AI in accounting - Team member or tool?

In this episode, Damien and Penny take a hard look at how accounting and bookkeeping firms build — and bloat — their technology stacks. From firms running their entire practice on email and CCs to those juggling multiple practice management systems stitched together with Zapier, they make the case for standardization over accumulation. Drawing on Penny's "little black dress" analogy and real-world examples from hundreds of firms, this episode is a practical guide to auditing what you have, using what you already own, and letting your ambition — not the trade show floor — drive your tech decisions.Key Topics:Stop bolting on — Why buying a second practice management tool (and a third, and a fourth) to fill a single gap creates overlap, bloat, and cost nobody is trackingThe Little Black Dress analogy — Penny's framework: pick a standard core tech stack (the dress) that works across your firm, then accessorize with client-facing apps (the shoes, scarf, and pocketbook) — not the other way aroundProcess should match ambition — Define what your firm is trying to do and who you serve first; then choose technology that supports that — don't let a tool's feature list dictate your strategyThe October 15 problem — How tax deadlines expose firms that haven't built proper systems, capacity, and workflow before layering on CAS servicesPractice management fundamentals — The non-negotiable "who, what, when, where, and how" every firm needs; why running a practice on email means nobody is accountable and no ambition is reachable"Good enough" beats perfect — Bundled tools like Microsoft 365's booking and whiteboard features may be all you need right now; the pursuit of the perfect tech stack gets in the way of progressThe 17–20% problem — Most firms only use a fraction of the technology they've already paid for; Damien and Penny discuss how to surface what's already in your existing tools before buying something newThe Red/Amber/Green tech audit — A practical team exercise: list every app, rate each one for usability, support responsiveness, and value, and identify what to keep, review, or cut as part of your FY26 planningWorkflow vs. tasking — Penny's distinction: workflow is the noun (the full journey from A to Z); tasks are the verbs (the individual steps in between)One person, one minor need — Mark Albrecht's rule: don't change your tech for one person's one small requirement — wait until four or five people are asking for the same thingDoug Gocke case study — How a non-accountant COO doubled a four-partner firm's revenue and profitability by focusing relentlessly on who, what, where, when, and why (find Doug's episode on CPA Trendlines and Spotify — search "Gocke")

Most accounting firms are bracing for AI to replace them. Trent Yesberg went a different direction: he used Claude and ChatGPT to build automation inside his own firm, then turned the industry's most annoying billing problem into a software company. This is what it actually looks like when a working firm goes AI-native, not a slide deck version of it.What You'll LearnHow Regional Business Services built automated client reporting workflows using scripts written by Claude, without paying ongoing AI costs to run themWhy a non-technical team member can build real production automation just by describing a workflow in plain languageThe “forward deployed engineer” model AI companies use internally, and why accountants are already positioned to run itHow to tell which software vendors in your tech stack will survive the shift to agentic AI, and which will struggleHow Trent's firm cut a full day of monthly billing work down to about thirty minutes, and recovered revenue it had been quietly missingWhat Trent expects to happen to his own client base over the next twelve months as AI adoption splits the marketGuest BioTrent Yesberg is a co-founder of Twine Apps and director of Regional Business Services (RBS), an accounting firm in Townsville, North Queensland that was a repeat finalist, and eventual winner, of Intuit's Firm of the Future award. He built Twine Biller, a subscription rebilling tool for accounting and bookkeeping firms, out of a problem he lived inside his own practice.Connect with Trent on LinkedIn.Check out our SponsorsMoneyPenny, LLC for outsourced backoffice tax and accounting support.TwineApps for simplified subscription billing.Connect with the HostsDamien GreatheadPenny BreslinLinks referenced in this episode:bill.commoneypennyllc.comtwineapps.co

Up to 30 percent of your firm's work might be invisible, never scheduled, never billed, and never counted when it's time to talk about capacity or fees. Jeanne Hardy, founder of the practice management platform Levvy and the CAS firm Creative Business, joins Damien and Penny to explain what that ad hoc work is costing firms, and how a "noise-canceling" approach to practice management can fix it.Key Topics CoveredWhat client advisory services actually means, beyond the buzzwordHow niching around creative business owners built a 20-year CAS practiceWhy tribal knowledge trapped in people's heads is the real barrier to good AIThe 25 to 30 percent of firm time that never gets tracked or billedHow agentic AI is already automating accounts payable at Levvy00:00 — Welcome, sponsors, and catching up02:00 — Meet Jeanne Hardy: from Creative Business to founding Levvy04:00 — What does "CAS" actually mean?08:00 — Niching down around creative business owners13:00 — Why most practice management tools create noise instead of clarity20:00 — The tribal knowledge problem: what happens when it only lives in someone's head22:00 — Why context is the fuel AI actually needs28:00 — The invisible work: 25 to 30 percent of a firm's time is ad hoc33:00 — Radical transparency and fixing team burnout with time data37:00 — Talking to your team about AI without the fear38:00 — Inside Levvy's first agentic workflow: automating accounts payable40:00 — Why advisory work is the future the next generation actually wants44:00 — Where the name "Levvy" came from, and where to find JeanneAbout our GuestJeanne Hardy is the CEO and founder of Levvy, a practice management platform built for CAS firms, and the founder of Creative Business, a CAS firm serving creative entrepreneurs. Connect with her on LinkedIn.Check out our SponsorsMoneyPenny, LLC for outsourced backoffice tax and accounting support.TwineApps for simplified subscription billing.Connect with the HostsDamien GreatheadPenny Breslin

This podcast episode elucidates the critical importance of establishing robust processes, policies, and procedures within accounting and bookkeeping firms. We delve into the nuances of Client Advisory Services (CAS) and emphasize that the success of such services is fundamentally rooted in effective bookkeeping practices. Through our discussions, we highlight the myriad challenges firms face when they lack standardized methodologies, illustrating the detrimental impact on client service and operational efficiency. Takeaways:The podcast emphasizes that effective client advisory services rely heavily on well-structured processes, policies, and procedures.Listeners are encouraged to conduct internal assessments of their firm's policies to ensure alignment with current practices and technologies.The hosts highlight that outdated procedures can lead to inefficiencies and errors, especially during critical busy seasons.Implementing technology to streamline workflow and task management is essential for enhancing productivity and client satisfaction.The discussion reveals that many firms underutilize their technology, employing only a fraction of its intended capabilities, which hampers overall performance.Lastly, the importance of having team members articulate and understand procedures is underscored to avoid miscommunication and errors in execution.

Building a successful client accounting services practice isn't just about choosing the right software or pricing model — it starts with the clients you choose and how openly you communicate with your team about what drives profit.In this episode, co-hosts Damien Greathead and Penny Breslin field listener questions on some of the most pressing operational challenges facing CAS firm owners today. The conversation opens with a deceptively simple question: how much should your team know about client profitability? Penny and Damien unpack why sharing the profitability of services — rather than individual client financials — can help your team understand the impact of scope creep, delays and inefficiency, without exposing sensitive numbers.From there, they dig into the real-world damage caused by clients who chronically delay. Penny shares how repeated bottlenecks from a handful of clients can derail an entire workflow, stress the team and block the path to higher-value advisory work. They discuss practical strategies for identifying the root cause of delays — whether it's missing documents or unanswered questions — and adapting your communication method to suit each client.The episode also covers the case for vertical specialisation, with real examples of firms that specialised in breweries, dental practices and restaurants, including how deep industry knowledge helped one firm help clients pivot through COVID lockdowns. Damien and Penny close with a candid discussion on AI's actual impact on accounting workflows and the realities of using offshore teams, including why team buy-in matters more than client perception.IN THIS EPISODEUnderstand why service-level profitability matters more than client-level profitability — and how to share that insight with your team without exposing sensitive financial dataIdentify and manage chronic client delays before they derail your entire workflow and block the path to advisory workSeparate "missing information" from "missing documents" in your workflow statuses to diagnose the real cause of bottlenecksDiscover how vertical specialisation can sharpen your marketing, reduce overheads and make your firm the go-to expert in an industryHear real examples of firms that specialised and thrived — including a restaurant specialist who helped clients pivot to distilleries during COVID lockdownsLearn how to respond when clients ask whether AI should reduce your fees — and why the reality of AI in bookkeeping is far messier than the marketing suggestsUnderstand what it takes to make offshore teams successful — and why internal team buy-in matters more than client perceptionExplore how to communicate the value of monthly CAS services to clients who only see the worth of annual compliance workCompanies mentioned in this episode:Moneypennyllc.comQuickBooksXero

AI in Accounting: Team or Tool?Is AI a team member, a tool, or both? In this episode, Damien Greathead and Penny Breslin dig into how AI is actually being used inside accounting and bookkeeping practices today — not in theory, but in the day-to-day. Penny walks through a real client cleanup project where she used Claude to turn a messy Excel breakdown into a client-ready proposal in minutes (and caught the AI's own math mistake along the way). The conversation moves into what this means for team development — how firms need to intentionally build critical thinking skills in their people so they don't become passive "bot approvers," and why understanding the full context of a client (not just the transaction data) still requires a human. They close with practical advice on how to write better AI prompts by giving the "set and setting," and where to find more from Penny and Damien.Time Stamps:0:00 — Intro: welcome to It's Not Just The Numbers, meet your hosts1:49 — Is AI a team member or a tool? Opening debate7:31 — Real case study: using Claude to build a client cleanup proposal from a messy Excel file19:17 — Shifting focus to the team: what AI means for an 80-person accounting staff21:07 — Teaching critical thinking skills in a technical, linear-trained workforce23:34 — The "rainforest" mindset: seeing complex opportunity instead of fixating on crisis26:25 — Gamifying work with AI to build critical thinking habits31:33 — "Set and setting": how to prompt AI like you'd brief a team member38:42 — Where to find Penny and Damien, and closing thoughts

Tax season looked different in 2026, and it's not just volume. In this episode, Damien Greathead and Penny Breslin unpack the real AI story inside accounting firms: a live test of Juno saved 25% of prep time, clients are submitting documents faster than ever, and AI meeting assistants are replacing manual notetaking. But the bigger conversation is about critical thinking. As AI handles more routine work, who's making sure your team can still spot the anomaly? Identify the conflict? Give a client a real perspective? Damien shares how Moneypenny is gamifying judgment, hiring non-accountants, and rebuilding firm roles around advisory rather than compliance. This is a practitioner episode — real tools, real results, real friction. If you're building or scaling a CAS practice, this one is essential listening.Thank you to our sponsors MoneyPenny, LLC. From bookkeeping and tax preparation to back-office support, MoneyPenny helps accounting firms increase capacity, improve efficiency, and grow with confidence. In This EpisodeWhy accounting firms are seeing earlier tax document submissions in 2025Live AI tax prep test: Juno delivers ~25% time savings, but still requires human reviewThe difference between OCR tools (Grunt Works, Shore Prep, 1040 Scan) and AI-layer toolsHow AI can find conflicting information across reports, workflows, and client communicationsThe 'trust but verify' mindset, and why anomaly-hunting beats confirmation-seekingGamifying critical thinking to keep accounting teams sharp in an AI-assisted environmentThe 80/20 rule: who will rise to the top as AI takes over routine tasksBuilding distinct firm roles: traffic cop, trusted advisor, tax expertWhy MoneyPenny is hiring data scientists instead of more accountantsConnect with the hosts on LinkedInDamien GreatheadPenny Breslin

In this special "After Hours" episode, hosts Damien Greathead and Penny Breslin sit down with Steven Ladd — recovering engineer, serial entrepreneur, and small business advisor — to explore what it really means to serve small business owners beyond the debits and credits.Steven shares his journey from engineer to entrepreneur to advisor, and how working with small businesses during COVID revealed a hard truth: most owners don't have a financial foundation — and most advisors don't know how to connect with them on a human level.In this episode, you'll hear about:Why speaking plain English (not EBITDA) changes everythingThe "Lemonade Stand" model for helping owners understand their own businessWhat the Catalyst program looks like in practice — and what real value delivery looks like in the first 90 daysThe difference between a compliance mindset and a true advisory relationshipWhy the best advisors ask great questions rather than have all the answersWhether you're an accountant looking to move into advisory, or a bookkeeper ready to offer more value, this conversation will give you the confidence and framework to take that next step.0:00 – Introduction & Welcome 0:22 – About the "After Hours" format 0:54 – Recap of previous episode: Defining Advisory Services 1:51 – Penny introduces Steven Ladd 4:17 – Steven's background: Engineer → Entrepreneur → Advisor 5:09 – Working with small businesses through COVID 8:28 – How Steven describes what he does: "Love and Systems" 10:40 – Why jargon (like EBITDA) gets in the way 16:35 – What the Catalyst program looks like in practice 17:10 – The "Lemonade Stand" model for business clarity 24:15 – After the Catalyst: bookkeeping options & the fork in the road 29:13 – Empowering owners to become the Operator 31:15 – How big is Steven's company? (The answer may surprise you) 32:44 – A client success story: from skeptic to $250K loan 35:46 – Wrap-up & connect with Steven on LinkedIn

Are your accounting firm's processes truly optimized, or are you considering automation as a quick fix to deeper workflow issues? In this episode, hosts Damien Greathead and Penny Breslin are joined by Korey Cournoyer to explore the world of automation within accounting firms. They discuss the importance of process documentation, the benefits of strategic automation, and how to approach implementation effectively. The conversation highlights the need for standardization, efficient workflows, and proper utilization of technology to ensure success. Korey emphasizes the significance of understanding why automation is needed and addressing those issues internally before implementation.Korey is the CEO of STRMS.io, which works within the accounting and finance industry to help firms document, optimize, and automate their workflows and processes. He is not building another app for firms to deploy but is helping build custom automations that help firms scale by connecting their existing apps across their existing workflows. His company supports firms looking to scale without exponentially increasing headcount or costs. Before co-founding STRMS, Korey helped grow and scale an accounting firm, GrowthLab Financial, for over nine years. [00:00 - 14:45] Intro and The Importance of Process DocumentationDamien, Penny, and Korey discuss the critical role of process documentation in successful automation.Understand the need for standardization before implementing automation solutions.Korey explains his company's approach to helping firms identify automation opportunities.Clear process mapping is crucial for effective automation implementation.[14:46 - 27:14] Benefits of Automation Automation can improve efficiency, reduce errors, and enhance client experiences.Emphasize the importance of transparency with employees about automation goals.Identify areas where automation can positively impact employee satisfaction and retention.Korey shares insights on focusing on high-value, repetitive tasks for automation.[27:15 - 35:35] Practical Applications and Implementation StrategiesThey discuss specific areas where automation can be particularly effective, such as client onboarding.Utilize automation to streamline internal processes like reporting and communication.Korey explains the subscription model approach to make automation services more accessible.The group discusses the potential cost-effectiveness of automation compared to traditional solutions.[35:36 - 44:06] Long-term Benefits and Final ThoughtsPenny and Damien reflect on how automation can free up mental space for firm owners and employees.Regularly review and update processes to maintain efficiency and effectiveness.The value of combining process improvement, outsourcing, and automation strategies.Invest in automation as a long-term solution for firm growth and employee satisfaction.Direct Quotes "Before we even start development or anything, we'll spend a few hours with firms and like help them map and document and understand like what automations are going to be realistic." –  Korey Cournoyer"I think standardization is the first step to becoming flexible." - Penny BreslinConnect with KoreyWebsite: http://strms.io/Company Linkedin: https://www.linkedin.com/company/strms-automationsPersonal Linkedin: https://www.linkedin.com/in/koreycournoyer/-----------------------------------------------------------------------------Thank you for listening. Please like and share this episode with a friend!Websites: https://moneypennyllc.com/LinkedIn: https://www.linkedin.com/in/damiengreathead/Twitter: @Damien_GHLinkedIn: https://www.linkedin.com/in/penny-breslin-0228b81/Twitter: @pennyb57

Are your accounting firm's processes truly optimized, or are you considering outsourcing as a quick fix to deeper workflow issues?In this episode, hosts Damien Greathead and Penny Breslin delve into the topic of outsourcing within the accounting industry. They discuss the challenges firms face with staffing shortages, the increasing client demand for accounting services, and the importance of having robust internal processes before considering outsourcing. The conversation highlights the need for clear communication, efficient workflows, and proper utilization of technology to ensure success. Penny emphasizes the significance of understanding why work is not getting done and addressing those issues internally before outsourcing.[00:00 - 10:00] Introduction and Staffing ChallengesDamien and Penny discuss the constant busy season in the accounting industry and the rising demand for outsourcing services.Understand the industry's current state and the increasing need for efficient processes.Penny discusses the high demand for remote workers and the increase in outsourcing booths at conferences.Competitive salaries and clear role definitions are crucial for attracting and retaining talent.[10:01 - 20:00] Client Demand, AI Impact, and Effective OutsourcingDamien and Penny explore the growing client demand for various accounting services, despite technological advancements.Emphasize the unique value and services your firm offers to differentiate from competitors.Identify and address internal workflow issues to ensure successful outsourcing.[20:01 - 30:00] Technology and Client CommunicationDamien and Penny discuss the role of technology in managing workflows and client expectations.Utilize technology efficiently and ensure clients are trained to use it properly.Penny shares experiences of managing client expectations and internal team coordination.Allocate responsibilities effectively within the team to maintain operational efficiency.[30:01 - 40:00] Reflecting on Processes and The Role of Internal TrainingPenny advises firms to revisit and optimize their processes, especially during slower periods.Regularly review and update processes to stay efficient and effective.The value of rephrasing questions is to understand and solve workflow issues better.Invest in training and clear communication to enhance team performance.Direct Quotes"If work isn't getting done for other reasons, outsourcing is the solution because the systems are working well, the teams and you want to grow." - Damien Greathead"You need to present a value to your clients and that you're worthwhile." - Penny Breslin"Before you outsource, make sure you're really good at what you do and your processes are standardized." - Damien Greathead-----------------------------------------------------------------------------Thank you for listening. Please like and share this episode with a friend!Websites: https://moneypennyllc.com/LinkedIn: https://www.linkedin.com/in/damiengreathead/Twitter: @Damien_GHLinkedIn: https://www.linkedin.com/in/penny-breslin-0228b81/Twitter: @pennyb57