership model to AI-powered bookkeeping software, and how firms can use automation to elevate, not replace, their advisory services. They also explore the importance of healthy client boundaries, lessons from popular TV shows, recent IRS penalty relief opportunities, and why uniquely human qualities like navigating uncertainty and building relationships remain essential in an AI-driven future. Current events — * 5 New England State CPA Societies merge to form "New England Society of CPAs" [https://www.cpapracticeadvisor.com/2026/06/01/new-england-society-of-cpas-formed-after-merger-of-5-state-societies/184284/] * Pilot is taking a software approach to bookkeeper empowerment called Meridian [https://meridian.pilot.com/] TV/Movie quote of the week — * Schitt's Creek [https://www.imdb.com/title/tt3526078/] * Half Man [https://www.imdb.com/title/tt32767294/] Excellent Thing We Learned — * IRS may owe millions of taxpayers refunds for pandemic-era penalty relief [https://www.cnbc.com/2026/05/11/kwong-v-united-states-tax-refund-deadline.html#:~:text=Millions%20of%20Americans%20could%20be%20eligible%20for%20tax,from%20Jan.%2020%2C%202020%2C%20through%20July%2010%2C%202023.?msockid=148b7175a4046cbb3659663ea5b26dd9] Member spotlight — * Steve Roderick of Roderick's Payroll [https://www.roderickspayroll.com/] The Woodard Report article of the week — * Law Firm Bookkeeping Is Not Regular Small Business Bookkeeping [https://report.woodard.com/articles/law-firm-bookkeeping-is-not-regular-small-business-bookkeeping-olswr] Thank you to our show sponsor, Puzzle! Puzzle, the next generation firm, AI-powered, human-led. Puzzle replaces manual quick books workflows with AI-driven books built for review, approval, and audit-ready accountability. Learn more at puzzle.io [https://puzzle.io/] Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast]

Episode 177 - From Startup Founder to Autonomous Bookkeeping: How Pilot Built the Future of Accounting - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe speaks with Jessica McKellar about her journey from studying computer science at MIT and building successful software startups to founding Pilot, a bookkeeping and accounting technology company. Jessica shares how Pilot evolved from solving the financial back-office challenges faced by entrepreneurs into a platform and explains how automation, AI, and value-based pricing are reshaping the economics of accounting firms. She also introduces Meridian, Pilot's new platform that enables autonomous bookkeeping, month-end close processes, and AI-assisted accounting workflows designed to help firms scale while improving both client and employee experiences. About Jessica McKellar Jessica McKellar is the co-founder and CEO of Pilot. She started the company with a simple conviction: small business owners shouldn't have to be their own bookkeeper, accountant, and financial advisor all at once. Today, Pilot serves more than 3,500 businesses, from neighborhood restaurants and retail shops to growing service businesses, helping owners get books off their plates so they can focus on what actually grows their company. Before Pilot, Jessica founded two other companies that were acquired by Oracle and Dropbox. She holds 3 degrees from MIT. Jessica also teaches programming at San Quentin State Prison and advocates for hiring formerly incarcerated people. She believes that excluding talented workers based on their records doesn't make business sense, and that second chances belong in the workplace too. * Learn more about Meridian from Pilot [https://meridian.pilot.com/] * Connect with Jessica on LinkedIn [https://www.linkedin.com/in/jesstess/] Thank you to our show sponsor, Canopy! Unclunk your firm with Canopy, the fully integrated practice management that helps accountants build the firm they always wanted. The suite includes client and document management, workflow, time and billing, engagements and proposals, and more. Check out GetCanopy.com [https://www.getcanopy.com/]. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast].

Episode 176 - The Tech Humanist: Keeping Humanity at the Center of AI - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe speaks with Kate O'Neill about the intersection of technology and humanity, exploring how businesses can embrace AI and automation without losing the human connection that drives trust, meaning, and purpose. They discuss why accounting professionals should view AI not as a replacement, but as an opportunity to shift from transactional work to more strategic, empathetic, and judgment-driven client relationships. The conversation also dives into the risks of over-automation and why human wisdom, context, and lived experience remain irreplaceable in an increasingly tech-driven world. About Kate O'Neill Kate is the founder of KO Insights, helping leaders and organizations make future-ready, meaningful, and ethical decisions about technology and innovation. She's a former digital strategist for Netflix and early Google, and the author of 6 books, 4 of which are in tech and business including Tech Humanist and What Matters Next [https://woodard.monday.com/1ffbe2b1f9458019acc5d7c917e1c7de?pvs=25]. * Learn more about KO Insights [https://www.koinsights.com/] * Connect with Kate on LinkedIn [http://linkedin.com/in/kateoneill] Thank you to our show sponsor, Rightworks! For more information about RightWorks, please visit woodard.com/podcast [https://www.woodard.com/podcast]. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast]

Episode 175 - AI, Intuit Upheaval, and the Future of Accounting - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Heather and Joe talk about major developments shaping the accounting profession, including Intuit's dramatic stock decline, workforce layoffs tied to AI adoption, and the launch of ChatGPT Finance. They also explore how artificial intelligence is rapidly transforming professional services, emphasizing the need for accountants to embrace change by leaning into human-centered skills like judgment, relationships, and advisory work. Along the way, they share productivity strategies, discuss the dangers of "not us" thinking around AI disruption, and spotlight a successful bookkeeping professional building a high-value, relationship-driven practice. Current events — * Intuit's Stock Plunge and other troubles [https://www.benzinga.com/pressreleases/26/05/g52860943/intuit-stockholder-alert-bragar-eagel-squire-p-c-is-investigating-intuit-inc-on-behalf-of-intuit-s] * Ted Callahan, former head of accountant channel at Intuit, is now deputy CTO at Sage [https://www.linkedin.com/posts/tedcallahan_thanks-all-who-reminded-me-yes-its-may-ugcPost-7465905449729691648-ho6K/] TV/Movie quote of the week — * The Incredibles [https://www.imdb.com/title/tt0317705/] * Project Hail Mary [https://www.imdb.com/title/tt12042730/] Excellent Thing We Learned — * The rule of three [https://add.org/adhd-procrastination/] * Not-Us Thinking [https://a.co/d/0gV9ph3Z] Member spotlight — * Michael McClellan of Aurora Bookkeeping & Consulting [https://www.aurorabookkeeping.com/] The Woodard Report article of the week — * Lock It Down, Write It Down (Intuit Security for Firms) [https://report.woodard.com/articles/lock-it-down-write-it-down-intuit-security-for-firms-lock-it-down-write-it-down] Thank you to our show sponsor, Digits! Digits is the world's first agentic general ledger. It is accounting software that works for you. Built from the ground up for the AI era, Digits automates bookkeeping in month end, shifting your team from data entry to review and advisory. Visit Digits.com [https://digits.com/] to get started today. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast]