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The Earmark Podcast

After 50 Years in Internal Audit, Richard Chambers Sees the Profession’s Greatest Risk Yet

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“Who’s going to provide the skepticism, the intellectual curiosity, and the institutional knowledge to our audit teams in ten years? Because the rest of us are going to be gone.”

Richard Chambers drops this stark warning after 50 years in internal audit. His concern isn’t about losing jobs to technology. It’s about the growing gap between how we’ve always trained auditors and what the profession now demands.

On this episode of the Earmark Podcast, host Blake Oliver sat down with Richard, Senior Advisor for Risk and Audit at AuditBoard. He brings a unique view of internal audit’s transformation. When he started in 1974, fresh out of college and working in a bank’s internal audit department, the job was all about checking financial records and looking backward. Today? Financial risks make up only 25% of audit plans. The rest involves cyber threats, AI governance, supply chain chaos, and what Richard calls “perma-crisis”—our new normal where tariff rates can change three times in a single day.

Most companies use AI, but only a quarter have set up proper governance over it, according to AuditBoard research. That gap presents massive risk and opportunity for internal auditors who can bridge it.

From Bean Counting to Risk Navigation

Internal audit has changed dramatically since Richard joined that bank in 1974. Back then, it was all ledgers and reconciliations—purely financial work focused on last year’s numbers. Today, financial risks are just a quarter of what internal auditors examine.

“The profession has matured,” Richard explains. “While we still do some work in the financial space, that’s really a small percentage of internal audit’s focus.”

The real game-changer has been what Richard calls “perma-crisis.” It started with the COVID-19 pandemic and hasn’t stopped. “We’ve been lurching from one risk-induced disruption to another,” he says, listing the cascade: pandemic, forty-year-high inflation, supply chain breakdowns, wars in Europe and the Middle East. “We’re in our sixth year of it, and I would submit this is the new normal.”

This constant chaos makes traditional planning almost useless. Richard found that nearly 60% of internal audit departments had already changed their 2025 plans by May. When tariff rates can swing wildly in a single day—Richard recalls hearing three different numbers from Washington in one day—annual planning is dangerous.

“You can no longer have any confidence that one scenario is the only one you have to worry about,” Richard emphasizes. Organizations need what he calls “scenario risk management,” or planning for multiple possible futures at once.

This need for flexibility shifts how internal audit works with other departments. The old model was called “three lines of defense”: management controlled risks (first line), oversight functions monitored them (second line), and internal audit was the last barrier before disaster (third line).

But pure defense isn’t enough anymore. In 2019, the Institute of Internal Auditors dropped “defense” from the name. The new message? “Independence does not mean isolation.”

Richard uses a ship analogy that really hits home. Organizations are like vessels at sea that need lookouts watching in all directions and talking to each other. “If your internal auditors are looking in one direction and your risk managers are looking in another,” he warns, “but they aren’t sharing what they’re seeing, then you don’t know whether there are gaps.”

AI: The Top Risk and Best Opportunity

Three years ago, AI wasn’t even on internal audit’s risk list. Today, it’s number one, pushing even the talent crisis to second place.

“Pre-2022, before ChatGPT came out, we weren’t asking about it,” Richard admits. Once he started surveying the profession, AI rocketed up the list: middle of the pack the first year, third place the next, then straight to number one.

This isn’t just another tech disruption. After watching five decades of change, Richard doesn’t mince words: “In the five decades I’ve been in internal audit, there’s never been a greater risk to this profession in terms of becoming irrelevant.”

The scariest part? When Richard asks why audit teams aren’t using AI more, the top answer is, “We don’t really understand it enough.” That hesitation could be fatal.

Yet Richard himself uses AI daily as his “research assistant.” He asks it to identify industry risks, outline articles, analyze data. “It takes me longer to write the prompts than it takes to give me the answer,” he notes.

The use cases are obvious and powerful. Risk assessments that used to happen annually can now be continuous. AI can scan for threats humans would never spot. Data analysis that took weeks happens in minutes. Even audit reports can be AI-generated.

But the trap is that AI excels at exactly the work that trains new auditors. Entry-level graduates traditionally learned by doing routine tasks. Now AI does those tasks better and faster.

“College graduates have traditionally been able to ease into professions by doing some of the more rudimentary tasks,” Richard explains. “But AI is prime for rudimentary tasks.”

This creates a vicious cycle. Companies hire fewer entry-level auditors. Without that pipeline, who develops the judgment for complex work? Richard’ solution: “We shouldn’t refrain from hiring them. We should be willing to bring them in and help them leap the learning curve.”

“AI won’t replace internal auditors,” Richard predicts, “but it will replace internal auditors who don’t use it.”

The Human Superpowers AI Can’t Touch

“To assess culture, you also have to be able to rely on your sense of smell.”

A chairman of the board of a large Indian company shared this wisdom with Richard years ago, and it perfectly captures what separates humans from AI. Technology can analyze documents and data. But it takes human instinct to sense what happens when nobody’s watching.

Richard identifies three “human superpowers” that AI cannot replicate: professional skepticism, intellectual curiosity, and relationship skills. These aren’t soft skills; they’re the core value of internal audit.

Take culture assessment. Richard has done two major research projects showing how toxic culture can destroy organizations. But judging culture requires reading between lines, sensing unspoken tensions, and understanding human motivations. As Blake pointed out during the conversation, “The body language, the way people talk to each other, all of that is context that AI just cannot have access to.”

The audit committee relationship shows this even more clearly. Richard chairs an audit committee and knows these relationships need more than data transfer. They require courage to “grab them by the face” and focus them on hidden risks.

“If we’re content to just answer the questions they ask,” Richard warns, “then we’re not really serving our organizations well. We have to help them understand the questions they need to be asking.”

This shift, from giving answers to finding the right questions, represents a huge evolution. While AI can list potential questions, there’s something fundamentally human about knowing which questions matter.

Most critically, Richard identifies one role that must stay human: assessing AI’s own governance. “I shudder to think that there may be a day where we ask AI to assess its own governance,” he says. “We would never do that with anyone else.”

The challenge is developing these human skills when the traditional path is disappearing. Without routine work to learn on, how do new auditors develop judgment?

We need to help new auditors develop skepticism, intellectual curiosity, and institutional knowledge from day one. Teach them to ask “why” before teaching them “how.”

As Richard reflects after 50 years, “What a difference from the bean counter view of internal audit. You get to be so curious as an internal auditor these days.”

The Next 50 Years Start Now

Richard’s journey from a bank to internal audit’s leading voice shows a profession that has transformed before and must do so again.

The collision of perma-crisis and AI doesn’t doom internal audit. It clarifies its purpose. When tariffs change three times daily, cyber threats evolve by the hour, and AI makes decisions we don’t fully understand, organizations desperately need professionals who ask the hard questions.

Not “What does the data say?” but “What isn’t the data telling us?” Not “How do we implement AI?” but “How do we govern what we can’t fully understand?”

The saying “independence does not mean isolation” applies to both organizational relationships and the human-AI partnership. Tomorrow’s successful auditors won’t resist AI or surrender to it. They’ll orchestrate a sophisticated dance between computational power and human intuition.

The fact that entry-level work is vanishing while judgment becomes more critical demands new thinking about professional development. Organizations can’t wait for fully-formed auditors. They must cultivate intellectual curiosity from day one.

For accounting and tax professionals watching internal audit’s future, Richard warns those who avoid or fear AI will become irrelevant. But he also extends an invitation: those who combine technology with human capabilities will find themselves at the center of organizational decision-making.

Listen to the complete conversation to understand why this moment represents internal audit’s greatest challenge and its most exciting opportunity. After five decades in the profession, Richard reminds us the question isn’t whether internal audit will survive the age of AI. It’s whether individual auditors will choose to evolve with it.

From Random Acts of Advisory to Strategic CFO Services

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“The darkest times for an industry are the times in which an accountant is most valuable.”

Chris Macksey, CEO of Prix Fixe Accounting, learned this firsthand during the COVID-19 pandemic. While restaurants nationwide struggled to survive, his specialized firm actually grew—not despite the crisis, but because of it. Restaurant owners desperately needed help navigating Paycheck Protection Program (PPP) loans, Economic Injury Disaster Loan (EIDL) applications, and industry-specific relief programs that their generalist accountants couldn’t handle.

In this live recording of the Earmark Podcast from Boston’s Advisory Amplified tour, host Blake Oliver explores how accounting firms can evolve beyond traditional services to become true strategic partners. Joined by Chris and James Erving, Head of Sales, Americas at Fathom, the conversation shows that delivering valuable advisory work doesn’t require advanced certifications or complex methodologies. It just takes a willingness to form opinions and use modern tools to turn financial data into business guidance.

What Advisory Really Means (And Why Accountants Struggle With It)

The accounting profession can’t even agree on what advisory means. James cuts through the confusion with a simple definition: “Being involved in the decision-making process rather than just the delivery of information.”

Chris takes it further. At Prix Fixe Accounting, he treats advisory as completely separate from Client Accounting Services (CAS), even assigning different team members to each. “It’s any of the work that you can’t scope really very easily,” he explains. Unlike predictable bookkeeping tasks, advisory demands flexibility and judgment.

The real challenge is having an opinion. “I have run into so many accountants who just won’t have an opinion about anything other than the accuracy of the financial statements,” Blake says bluntly.

Chris shows what having an opinion looks like in practice. When a restaurant’s food costs creep up from 23% to 28%, he doesn’t just report the variance. He digs deeper. “Is it that something’s changed in the kitchen, or is it just inflation that’s causing that number to gradually rise over time?” That shift from reporting what happened to explaining why it happened (and what might happen next) is where advisory begins.

But not every client needs this level of service, and knowing when to offer it makes all the difference.

Finding the Right Clients for Advisory Services

James identifies three clear signals that a business needs advisory support. First, rapid growth that outpaces the owner’s ability to manage finances. Second, reaching a size where DIY financial management becomes overwhelming but hiring a full-time CFO doesn’t make sense. Third, major events like acquisitions or exit planning.

This targeted approach beats what James calls “random acts of advisory”—the unpaid, unstructured advice many firms already provide without recognizing its value. By identifying specific triggers, firms can systematically deliver advisory services rather than hoping opportunities appear.

The conversation also reveals an important distinction between types of forecasting. James explains that small businesses often need short-term cash flow forecasts to predict cash positions in the next week or two. Larger or more stable businesses benefit from FP&A-style planning with three-to-12-month horizons and scenario modeling.

Understanding which clients need which services allows firms to focus their efforts where they’ll have the most impact, and where clients see enough value to pay premium fees.

Why Industry Specialization Accelerates Advisory Success

Chris’s restaurant-only focus demonstrates the power of specialization. His firm doesn’t just understand debits and credits; they understand why champagne and caviar became popular during the pandemic, how street construction affects revenue, and when consumers will pay for fine dining versus seeking value menus.

“Right now, consumers really feel a lot of pain in the pocketbook,” Chris explains. “The auto loan default rate is up. Credit card balances among consumers are at their highest levels. Consumer confidence is down.” This economic insight shapes his current advice: forget the $175 prix fixe menu and focus on feeding a family of four for under $75.

The specialization advantage goes beyond knowledge. Chris spent over a decade as a chef before becoming an accountant. “It’s a little bit of a cult industry,” he says of restaurants. “If you’re in, you’re in. If you’re out, you’re out.” This insider status builds trust that no amount of technical expertise could match.

His firm even mandates their approach. “The tech stack is set. There really aren’t any options. And there’s only one price point, it’s prix fixe. And you’re just going to have to enjoy the ride.”

This confidence comes from aggregated data across similar businesses. When restaurants see sales drop 20%, Chris can show clients it’s an industry-wide trend, not a personal failure. “When you can actually see that data and validate it for yourself, you know that no, it’s not you. It’s just the economy.”

The depth of specialization creates value generalist firms can’t match, but you don’t need a decade of industry experience to start delivering meaningful advisory services.

Making Advisory Practical: Tools, Metrics, and First Steps

“Once they actually do it for the first time, they realize, oh, I’m just looking at the last three years. I’m kind of rolling it forward, making an educated guess on what it’s going to be. And that’s really all it is.”

Chris uses this approach to explain forecasting for his team. Rather than treating it as an advanced skill only partners can handle, he involves staff accountants in creating annual budgets. They examine historical data, consider market conditions, gather client insights, like upcoming construction that might impact foot traffic, then make informed projections.

The key is matching the service to the business reality. Chris doesn’t do detailed cash flow forecasts for restaurants because “they have such tight cash flow that you’re off 5% and your cash flow projection’s shot.” Instead, he focuses on annual budgets with monthly check-ins.

Visual presentation transforms complex data into insights clients can actually use. “Our client base is largely visual people, and the financial literacy is usually pretty low,” Chris notes. He spent over a decade cooking before seeing a P&L statement, so he understands the challenge. Charts showing 12-month trends for metrics like food costs communicate far better than spreadsheets full of numbers.

Non-financial metrics add crucial context. For lodging clients, Chris tracks occupancy rates, average daily rates, and rooms sold. These are “numbers that you will not see surfaced in QuickBooks.” When revenue changes, these metrics reveal whether it’s a pricing issue or a volume problem.

James emphasizes the importance of using proper tools. “You don’t have to build an entire Excel model customized to a client to get started.” Modern platforms like Fathom automate much of the work, creating professional forecasts and visual dashboards without custom spreadsheets for each client.

For firms ready to begin, Chris and James offer practical advice. Start with forecasting, since it’s a natural extension of work you already do. Pick one or two industries where you have multiple clients and build expertise gradually. Ask more questions about your clients’ businesses. And remember, clients don’t expect you to know everything. They value accountants willing to connect financial data to business decisions.

Your Path from Compliance to Advisory

The shift from traditional accounting to advisory starts with three elements: forming opinions based on financial data, developing knowledge of specific industries or situations, and using modern tools to make forecasting efficient rather than overwhelming.

Chris’s experience during the pandemic proves the value of this transformation. While generalist firms struggled to help clients navigate crisis programs, his specialized knowledge made Prix Fixe Accounting indispensable.

The firms making this transition today position themselves for a future where their value only increases. Economic uncertainty creates more need for strategic guidance. Industry disruption demands advisors who understand both the numbers and their context. Business owners facing unprecedented challenges need professionals willing to venture beyond historical facts into forward-looking advice.

Listen to the full episode to hear additional insights on pricing advisory services, overcoming staff resistance, and managing the cultural shift within your firm. Chris and James’s conversation offers a practical roadmap for any firm ready to move beyond “random acts of advisory” to systematic, profitable guidance that transforms both your practice and your clients’ businesses.

Smart Accounting Firms Are Done Being Yes People

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Picture an  accounting firm that keeps partner salaries locked away like state secrets. Staff spend years wondering what partnership actually pays. Meanwhile, another firm down the street posts everyone’s salary on a public leaderboard. The path to partnership comes with clear milestones and transparent rewards.

This stark difference shows just one way “renegade” firms are shaking up the accounting profession.

In episode 104 of the Earmark Podcast, recorded live during the Advisory Amplified tour in Austin, host Blake Oliver digs into what it means to be a “renegade” in accounting. He’s joined by Madeline Reeves, founder and CEO of Fearless Foundry, and Wesley McDonald, go-to-market leader at Relay. Together, they explore how forward-thinking firms and tech companies challenge everything we thought we knew about running an accounting practice.

What Makes a Firm “Renegade”?

So what exactly is a renegade firm? Reeves has worked with many of them, and she has a clear answer.

“A renegade firm is leading their clients to somewhere new and is not settling for the ways things have always been done,” she explains. These firms challenge the status quo. They see tech companies as partners, not just vendors. And they push their clients and technology partners to do better.

These firms also stand out in unexpected ways. Take Lance CPA (now part of Revel CPA). When they signed new clients in the brewery and hospitality space, they didn’t just send a standard engagement letter. They delivered beautiful welcome kits complete with custom beer glasses and cool socks. It was their way of saying this isn’t your typical accounting relationship.

But being a renegade goes deeper than nice gestures. These firms also excel at saying no.

“A lot of firms are dedicated to being acts-of-service people,” Reeves notes. “They become a little bit of “yes people” or people pleasers. But the real renegade firms are like, ‘I do not do that service or I do not work with that industry.’”

They’re not trying to be everything to everyone. They focus on being exceptional at what they do best.

Taking the Lead with Clients

Traditional firms often let clients call the shots. They use whatever software the client prefers. They adapt to the client’s processes. They follow rather than lead.

Renegade firms flip this completely around.

Reeves puts it perfectly: “When I go to the dentist, I’m not telling the dentist, ‘No, don’t use that drill in my mouth.’ I don’t know how to do dentistry. So if you’re an accountant, it’s your job to lead your clients.”

These firms come to the table saying, “This is how we do this job well and effectively for you. If the goal is advisory services, this is how we get there better, faster.”

When you’re the professional, you set the standards for how the work gets done.

Breaking Open the Black Box of Compensation

One radical change happening in renegade firms involves money—specifically, who knows what about everyone’s pay.

“On the most successful sales teams I’ve been a part of, there’s a leaderboard that shows exactly how much people have attained in their salary in that quarter,” McDonald shares. “Which is a wild concept to think about in some industries.”

Oliver points out the obvious problem with traditional secrecy: “One of the biggest secrets is how much the partners make. But if we want everybody to want to be a partner, why don’t we tell them?”

It’s not just about knowing the numbers, though. Reeves emphasizes that firms need “not just pay transparency but pathway transparency.” People need to see the clear steps to advancement, not just the end goal.

McDonald, drawing from his tech experience, says promotions shouldn’t be about time in seat. “You’re ready to move to the next level as soon as you’re performing at that level.”

This represents a huge shift from the traditional model where you might wait five years for a promotion regardless of your performance.

Building Teams That Actually Want to Work Together

The old model pits high performers against each other. Remember those weekly emails showing who billed the most hours? Competition is the traditional way to drive performance.

Renegade firms take a different approach.

“If you have people on your team who think the only way up is their own performance, your whole team is going to be fighting against each other,” Reeves explains. She learned this building sales teams. When she tied part of compensation to team performance, not just individual metrics, “We saw performance double because people were suddenly willing to turn to the teammate next to them and show them what was working.”

This collaborative approach is essential for attracting younger professionals. As Reeves notes, “There are a lot of young people who are coming out of school, and there’s nothing exciting to them about working 90 hours a week during tax season. They’re like, ‘hard pass.’”

“You can tell people to do the work and you can pay people to do the work,” Reeves says. “But to actually get people to want to show up and fully do the work, it has to align around the things that genuinely motivate them as a human.”

When Banking Becomes a Partnership

Banking isn’t usually seen as innovative. But companies like Relay are changing that, starting with how they work with accountants.

Most people choose banks for passive reasons. “It’s because I know that bank exists or they’re down the street or my parents bank there,” McDonald observes.

But what if your bank actually worked for you and your accountant?

“Relay is purpose built for our accounting partners and their clients,” McDonald explains. Traditional banks gatekeep information. Relay surfaces it to accountants so they can actually help their clients.

The difference is stark. “I’m not even sure how I would give feedback to Chase or Bank of America or Wells Fargo,” Oliver admits. In contrast, McDonald says, “If a partner of ours has an idea and they bring it to us, we will act on that idea.”

This isn’t just talk. Being a champion for SMEs and their partners is one of Relay’s seven core values. They were the first banking platform to go to market specifically through accounting professionals.

Reeves shares her own frustration with traditional banking. She wanted to support a local community bank that shared her values. But they had no online banking. Getting statements required writing emails to a banker.

“If you’re really serving small business at the core of who you are,” she says, “making me have to email a banker to get a bank statement isn’t serving small business. That’s creating extra manual work for me or for my accountant.”

Learning from Renegade Mistakes

Being a renegade means trying new things. And that means making mistakes.

Reeves shares a particularly painful one. She built what she thought was an innovative compensation model, paying top performers a percentage of deals they closed. Then she discovered a senior employee was committing fraud, jacking up prices in their proposal system to increase her cut.

Reeves recalls discovering the fraud just before a major conference and having to lock down all her banking immediately. The experience taught her to “trust but verify.” You need systems to ensure people act the right way, even those you trust.

McDonald shares his own revelation about breaking from the traditional path. He started his career as a fixed income broker. But as he earned promotions, he looked around and realized, “everyone there had been doing it for 30 years. I thought, ‘Can I do this for 25 more years?’”

He chose the non-linear path instead, moving between sales, consulting, and building teams. “I had stopped my learning journey,” he reflects. “I want to be a lifelong learner.”

Oliver’s “mistake” was majoring in music at the most expensive university in the country. But the experience taught him how to teach himself anything—a skill that proved invaluable in accounting. “If you can sit in a practice room for six hours a day and learn how to play a concerto, that’s all just breaking problems down into literally measure by measure, note by note.”

The Path Forward

The renegade firms discussed in this episode aren’t making small tweaks to the traditional model. They’re rebuilding it from scratch.

They’re becoming strategic leaders who guide rather than follow clients, creating transparent cultures where collaboration beats competition, and embracing technology companies as true partners rather than necessary evils.

With younger professionals rejecting traditional firm culture and clients demanding strategic guidance over compliance work, the old model is dying. The renegade approach offers a sustainable alternative that actually addresses why people leave accounting.

These innovations are happening right now at thriving firms. From brewery-themed welcome kits to banking platforms built for accountant collaboration, these changes prove accounting firms can create experiences that rival any modern service business.

Want to hear the complete conversation? Listen to the full episode. You’ll get the full story of how Reeves uncovered fraud through her proposal system, Olivers’s journey from professional musician to accounting innovator, and detailed strategies for implementing renegade principles in your own firm.

The Accounting Platform That Achieves 96.5% Automation Reveals How They Did It

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“No one’s going to be outcompeted by the AI itself. You are going to be outcompeted by firms that really adopt this aggressively,” warns Jeff Seibert, whose company just hit 96.5% accuracy in automated bookkeeping—something that seemed impossible just a few years ago.

In this milestone 100th episode of the Earmark Podcast, Blake Oliver sits down with Jeff Seibert, co-founder and CEO of Digits, to explore how AI is fundamentally changing the architecture of accounting software. Seibert brings fresh eyes to accounting—he previously led consumer product at Twitter and built Crashlytics (now running on six billion smartphones). His frustration was simple: Why could product teams access real-time analytics while business owners waited weeks for black-and-white spreadsheets?

Founded in 2018, Digits set out to reimagine accounting in the age of machine learning. While traditional software treats transactions as meaningless text in rigid databases, Digits achieves near-perfect automation by treating financial data as interconnected objects that learn from patterns across millions of transactions.

The 30-Year-Old Problem Holding Back Accounting

As Seibert sees it, the fundamental issue facing bookkeeping automation is that every major accounting platform—QuickBooks, Xero, and even NetSuite—runs on relational databases designed 20-30 years ago. These systems treat transactions as simple text entries with no understanding of what they mean.

“QuickBooks is just going to see an Uber transaction as “U-b-e-r”. It just sees text,” Seibert explains. “It doesn’t understand the data, it doesn’t know what Uber actually is.”

This limitation explains why Intuit, with all its resources, has yet to deliver meaningful automation. The answer is architectural. Each QuickBooks company exists in its own isolated database, preventing the software from learning patterns across businesses. The constraints run so deep that QuickBooks still can’t handle having a vendor and customer with the same name—it appears they chose “name” as the primary database key decades ago.

Digits takes a completely different approach using what’s called a vector graph data model. Everything becomes an object—Uber is an object, your expense categories are objects, your bank accounts are objects. Transactions become connections between these objects, creating a web of financial relationships the AI can understand.

This mirrors how large language models (LLMs) work, converting transactions into vector embeddings, essentially plotting them in multi-dimensional space where similar items cluster together. When trained on 170 million transactions representing nearly $1 trillion in business activity, patterns emerge that would be obvious to humans but invisible to traditional software.

“When you have that scale of data and you see how everyone has booked Uber before, you start to see patterns,” Seibert notes. “The model starts learning. If it sees Lyft in your accounting for this client, it then knows how to book Uber.”

How AI Agents Actually Work (Hint: Like Clever Interns)

The accounting world is buzzing about “AI agents,” but what are they really? Seibert explains, “An agent is simply an LLM that you run in a loop. You give it a task, it attempts the task, you ask if it completed it. If not, it continues until it’s done.”

Think of them as clever interns who never get tired. Digits has been running these agents in production since January 2024, primarily for researching unfamiliar transactions.

The system uses three layers of intelligence. First, it checks if this specific client has seen this transaction before. If yes, it books the transaction exactly the same way. Second, if the transaction is new to this client but familiar to the platform, it uses its global model trained across all users. Third, for completely novel transactions, the agent literally Googles them.

“What would you do as an accountant? You would probably Google it,” Seibert explains. “What do our agents do? They literally Google it, research the transaction, build a dossier about it.”

As a result, only 4-5% of transactions now require human review, compared to the 20% that typically slip through even well-maintained rule-based systems. Notably, the system maintains strict confidence thresholds. Any transaction it is unsure about gets flagged for human review. It never guesses when uncertain.

The upcoming reconciliation feature shows how sophisticated these agents have become. The system pulls statements directly from banks or extracts them from PDFs, then matches transactions with pixel-level precision. “You can literally click on the transaction and see it on the statement and vice versa,” Seibert says. This builds trust with accountants who need to see exactly where the numbers come from.

What This Means for Your Firm’s Future

As of August, Digits hit 96.5% accuracy, up from 93.5% in spring. Each percentage point represents thousands of transactions that no longer need human touch. But it begs the question: how do you price services when the work happens automatically?

“If you’re charging purely per hour right now, then automation may make that challenging,” Seibert acknowledges. But forward-thinking firms are already adapting. They’re moving to fixed-fee models for routine work like monthly closes, which become increasingly profitable as automation reduces time investment. Many use a hybrid approach, charging fixed fees for the close, and hourly rates for advisory work.

At a flat $100 per month (with volume discounts for accounting partners), Digits offers predictable pricing that contrasts sharply with QuickBooks’ constant increases. The platform even offers specialized SKUs for ledger-only or reporting-only clients, accommodating diverse practice needs.

The staffing implications are real but not apocalyptic. Junior bookkeeping roles focused on data entry will diminish. But Seibert points out this could make the profession more attractive: “You don’t want to just sit there doing data entry all day long. You want to learn how to advise businesses.”

Seibert recommends firms start small when implementing automated bookkeeping. “Pick one client in your firm and see what you can achieve,” Seibert challenges. Choose a simple, digital-native business like consultants, SaaS companies, or agencies with predictable electronic expenses. Build confidence, then expand to complex cases.

Building Trust Through Transparency

With financial data flowing through AI systems, security is crucial. Digits addresses this with architecture developed at Seibert’s previous companies, where they handled crash data from billions of smartphones.

Everything stays within Digits’ systems; they don’t send raw data to OpenAI or other third parties. All data is encrypted at rest using per-object envelope encryption, where each object has its own encryption key. Even if breached, stealing one key wouldn’t compromise the system.

The platform is SOC 2 Type 2 certified, with complete audit trails showing who changed what and when. You can even grant granular access, like giving your marketing manager visibility into only marketing expenses. “They can see marketing, all the transactions booked to marketing, and nothing else,” Seibert explains.

Importantly, when AI does the work, you can trace exactly what happened. Click on any transaction to see the activity log. This solves the common problem of clients making changes in QuickBooks without anyone knowing.

The Competitive Reality Check

Seibert’s warning deserves repeating: “No one’s going to be outcompeted by the AI itself. You are going to be outcompeted by firms that really adopt this aggressively.”

This isn’t hypothetical. Firms using advanced automation already serve more clients with similar-size teams, offer competitive pricing while maintaining margins, and provide real-time insights that clients increasingly expect.

You don’t have to become a tech expert. Set aside time each month after the close to try new tools. Watch YouTube videos about AI agents (though Oliver warns to avoid the hype channels). Most importantly, maintain healthy skepticism. As Seibert notes about AI doing math, “If it’s not 100% correct, what’s the point?”

Remember, AI agents are like clever interns. They’re eager, overconfident, and need supervision. They excel at tedious, repetitive tasks but need human judgment for nuanced decisions. The goal isn’t to replace accountants but to eliminate the work accountants wish they didn’t have to do.

Taking the First Step

Thoughtfully evaluate how these innovations can augment your practice. Start with one simple client. See what 96.5% automation actually feels like. Build confidence, then expand gradually.

Listen to the full episode to hear Seibert’s complete vision and practical guidance on everything from selecting pilot clients to restructuring pricing models. The tools to eliminate tedium while amplifying expertise aren’t coming; they’re here, proven, and improving rapidly. How quickly and thoughtfully can you integrate it?

Your Team Actually Wants You Less Involved in Daily Operations—Here’s How to Give Them What They Need

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For an accounting firm owner, days can feel like an endless stream of Slack notifications and “quick questions” from your team. You’ve become your company’s “internal Wikipedia”—the go-to source for every operational decision, client question, and process clarification. Sound familiar?

Chase Damiano, founder of Human at Scale and recent guest on the Earmark Podcast, has a name for this trap: the bottleneck.

Damiano brings a unique perspective to the accounting world. After scaling Commonwealth Joe Coffee Roasters from zero to $5 million in revenue and earning a spot on Forbes’ 30 Under 30 list in 2018, he experienced burnout so severe it drove him to take a 12-week sabbatical that included two weeks of silent meditation. This radical reset transformed his understanding of leadership and delegation. Now, he shares those insights with accounting firm leaders trapped in similar operational quicksand.

In his conversation with host Blake Oliver on the Earmark Podcast, Damiano challenges a fundamental assumption plaguing firm owners: the belief that hiring more people will solve their capacity problems. The reality is far more complex. Breaking free requires a systematic approach to delegation that transforms how you communicate expectations and how you measure success.

Every overwhelmed firm owner needs to understand three critical transformations. First, why the traits that make you successful—perfectionism and desire to serve—become the quicksand that traps you. Second, how a six-part delegation framework frees you from daily firefighting. And third, why building a “team responsibility inventory” provides the roadmap for extracting yourself from workflows while actually increasing your team’s autonomy.

The Psychology of Being Stuck: Why Good Intentions Create Bad Systems

Before you can implement systematic delegation, you need to recognize that the very traits that made you successful now hold your firm hostage.

Damiano knows this pattern intimately. After scaling his coffee company to $5 million in revenue, he found himself addicted to the productivity habit. It took three full weeks of his sabbatical just to stop compulsively “figuring things out.”

“Even the act of ‘figuring out your life’ can now look more like a job,” he explained to Oliver. “Wake up, have breakfast, go to a coffee shop to figure things out. Then it’s time for lunch, more figuring out, dinner—and suddenly another day has vanished.”

This addiction to busyness hits accounting firm owners particularly hard. Your perfectionism, your genuine desire to serve clients, and your technical expertise aren’t character flaws. They’re the foundation of your professional success. But when it comes to scaling a firm, they become quicksand.

Oliver admits he fell into this exact trap with his own firm. “I said yes to everything,” he reflected during the conversation, “and then I’ve got too much to do and I’m busy all the time, working 60 hour weeks.”

The desire to help everyone feels noble in the moment. But it creates a system where your brain becomes the firm’s operating system. Every decision, every quality check, every client question routes through you.

The perfectionism problem runs deeper than just workload. Oliver shared an example from his time at a Big Four firm. The nonprofit team was performing full compilation engagements for clients who didn’t need them. “Most of these nonprofits did not need compilations, but we were doing it anyway with a huge added cost,” he observed. The team could have delivered a simpler service at better margins while still meeting client needs.

Damiano challenges firm owners to examine their “inner data”—not financial metrics, but the intuitive signals about energy and alignment. When he asks bottlenecked CEOs how they feel day-to-day, the answer is always the same: “incredibly draining,” “incredibly stressed,” “I don’t want to do this.”

Yet the pattern continues. They know they’re stuck, they can articulate the problem, but they take no action to change it.

This paralysis stems from a fundamental identity crisis. As Damiano discovered after exiting his coffee company, entrepreneurs often don’t know who they are without their business. “Everyone asked me what I’m going to get into next.” he recalled. “People assume you’re going to go on to an even greater thing, but you might not be clear about that internally, and that’s okay.”

The reality check comes when you realize your team actually wants you less involved. Teams see your pain from being overwhelmed. But more importantly, they experience frustration when you inject yourself into processes and “muck things up,” as Damiano puts it.

Your team craves autonomy over their roles. They want to make decisions without running everything by you. But first, you need to accept that your five-minute solution might be worth sacrificing for their two-hour learning experience.

Damiano’s perspective on one-on-ones captures the mindset shift required: “Your one-on-ones should not be about status updates. It’s an opportunity to develop them as leaders in every role, in every position. They should do 80 plus percent of the talking.”

Understanding these psychological barriers is crucial, but awareness alone won’t free you from the trap. You need a concrete system for transferring responsibilities that addresses both your need for quality and your team’s need for clarity.

The Six-Part Delegation Framework: From Chaos to Clarity

The breakthrough moment in Oliver and Damiano’s conversation came when Oliver realized effective delegation to humans uses the exact same structure as prompt engineering for AI.

“What you just described is a well-written prompt,” Oliver exclaimed as Damiano outlined his delegation system. “It’s the same thing.”

This revelation transforms delegation from an art into a science. The framework emerged from Damiano’s observation of countless delegation failures. One particularly instructive disaster involved a chief operating officer who attempted to delegate a billing process. She wrote just seven words on a piece of paper: “Manage billing process while I’m out on vacation.”

The predictable result? Complete failure. Without context, success criteria, or clear boundaries, the delegation was doomed from the start.

During the podcast, Damiano and Oliver worked through a real example: delegating the management of weekly team meetings. Here’s how the framework transformed this common bottleneck into a clear, delegatable responsibility:

1. Name the responsibility: “Manage and coordinate weekly team sync.” Just two to three sentences that start with action verbs.

2. Define the purpose: As Oliver articulated: “Our weekly team sync is what keeps everyone organized and makes sure nothing falls through the cracks. It helps us prioritize.” Damiano added, “This is our command center for what is happening for the week, but also a place for us to come together as a culture.”

3. Establish success metrics: “Everybody leaves the meeting with their top three to five priorities clearly defined. We’ve addressed any blockers,” Oliver said. Plus the binary metric: Did the meeting happen? Did everyone who could attend actually attend?

4. Document the process: They mapped out everything from sending meeting invites and creating agendas to collecting topics, facilitating discussions, and updating the practice management system.

5. Identify resources: Access to calendars, ability to run reports on upcoming deadlines, time for preparation and follow-up. “In a prompt that would be the tools,” Oliver noted.

6. Clarify decisions: The operations manager can choose meeting times and create agendas autonomously, but needs approval to cancel meetings two weeks in a row.

The elegance of this system lies in its flexibility. “Those first three are perfect delegation opportunities for a more senior individual,” Damiano explains. Junior team members benefit from all six elements as guardrails.

What makes this framework powerful is how it addresses trust issues that sabotage most delegation attempts. When delegation fails using this structure, you can pinpoint exactly what went wrong.

“You can literally look at it and pinpoint exactly where,” Damiano says. “And that is what makes the delegation stick, because you can just fix that one issue.”

The framework also flips the traditional delegation dynamic. Instead of the owner having to document everything, team members can use these six elements as a guide to ask better questions. This transforms delegation from a top-down directive into a collaborative process.

Oliver’s enthusiasm was immediate: “I’m going to start using this. I’m going to do this tomorrow with my team.”

The framework addresses his core challenge: getting his team to take ownership without constantly coming to him for decisions. By clearly defining decision boundaries upfront, team members gain confidence to act autonomously while knowing exactly when to escalate.

But individual delegation is just the beginning. True transformation requires examining every responsibility across the entire firm.

Building Your Delegation Roadmap: The Path to Strategic Leadership

Moving from technician to strategic architect demands a systematic inventory and redistribution of all responsibilities across your firm.

Damiano calls this process building a “Team Responsibility Inventory.” As Oliver discovered with his own 16-person company, you can reach a point where founders are still doing work from when the company was half its size.

“We’re the bottleneck,” he admitted, recognizing how he and his partner had become “functionally critical participants in the workflow” even though they now had a team capable of handling that work.

The Team Responsibility Inventory begins with radical transparency. Every team member completes a seven-day time audit, brain-dumping every task and responsibility they handle. No organization needed, just raw data.

Then comes the revolutionary part: a facilitated session to compile all these responsibilities and review them line by line as a company. For many firms, this marks the first time the team sees exactly what’s on the CEO’s plate.

“Imagine you’re going line by line through these responsibilities and as a team making a decision,” Damiano explains. “Should the CEO still have this responsibility?”

The power of this collective review can’t be overstated. Team members who’ve been frustrated by their CEO’s constant intervention suddenly understand the impossible workload their leader carries. More importantly, they become active participants in solving the problem.

Each responsibility faces one of six possible destinies: hire someone, delegate and train internally, outsource to a service provider, automate through software, consciously eliminate, or keep.

The elimination option deserves special attention. “This is an underused one,” Damiano emphasizes. After years of growth, firms accumulate zombie tasks—reports nobody reads, processes that served a purpose five years ago.

Oliver shared the perfect example: “There’s all these people running weekly, monthly, quarterly reports that were defined five years ago that they’ve been sending out constantly and nobody’s actually reading them.”

The delegation roadmap shows how responsibilities shifts over time. But successful execution requires developing your team’s decision-making capabilities, not just their technical skills.

This is where Damiano’s “Problem-Outcome-Solution Framework” comes in. Instead of bringing problems to leadership, team members learn to present complete proposals. Define the problem and its cost. Articulate the desired outcome. Recommend a solution with clear resource requirements.

Oliver’s current challenge illustrates why this matters: “My team comes to me with a problem and then I have to use my brain space to think about the solution. But it’d be much better if they defined the problem, defined the outcome they want, and gave me a proposed solution.”

This shift transforms every interaction from a drain on the CEO’s cognitive resources into a development opportunity for the team member.

The framework works because it addresses a fundamental misunderstanding about delegation. Firm owners often justify keeping tasks because “I could do this in five minutes. Why delegate something that takes them two hours?”

But this calculation ignores the compound effect. That two-hour learning investment today becomes 90 minutes next week, then 60 minutes, then eventually faster than you could do it yourself—all while freeing you to focus on strategic work only you can do.

Oliver’s ultimate success story proves what’s possible. After five years building his firm with these principles, he achieved the dream: “I was doing no sales, I was doing no client work. We were getting customers. They were getting served. They were happy, they were paying. Money was coming into the bank and I was not involved.”

For anyone trapped in 60-hour weeks, Oliver’s enthusiasm is infectious: “I will tell you that it is the greatest thing in the world to get into that position, because then you’re really just an owner of a business.”

From Bottleneck to Breakthrough: Your Next Strategic Move

The journey from bottleneck to strategic leader is about fundamentally reimagining how knowledge and decision-making flow through your organization.

Damiano’s framework reveals that delegation isn’t a single skill but a system. It requires clear communication, defined success metrics, and the courage to accept “good enough” from others. The same perfectionism that built your reputation can become the cage that limits your growth.

This transformation extends beyond individual firms to the entire accounting profession’s evolution. As AI handles increasingly complex technical work, the firms that thrive will be those where owners have already extracted themselves from technical execution. They’ll focus on strategy, relationships, and innovation instead.

What makes Human at Scale different is, “We don’t just come in as a consultant or advisor or coach,” Damiano explains. “We actually come in and join your team. We are in there, actually running these systems and building that with you.”

Listen to the full conversation between Oliver and Damiano on the Earmark Podcast to discover additional frameworks and tools. Visit Human at Scale to take their operational leadership assessment that can diagnose your firm’s specific bottlenecks.