The Woodard Report Podcast: Featuring Heather Satterley and Joe Woodard

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]

Episode 174 - Firing Clients, Finding Your Niche, and Making Accounting Fun - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Heather speaks with Tyler Otto about his unconventional path into accounting, growing a firm, and how niching down helped strengthen both company culture and client relationships. Tyler shares candid advice on when and how to "fire" difficult clients, what red flags to watch for during prospecting, and why firm owners should prioritize cultural fit over revenue. The conversation also dives into Tyler's upcoming live game show at Scaling New Heights, and practical ways accounting firms can safely experiment with AI while preparing for the future of the profession. About Tyler Otto Tyler Otto is the president and owner of Specialized Accounting, a thriving seven-figure remote firm dedicated to the hospitality industry. Before joining forces with his wife Karen at her solo practice, Tyler honed his finance chops with leadership roles at Vail Resorts and Imprint Hospitality. Known for his energy and approachability, Tyler is passionate about collaboration with fellow professionals and welcoming new accountants to the field. He's presented at major accounting, tech, and hospitality conferences and recently launched Firm Foundation, a step-by-step course turning firm-building from daunting into doable. Whether behind a microphone or trading insights on podcasts, Tyler brings both expertise and a dash of fun to any discussion. * Learn more about Specialized Accounting [https://www.specializedat.com/] * Connect with Tyler on LinkedIn [https://www.linkedin.com/in/tylerdotto/] Thank you to our show sponsor, Woodard! The Woodard membership program will help you build your ideal practice with our coaching, education, community, and resources. We'll get you there with strategic direction from experienced pros, access to skill building and resources, and a community to continually inspire your practices transformation. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/podcast]

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

On this episode of the Woodard Report podcast, Joe and Heather speak about the rapid acceleration of AI and how it is reshaping the accounting profession, from audit and compliance work to more advisory-focused roles. They explore the importance of maintaining the "soul" of a business in an increasingly automated world, discuss the rise of AI agents and emerging technologies, and share insights on how accountants can adapt by leaning into their uniquely human strengths. Current events — * KPMG closes U.S. federal audit practice, trims advisory staff [https://www.accountingtoday.com/news/kpmg-closes-u-s-federal-audit-practice-trims-advisory-staff] * META Lays off about 10% its workforce [https://www.npr.org/2026/04/23/nx-s1-5797855/meta-layoffs-10-percent-staff] TV/Movie quote of the week — * Company Retreat [https://www.imdb.com/title/tt22074164/] * The Pitt [https://www.imdb.com/title/tt31938062/] Member spotlight — * Thrive Business Services [https://thrivebusinessservices.net/] The Woodard Report article of the week — * The Sacred Ritual of Month-End (An Accountant's Comfort Blanket) [https://report.woodard.com/articles/the-sacred-ritual-of-month-end-an-accountants-comfort-blanket-opawr-opdwr] 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]