The Woodard Report Podcast: Featuring Heather Day and Joe Woodard

On this episode of the Woodard Report podcast, Joe speaks with Ron Baker about Peter Drucker's most influential ideas, including the rise of knowledge work, the importance of effectiveness over efficiency, and the need for businesses to pursue future opportunities instead of clinging to the past. They also explore how accounting firms can use distinct brands to separate commoditized services from high-value advisory work as well as why religious leaders offer valuable insights into purpose, dignity, stewardship, and the moral role of business.

About Ron BakerRonald J. Baker began his CPA career with KPMG in 1984. He is the co-founder of THRESHOLD and co-host of The Soul of Enterprise podcast. A renowned speaker and author, he has written eight best-selling books, including Firm of the Future, Implementing Value Pricing and Time's Up. He has educated over 450,000 professionals worldwide and has been named among Accounting Today's Top 100 Most Influential People. A graduate of San Francisco State University, he is also a faculty member of the Professional Pricing Society and a Disney University alumnus.

• HBR interview with Jerry Seinfeld
• The Soul of Enterprise clergy episodes
  • Father Robert Sirico
  • Rabbi Daniel Lapin
  • Mustafa Akyol
• Peter Drucker GPT interview

Thank you to our show sponsor, Puzzle! Puzzle replaces manual quickbooks workflows with AI-driven books built for review, approval, and audit-ready accountability. Learn more at puzzle.io.

Learn more about the show and our sponsors at Woodard.com/podcast

On this episode of the Woodard Report podcast, Heather speaks with Peter McCarroll about why accounting firms must treat AI adoption as a strategic business transformation rather than simply adding new software tools. Peter explains the pricing pressures threatening traditional compliance work, the need to redesign firms around advisory value and human relationships, and how reusable AI instructions and skills can help teams turn individual experimentation into shared, repeatable processes.

About Peter McCarroll Peter McCarroll is a Chartered Accountant (NZ), CPA (Canada), and the founder of The AI Accountant — the only AI training and implementation platform built exclusively for CAS practices. He runs a full-service accounting practice at Fuel Accountants, where he has spent the past two years deploying AI across real client workflows. Peter helps accounting firms move from experimentation to operational transformation — not with theory, but with systems built inside a working practice.

• The AI Champion's Field Guide: What to Do Now, What to Ask For
• Learn more about The AI Accountant
• Learn more about Fuel Accountants
• Connect with Peter on LinkedIn

Thank you to our show sponsor, Bill! Bill is the intelligent way to create and pay bills, send invoices, manage expenses, control budgets, and access the credit your business needs to grow, all in one platform.

Learn more about the show and our sponsors at Woodard.com/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
• Xero targets Australia's medium-sized businesses with launch of Ultra

TV/Movie quote of the week —

• Outcome
• House of the Dragon

Excellent Thing We Learned —

• As AI replaces search, all roads lead to authority

Member spotlight —

• David Williams of CPB Solutions

The Woodard Report article of the week —

• The "Ask Deb" series begins this week!

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 to get started today.

Learn more about the show and our sponsors at Woodard.com/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
• Connect with Jan on LinkedIn

Thank you to our show sponsor, Rightworks! For more information about RightWorks, please visit Rightworks.com.

Learn more about the show and our sponsors at Woodard.com/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
• Microsoft Build 2026: Be yourself at work

TV/Movie quote of the week —

• The Boroughs
• House of the Dragon

Excellent Thing We Learned —

• Insert live valuations of stocks, currency or geographical information right in Excel
• Change Is Not an Event—It's the Environment (from April Rinne's book, Flux)

Member spotlight —

• Connect with Diane Dana on LinkedIn

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

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"
• Pilot is taking a software approach to bookkeeper empowerment called Meridian

TV/Movie quote of the week —

• Schitt's Creek
• Half Man

Excellent Thing We Learned —

• IRS may owe millions of taxpayers refunds for pandemic-era penalty relief

Member spotlight —

• Steve Roderick of Roderick's Payroll

The Woodard Report article of the week —

• Law Firm Bookkeeping Is Not Regular Small Business Bookkeeping

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

Learn more about the show and our sponsors at Woodard.com/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
• Connect with Jessica on LinkedIn

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.

Learn more about the show and our sponsors at Woodard.com/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.

• Learn more about KO Insights
• Connect with Kate on LinkedIn

Thank you to our show sponsor, Rightworks! For more information about RightWorks, please visit woodard.com/podcast.

Learn more about the show and our sponsors at Woodard.com/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
• Ted Callahan, former head of accountant channel at Intuit, is now deputy CTO at Sage

TV/Movie quote of the week —

• The Incredibles
• Project Hail Mary

Excellent Thing We Learned —

• The rule of three
• Not-Us Thinking

Member spotlight —

• Michael McClellan of Aurora Bookkeeping & Consulting

The Woodard Report article of the week —

• Lock It Down, Write It Down (Intuit Security for Firms)

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 to get started today.

Learn more about the show and our sponsors at Woodard.com/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
• Connect with Tyler on LinkedIn

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