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Blake Oliver

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?

How One CPA’s Personal Software Solution Became the Answer for Firms of Every Size

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Tim Sines, CPA, has been practicing accounting for 38 years. During that time, he tried “pretty much all” the practice management software platforms available, but nothing worked the way he wanted. So he did what any developer would do: He built his own.

What started as a personal solution evolved into Mango Practice Management, a cloud-based platform that now serves everyone from solo practitioners to firms with over 100 employees. During a recent Earmark Expo demonstration, Sines walked through the system he’s been perfecting since the DOS era, showing how it addresses the core challenge facing most accounting firms: managing multiple disconnected systems.

The Problem with Disconnected Systems

Sines didn’t set out to revolutionize practice management. He just wanted software that actually worked for his practice. After years of frustration with existing tools, he developed his own application. The system has evolved dramatically over the decades, progressing from DOS to Windows desktop to its current cloud-based form, which has been running for over eight years.

Mango Practice Management handles time tracking, invoicing, electronic payments, project management, engagement letters, budgeting, and reporting. “Those are really the core things you’re doing daily within your firm,” Sines explains. The problem wasn’t that these functions were too complex. It was that they existed in separate systems, creating inefficiency at every step.

During his demonstration, Sines shows how Mango handles time entry in a way that connects directly to other functions. Users start typing any part of a client name, and the system automatically brings up relevant engagements. Whether you’re doing tax planning or tax prep, the system handles billing increments and supports multiple concurrent timers. The time flows directly into invoicing without requiring users to switch systems or re-enter data.

The integration is especially valuable when corrections are needed. As Sines notes, staff “notoriously record time to the wrong engagement or wrong client.” Instead of forcing users to exit invoicing, navigate to time tracking, make corrections, and start over, Mango allows these fixes right in the invoicing interface. Users can move time between clients or engagements and see write-ups and write-downs in real time.

Streamlined Client Payments and Communication

The platform extends its integration approach to client interactions, particularly around payments. Traditional practice management often treats payment collection as an afterthought, requiring clients to navigate separate portals or remember login credentials.

Mango embeds payment functionality directly into client communications. When clients receive an invoice, they see a “click to pay” button. “The client does not have to log into a client portal to make a payment,” Sines explains. If they’ve entered payment information before, the system displays the last four digits for easy recognition.

The integration goes deeper with engagement letters. When a client agrees to recurring services and signs electronically, the system automatically sets up the entire payment infrastructure. It creates recurring invoices, establishes payment schedules, and collects payments on agreed-upon dates. Sines calls this “invoicing on autopilot,” noting that some firms have “100 or more of these set up” and “don’t even have to do the invoicing.”

Document management follows the same seamless approach. Using Outlook and Gmail plugins, accountants can send document requests through simple email links. When clients click the link, their uploads automatically route to the correct engagement folder. “You don’t have to log into the portal,” Sines explains. “In that email, there’s a link. Click it, and you’ll be redirected to a screen. You just drag and drop your documents.”

The system also handles collections automatically. It monitors payment terms and sends statement reminders without human intervention. “Mango will go do these statements automatically in the middle of the night” for any client with overdue invoices, with customizable follow-up intervals.

Project Management That Connects Everything

Many practice management tools treat project tracking as a separate feature. Mango makes it central to firm operations. The project management dashboard shows projects due this week, next week, and overdue items, connecting these deadlines to internal workflows and capacity.

A key feature is what Sines calls “complete tasks in order” functionality. This prevents team members from jumping ahead in workflows. “I can’t review the tax return until I’ve done the tax prep,” he explains. This ensures that “staff focus on what is in the batter’s box, not what’s on deck.”

The system addresses a common problem: showing people everything they need to do creates cognitive overload. Instead, Mango shows only tasks that are actually ready to be worked on, helping teams stay focused and productive.

When projects reach completion, the system automatically releases associated time for billing, connecting project milestones directly to revenue. Project notes “live with this project as it rolls forward,” ensuring that when different staff members handle recurring work next year, they have access to context from previous engagements.

The capacity planning feature shows utilization across all projects and allows managers to easily reassign tasks to different team members if somebody is out or leaves the company. Calendar integration with Microsoft Outlook and Google Calendar displays all past, present, and future appointments for any team member who had appointments with that client directly within the client view.

Pricing and Technical Details

Mango offers three pricing tiers. The basic tier includes core features, while the Plus tier adds project management and budgeting. The Pro tier, at $69 per user per month, includes all features plus document management, e-signatures, and capacity planning.

For electronic payments, ACH transactions cost 1% with a $12 cap, while credit cards run approximately 3%. The platform includes a mobile app that allows users to enter time and expenses, look up client contacts, and add notes while away from the office.

One practical feature Sines highlights: if users accidentally close their browser or log out while timers are running, their timers will still be there when they log back in. “You will not lose your timers.”

The system also supports multiple browser instances, allowing users to have “project management tab open” alongside “time tracking” and “billing worksheets” on different screens while maintaining data consistency across all views.

Integration as a Competitive Advantage

Sines’ demonstration reveals why unified platforms are essential for accounting firms. The ability to handle multiple functions in one system eliminates the data re-entry, system switching, and workflow friction that drain efficiency from traditional setups.

The platform includes a master template library that anybody using Mango can access and customize. This allows firms to adopt proven processes quickly rather than building workflows from scratch.

The notification system provides what Sines calls workflow intelligence, sending alerts when specific conditions are met, such as assigning tasks, resolving dependencies, or approaching project deadlines.

For firms evaluating practice management solutions, Sines recommends visiting the Mango website to schedule a demo or attend one of their weekly webinars. “We have two webinars every single week,” he notes, where potential users can ask questions and see the platform in action.

The Move Toward Unified Systems

Firms are moving away from juggling multiple disconnected systems toward unified platforms that treat practice management as an integrated workflow.

The demonstration shows how this integration eliminates friction between core business processes. When time tracking connects directly to invoicing, when project management triggers automated billing, and when client communications embed payment options, the entire operation becomes more efficient and responsive.

As practices grow more complex and client expectations increase, the competitive advantage belongs to firms that operate as unified organizations rather than collections of separate systems. The traditional approach of patching together different solutions for each function isn’t just inefficient; it creates operational bottlenecks that can’t keep pace with modern client demands.

Watch the full demonstration to see how Mango’s unified approach eliminates the inefficiencies that come from managing disconnected systems, and discover why accounting firms are choosing integrated platforms over fragmented tool approaches.

From Burned Out to Built Up: How Workflow Systems Transform Average Accountants into A-Players

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“This is the first year where we didn’t have any crazy day during tax season,” a firm owner told Mary Delaney after 25 years in practice. The secret? They had finally mastered workflow automation, transforming their firm from a chaotic fire-fighting operation into a well-oiled machine where even tax season runs smoothly.

In this episode of the Earmark Podcast, recorded live at the Advisory Amplified conference in Chicago, host Blake Oliver sits down with two workflow transformation experts: Mary Delaney, CEO of Karbon, and Kenji Kuramoto, co-founder of Acuity and a pioneer in remote operations and client accounting services.

The trio discussed how accounting firms can break free from the exhausting cycle of individual heroics and constant firefighting. Forward-thinking practitioners realize documented workflows are the foundation for scaling beyond founder dependence and actually delivering the advisory services clients need.

From Chaos to Control: The Science of Accounting

The accounting profession has long operated as a craft, where success depended on individual practitioners juggling multiple responsibilities. But as Delaney explains, the real revolution comes from “turning it into a science” through systematic documentation and automation.

Oliver knows the old way’s exhausting reality firsthand. “In order to be an A player, you had to be really good at putting out fires, juggling a bunch of things,” he reflects. “You had to be so organized yourself. There was no support system underneath you.” He admits candidly, “I wasn’t an A player. That’s the thing. That’s why I didn’t last.”

Workflows change this equation. Instead of requiring heroic individual effort, firms create systems that support everyone on the team. Delaney’s approach starts with observation, or what she calls “time studies.”

“I’ll take a team of two or three people to our customer’s location and do an on-site for a day, literally sitting and watching our customers work,” she explains. “I’ll watch three people do their tax work for 20 minutes, or three people do advisory. You’ll see they pull up a report. You’ll see they write something down. Why are you writing that down? What are you doing with that?”

These observations reveal areas of waste, automation possibilities, training gaps, and process inconsistencies that might otherwise stay hidden.

From Struggling CFO to Workflow Champion

Kuramoto’s experience demonstrates how workflow can transform careers. Coming from Big Four audit, he founded Acuity but admits he wasn’t naturally gifted at the work. “I was a moderately technical CFO and accountant,” he says with characteristic humor. “Luckily, I have a little bit of a quirky personality and I’m pretty outgoing, so clients liked me. But I was not the most technical.”

His firm’s workflow evolution started with simply moving from paper to Excel spreadsheets. They progressed to digital task management tools, with Kuramoto initially dreaming that someday systems might automatically check off completed tasks.

“I thought for a long time that the epitome of what an ideal workflow would look like would be when you completed some task, somehow the tool just knew it and it checked it off,” he recalls. Today’s reality exceeds even that vision. “Now the workflow tool is actually doing the work. I don’t think I ever even imagined it taking that leap forward.”

Kuramoto found that workflow helped him overcome his limitations. When senior CFOs in his firm documented their processes, he learned from them quickly. “Can I please take a look at your process for how you run a board meeting or raise capital, or how you build a proforma model?” he would ask. “I could learn so much quicker by just looking at a playbook for how they got there.”

This knowledge-sharing transformed Acuity’s recruiting. They began targeting controllers and VPs of finance who aspired to become CFOs. 

Making Workflow Empowering, Not Controlling

The biggest obstacle to workflow implementation isn’t technology; it’s people. Senior professionals, especially in advisory roles, often resist standardization. Kuramoto learned this firsthand when implementing workflows with senior CFOs at Acuity.

“They are sometimes the least receptive to change,” Kuramoto admits. Despite being the founder, when he suggested creating standardized processes, the reception was cool. “To them, initially, it felt like more of an accountability tool. Like I was telling them how to work versus letting them feel like they had ownership of the work.”

Delaney’s solution centers on showing the “what’s in it for me” factor. “If we map it out, we can automate some of it. And the part we automate is the energy-draining low value work,” she explains. “All of a sudden they get to do more of what they love.”

The transformation happens when workflow becomes a knowledge-sharing tool rather than a constraint. With better visibility into how people work, firms can identify real problems. “We could identify where someone was a B or C player, but it started understanding why,” Kuramoto explains. “Were we missing out on training? Were we overwhelming their schedule? Were they stuck on tough clients?”

Delaney emphasizes that workflow reveals patterns. “You can see some people are rock stars, but instead of saying they’re just incredible, you start to study what they do and you can train that to others. All of a sudden you’re lifting your C players to be in your B to A players.”

The 30-Day Transformation Plan

Delaney offers a rapid transformation plan for firms drowning in chaos. If dropped into a small firm as CEO with 30 days to free up capacity, here’s what she’d do:

First, “I would make sure I understood what their job is, how we measure performance, and how they will be compensated and recognized.” This clarity alone can unlock 20-30% more capacity because “if people understand clearly their job and expectations and they have something they’re chasing, you will get 20, 30% more out of them.”

Second, “Look at our customers and see if there’s any we should let go or just increase the price.”

Third, conduct time studies. “Sitting there and watching people work, you can see all the areas of waste. What can we automate? You also see where there are training gaps.”

The results can be dramatic. Remember that firm with their first stress-free tax season in 25 years? “They have the process down, they have capacity planning down, they work ahead,” Delaney explains. “They have all the insights to manage every minute wisely. So it’s not putting out fires.”

Workflow as the Foundation for Growth

This workflow discipline is critical during mergers and acquisitions. Kuramoto’s first acquisition taught him this lesson painfully. “The first firm we acquired was kind of a disaster,” he admits. “We had incredibly dissimilar ways of working. Even though on paper we delivered some of the same services, the way we did it was so different.”

They waited too long to integrate workflows. “We didn’t want to disrupt things, so we waited a long time. It was an awful transaction for us, largely because we didn’t get workflow on the same page.”

This experience changed how Acuity approached their eventual merger with 14 firms. “When we went through due diligence, they looked heavily at our workflow. What were we doing? How are we putting it together? Most acquisitions don’t fail because the deal isn’t good. It’s because the integration doesn’t work.”

For firms ready to transform, Delaney emphasizes investing in dedicated operations resources. “The one thing they never regretted was hiring a non-billable person to start really moving on quality and scaling and operations,” she notes, recommending this when firms reach 10-20 people. “The gift you give yourself is having someone who spends 100% of their time looking at how to make the firm better, versus how to bill dollars today.”

The AI-Powered Future

Looking ahead, AI promises to accelerate this workflow revolution. The Karbon-Aider acquisition, announced that very morning, exemplifies this vision. “Aider is all about automating month end and getting you to insights that you can immediately share back with your customers,” Delaney explains.

But she cautions that AI requires careful implementation. “The challenge with AI is it’s highly imperfect. We’re building agents to do the work, but you have to show all the agent’s work, and give it a step for a human to check it and sign off. Because in accounting, you have to be perfect.”

The future Kuramoto envisioned is becoming reality in ways he never imagined. What started as digitized checklists has evolved into tools that actually perform the work itself.

Your Firm’s Revolution Starts Now

The conversation between Oliver, Delaney, and Kuramoto at Advisory Amplified shows the firms thriving today aren’t necessarily those with the most talented individuals. They’re the ones who’ve systematically documented and optimized how work gets done.

This transformation is about democratizing expertise across teams, creating sustainable careers that don’t require heroic effort, and delivering consistent advisory services that clients need. The stakes keep rising as AI tools mature. Firms with strong workflow foundations will leverage these technologies effectively while others risk being left behind.

The good news? You don’t need years to see results. Delaney’s 30-day plan shows that simple steps can unlock 20-30% more capacity almost immediately. And unlike the old model where success required exceptional individual talent, the workflow revolution means firms can build operations that elevate everyone.

Want to learn more about transforming your firm from chaos to capacity? Listen to the full conversation with Delaney and Kuramoto on the Earmark Podcast, where they share additional insights, implementation strategies, and discuss how AI is reshaping accounting practice. The revolution isn’t coming; it’s already here.

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.