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Blake Oliver

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.

From Vanishing Jobs to Work Slop: Inside Accounting’s AI Reality Check

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The accounting profession faces a stark reality-check as entry-level auditor positions have declined by 43% since January, and a third of accountants admit they cannot identify AI-generated fake receipts. 

In episode 455 of The Accounting Podcast, hosts Blake Oliver and David Leary address the growing evidence that AI is disrupting accounting more rapidly than most firms can keep up with. From vanishing entry-level jobs to the rise of “work slop” (low-quality AI output that wastes time and money), the profession is struggling with changes that are both promising and perilous.

The Tech Stack Problem Nobody Wants to Talk About

Before diving into AI’s disruption, Oliver shared a surprising statistic: only 37% of accounting firms require their clients to use their technology stack. That means 63% let clients choose their own tools, creating a mess of incompatible systems and inefficient workflows.

“It’s one of the things we did in my firm that was a differentiator and allowed us to scale quickly,” Oliver explained. “It reduced training time. It increased the speed at which we worked.”

The reluctance to standardize reveals a deeper problem in the profession: firms are so afraid of losing clients that they sacrifice efficiency and scalability. Yet Oliver found the opposite: “The ones that were willing to make that shift ended up listening to us about other things, too. So you might want to consider requiring clients to switch as, like a testing mechanism to see if they’re actually going to be a good fit.”

This standardization challenge becomes even more critical as firms try to implement AI. Without consistent data inputs and workflows, automation becomes nearly impossible.

The Vanishing Entry Level: A 43% Wake-Up Call

The most alarming news Oliver shared was the 43% drop in entry-level auditor job postings since January, based on a study of 126 million job postings. Meanwhile, senior positions requiring ten or more years of experience increased by 6%.

“These firms are extremely shortsighted,” Oliver argued. “They are just trying to juice profits and revenue in the short term. And the easiest way to do that is to replace your entry-level people with AI.”

The vulnerability of these positions is clear. As Oliver explained, “The stuff an entry level auditor does is so basic, like cash confirmations. You can have an AI agent doing cash confirmations all day long. It’s not complicated.”

The fear extends beyond auditing. Nearly half (45%) of accounts payable professionals now fear layoffs in 2025, up from 27% last year. These workers see AI agents matching invoices, approving bills, and processing expense reports—tasks that once required human oversight.

Leary raised an important question: Are firms actually succeeding with AI, or are they cutting staff first and hoping to automate later? In Oliver’s view, the automation is working well enough to justify the cuts. But this creates a long-term problem. Without entry-level positions to train tomorrow’s senior accountants, where will future leaders come from?

Work Slop: The $200 Hidden Cost of Bad AI

A new Harvard Business Review study coined a term for low-quality AI output: “work slop.” And work slop is expensive. Each incident wastes nearly two hours and costs about $186 per worker per month.

Forty percent of workers report receiving work slop in the past month. More than half feel annoyed when they get it, and 42% view the senders as less trustworthy.

“Every time one coworker gives another coworker slop, it costs your company 200 bucks,” Leary emphasized. But, “Employees who turn out work slop probably already did work slop before. They just did it at a much slower volume.”

The hosts shared their own experiences with work slop. Job applicants submit unedited ChatGPT responses. Guest pitches reference the wrong podcast. Some candidates even feed interview questions into AI during live video calls.

“It looks good,” Oliver said about typical work slop. “Like if you look at the email, it’s nicely formatted and it looks good and then you actually read it and you realize that it’s garbage.”

The paradox is striking: 97% of firms admit they’re not using technology efficiently, yet 86% believe AI-using firms have a competitive advantage. The gap between aspiration and execution means firms produce more low-quality work faster rather than better work more efficiently.

The Fraud Detection Crisis

Perhaps most concerning is accountants’ declining ability to spot fraud. Thirty-two percent admit they can’t recognize AI-generated fake receipts. Another 30% are seeing more fraudulent receipts than last year, and 42% suspect colleagues have submitted fake or altered receipts.

“If you want to see just how difficult it is or how easy it is to make one, just go and ask ChatGPT to make you a receipt,” Oliver challenged listeners.

Leary noted that expense fraud isn’t new. After all, people used to pick a receipt up off the ground at McDonald’s. But AI changed the game. Now anyone can generate perfect forgeries on demand.

Oliver explained that current AI models don’t understand physics, so shadows and lighting in fake images often don’t match reality. But detecting these requires expertise most accountants don’t have.

“When nothing is physical anymore, how do you, as an auditor or an accountant, rely on a scanned document?” Oliver asked, highlighting a fundamental challenge for the profession.

Solutions Emerging from the Chaos

Despite the challenges, practical solutions are emerging. Zapier announced a “human in the loop” feature that pauses automated workflows for human review at critical points. “Don’t try to automate the whole workflow,” Oliver advised. “Try to automate one task in the workflow.”

Keeper launched a new AI product that converts payroll reports and settlement statements into journal entries—a task that previously required complex spreadsheets and manual work. At $50 per client per month, it represents the kind of targeted automation that actually works.

Even Drake Software, long criticized for being behind the times, launched cloud-based tax software. While limited to certain forms, it signals that even legacy providers recognize the need to modernize.

These tools show that successful AI implementation isn’t replacing humans entirely. Instead, it augments specific tasks while maintaining human oversight for quality and judgment.

Looking Ahead: A Profession at a Crossroads

The accounting profession faces interconnected challenges that require more than technological solutions. The 43% drop in entry-level positions poses a threat to the talent pipeline. Work slop erodes trust and efficiency. Fraud detection capabilities are falling behind those of fraudsters.

Yet there are opportunities within these challenges. Firms that thoughtfully integrate AI, maintain human oversight, and invest in training the next generation will have an advantage over those who chase short-term profits by cutting entry-level positions and blindly implementing AI.

As Oliver noted about his own firm’s success, standardizing technology, requiring client buy-in, and focusing on quality over quantity created real competitive advantages. The same principles apply to AI adoption. Success requires strategy, not just software.

To hear Oliver and Leary’s complete analysis of these shifts in accounting, including their discussion of H-1B visa changes, Trump’s latest tariff threats, and more practical insights for navigating AI’s impact, listen to the full episode of The Accounting Podcast. Their unfiltered weekly discussions provide essential perspective for anyone trying to understand where the profession is heading and how to thrive despite the uncertainty.

Stop Pricing the Deliverable and Start Pricing the Relationship

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Marie Greene once spent more than 20 hours on a client she was charging just $12. But she only realized how little she was charging for her time when her firm started tracking time. While extreme, Greene’s story highlights a problem that plagues accounting firms everywhere: chronic underpricing that leaves practitioners exhausted and struggling to grow.

In this episode of the Earmark Podcast, recorded live in Los Angeles during the Advisory Amplified tour, host Blake Oliver explores the pricing puzzle with Greene, a CPA and founder and CEO of Connected Accounting, and Ryan Embree, Director of Partnerships at Ignition. Together, they tackle one of the profession’s toughest challenges: how to charge what you’re worth without losing clients.

The Time-Tracking Wake-Up Call

Greene’s journey to better pricing started with tears of frustration. “I literally cried, but I didn’t know it was so bad. My pricing was so bad until we started tracking time,” she admits. Even though Connected Accounting had always used fixed fees instead of hourly billing, they had no real grasp on whether their pricing made sense.

The problem got worse when Greene hired her first team member. She’d been pricing based on how quickly she could complete tasks, not realizing she was “super mega efficient” compared to most people. “When it takes someone a normal amount of time, I was destroying my budgets and I couldn’t delegate fast enough. And then I was just buried in work,” she explains.

This pattern isn’t unique to Greene’s firm. Embree sees it repeated across hundreds of firms he works with at Ignition. The problem often hides in compliance services, where firms fall into the trap of charging “the same as last year.”

“If you quoted someone X amount of dollars seven years ago and they’re still paying that fee, that is the biggest opportunity,” Embree points out. Many firms hesitated to raise prices during COVID when clients were struggling. But as Embree notes, “price increases are normal. They’re a part of business.”

Eventually, Greene’s managers staged an intervention. They took over pricing and told her to stop selling certain services at unsustainable rates. Six years later, the firm has a much more realistic pricing model. But it all started with that uncomfortable first step of tracking where time actually goes.

Pricing the Whole Relationship, Not Just the Deliverable

The real breakthrough came when Greene realized she was charging two clients the same amount for identical services, but one required far more time and attention than the other.

“You can’t just price the deliverable, which is a P&L at the end of each month,” Greene discovered. “You have to also price the number of touchpoints. You have to price how often they have ad hoc random questions that are not part of the scope.”

Connected Accounting now looks at multiple factors when setting prices:

  • Number of bank accounts (17 credit cards vs. one checking account makes a difference)
  • Transaction volume (one account with 1,000 transactions can be more work than multiple quiet accounts)
  • Number of bills and invoices processed monthly
  • Meeting frequency (weekly touchpoints vs. monthly check-ins)
  • Communication style and expectations

This approach also creates natural price escalators. “We’ve always been very clear up front that we grow with you,” Greene explains. “As you add employees, as you add bank accounts, as your transaction volume increases, our fees increase.”

Embree adds that this reframing helps clients understand price changes. “They know they’re growing. They know they’ve exceeded scope. So they know they’re just kind of leveling up to a new level of service.”

Beyond pricing existing services correctly, firms often miss revenue by not telling clients about everything they offer. Greene discovered this after creating a comprehensive list of which clients used which services. “I was like, oh, we only have six accrual clients, or we only have three that use X.”

This led to casual conversations during client meetings. “We’d say, hey, by the way, we notice you do this. Who does your payroll?” Greene recalls. “We’re not saying we sell payroll and you should buy it, but it was just planting a seed.” Often, clients would respond enthusiastically, not even knowing Connected Accounting offered that service.

Having the Conversation: A Live Repricing Role-Play

During the discussion, Greene demonstrated her approach to repricing conversations in a role-play with Embree acting as the client. She showed how her strategy turns a potentially awkward discussion into a collaborative planning session.

Greene starts with enthusiasm, not numbers: “Hey, Ryan, how excited are you about next year? What are you looking forward to doing with the business?”

When Embree shares his growth plans, she follows with genuine concern: “And with the growth, what are some of the things that keep you up at night?”

Only after understanding his challenges does she pivot to solutions: “Would you be interested if we can find a way to help you lower some of your costs by not having to hire one more admin, and we can take on some of the grunt work?”

The conversation naturally flows into discussing additional services like benefits renewal and talent retention strategies—services Embree’s character didn’t even know Connected Accounting offered.

After these discovery conversations, Greene presents three-tier proposals. “I was no longer trying to force a single price. I showed three and then they could choose. And that was the relief,” she explains. This approach gives clients control while removing the pressure of “selling” a single option.

Despite common fears, clients rarely leave over price increases. Embree observes, “A lot of firms that want to cut clients think raising fees is the way to go. And the short answer is no, they actually still stick around.”

In fact, the worst clients often prove surprisingly price-insensitive. “Whatever the fee is, you can’t actually price them out,” Embree notes.

Technology makes these conversations easier. Connected Accounting now automates annual increases using opt-out language in engagement letters. “Every year in December, we send a notice saying, hey, you have 30 days to cancel your services. But just so you know, effective January 1, all pricing across the firm is going up 3%,” Greene explains.

This mirrors how services like Amazon Prime handle increases: making them expected rather than exceptional. As Oliver points out, “That fee just goes up every year. And we get the email and we look at it and we accept it.”

Your Pricing Transformation Starts Now

Greene’s journey from charging $12 for 20-plus hours of work to running a profitable firm with systematic pricing shows that transformation is possible, even if it takes time. The lessons are: track your time to understand true costs, price the entire client relationship rather than just deliverables, and reframe price discussions around growth and value.

The fear of losing clients to price increases is largely unfounded. When one client left Connected Accounting for a competitor offering a deal, they returned after 12 months and started paying the competitor’s higher rate, which Greene then maintained. “The market often values accounting expertise far more than practitioners themselves realize,” she discovered.

Greene admits she still gets nervous before pricing calls. But she’s learned that authenticity matters more than perfection. “They see how excited I get. They know I’m a huge nerd, I love technology, I love accounting,” she says. “Eventually, they’re like, okay, cool. She sounds like fun to work with.”

Embree emphasizes that positioning yourself as an expert dramatically increases what clients will pay. “People’s willingness to pay is infinite for that piece of mind,” he notes. “To know that you have an expert in your corner that has done this with other clients and knows everything about you and your business.”

The profession’s chronic underpricing doesn’t just hurt firm owners; it limits the entire industry’s ability to innovate and serve clients well. When accounting professionals charge appropriately, they can invest in better tools, training, and talent.

Ready to stop leaving money on the table? Start by tracking where your time really goes. Then look at your client list and identify who’s grown beyond their current service tier. Finally, practice having value-focused conversations that celebrate client success rather than apologizing for price increases.

The full episode includes the complete repricing role-play, detailed pricing metrics, and specific strategies you can implement this week. Because as Greene’s story proves, the biggest barrier to profitable pricing isn’t your clients’ willingness to pay. It’s your own reluctance to ask.