Episode 181 - Moving Upmarket (and Making Business More Human) - The Woodard Report Podcast

Episode 181 - Moving Upmarket (and Making Business More Human) - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe and Heather talk about Xero's move into the midmarket, why accounting firms may find greater opportunity above the AI disruption zone, and how empathy can defuse difficult client conversations. They also discuss how personal transformation can lead to a healthier, more successful practice. Current events — * NJ Considers Pet tax credit [https://www.cpapracticeadvisor.com/2026/07/16/a-900-tax-break-for-pet-owners-new-jersey-is-considering-it/186766/] * Xero targets Australia's medium-sized businesses with launch of Ultra [https://www.xero.com/au/media-releases/xero-targets-medium-businesses-with-ultra/?utm_source=press%20release] TV/Movie quote of the week — * Outcome [https://www.imdb.com/title/tt23724682/] * House of the Dragon [https://www.imdb.com/title/tt11198330/] Excellent Thing We Learned — * As AI replaces search, all roads lead to authority [https://www.accountingtoday.com/opinion/as-ai-replaces-search-all-roads-lead-to-authority] Member spotlight — * David Williams of CPB Solutions [https://cpbsolutions.com/] The Woodard Report article of the week — * The "Ask Deb" series begins this week! [https://report.woodard.com/articles/author/debra-kilsheimer] Thank you to our show sponsor, Digits! Digits is the world's first agent general ledger, accounting software that works for you. Built from the ground up for the AI era, Digits automates bookkeeping in month and 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 180 - From Compliance to Capacity: Building an AI-Enabled Accounting Firm - The Woodard Report Podcast

On this episode of the Woodard Report podcast, Joe speaks with Jan Haugo about how accounting firms can move beyond experimenting with AI and begin using it to transform workflows, increase profitability, and create more capacity for strategic advisory services. Jan shares practical approaches for overcoming security concerns and uncertainty, including her "pain, problem, prompt" method, while emphasizing the importance of firmwide training, strong governance, and leadership-driven adoption. They also explore how AI can help accountants become more thoughtful, empathetic advisors by freeing them to focus on the goals and challenges that matter most to their clients. About Jan Haugo Jan Haugo Vuicich is the founder of SmartAccountant.AI, an AI training and implementation company built for accounting professionals, by someone who spent years doing the actual work. She was named to MSN's Top 10 AI Leaders to Follow in 2026 and co-authored Intuit's AI Certification curriculum. Before any of that, she was running a small accounting practice, finishing her degree over a decade as a single mom, and logging 70+ hour weeks. That history is what makes her training different. She is not teaching from the outside. She built her frameworks from inside the same workflows her clients are trying to fix. Through SmartAccountant.AI, Jan runs the SMART Method Bootcamp, a foundational AI training program that has seen 100% adoption among participants, along with done-with-you training and direct AI implementation for firms ready to make real operational changes. She works with solo practitioners through mid-size accounting firms across the country, and the work is the same regardless of firm size: help owners and their teams reclaim their time, price their services at the level the work actually deserves, and build practices that hold up outside of tax season too. * Learn more about SmartAccountant.AI [https://smartaccountant.ai/] * Connect with Jan on LinkedIn [https://www.linkedin.com/in/janhaugo/] Thank you to our show sponsor, Rightworks! For more information about RightWorks, please visit Rightworks.com [https://www.rightworks.com/]. Learn more about the show and our sponsors at Woodard.com/podcast [https://www.woodard.com/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].