Megan Reid

The Month-End Close Is Accounting’s Biggest Bottleneck. Here’s How AI Is Dismantling It

Earmark Team · May 7, 2026 ·

The day before a tax deadline, and accountants from Miami to Vancouver, Portland to New York, logged into a CPE-eligible webinar to learn something that could fundamentally change how they work. The webinar showed how these professionals can shrink the most time-consuming part of their month-end close, like reconciliations, transaction coding, and bank statement chasing, from days to minutes.

Megan Reid, product specialist at Digits, led the session, and she brings a unique perspective. She’s an accountant with 15 years in the trenches, starting at a Big Four firm, moving through banking and construction, and now helping firms build what she calls an “AI-native” practice. As she put it to the audience, “As accountants, we want to be able to serve more clients, provide better service, and do so quickly and efficiently.”

The traditional month-end close is accounting’s biggest bottleneck. It’s that manual grind through booking transactions, reconciling statements, updating schedules, reviewing anomalies, and (if there’s time left) analyzing the numbers and creating the reports clients care about. “It’s a manual, tedious, time-consuming process that honestly leaves a lot to be desired for both the business owners and the accountants,” Megan said bluntly.

But what if you could flip that entire workflow? What if instead of reviewing every transaction, you only touched the ones AI couldn’t confidently handle? That’s exactly what Megan demonstrated live, showing how AI-native platforms transform the close from a compliance chore into an opportunity for real advisory work.

The bottlenecks killing your efficiency

Before diving into solutions, Megan mapped out where the traditional close breaks down. You start in QuickBooks or your ledger of choice, but quickly find yourself bouncing between Excel, browser tabs for vendor research, your close management tool, and who knows what else. “Not only are you managing the work across all these multiple platforms,” she explained, “you’re also spending time validating sync accuracy, troubleshooting issues, and making sure the data moves seamlessly throughout the various systems.”

Each phase has its own special frustrations:

Manual data entry and rule management introduce human error
Fighting with bank access and chasing clients for statements
Disconnected tools for AP, credit cards, and close management
Team members use different processes, causing rework and confusion
Manual journal entries pile up at period-end

As a result, most of your time goes to necessary but low-value tasks, leaving little room for the analysis and insights your clients actually hired you to provide.

How AI learns your way of doing things

The shift to AI-native platforms involves intelligence that learns and adapts. When Megan pulled up the demo client in Digits, she showed hundreds of transactions the AI automatically categorized. Only eight were flagged for review.

“How does it know how to categorize transactions?” she asked, anticipating the obvious question. The answer lies in three layers of learning.

First, there’s client-level learning. When you correct a categorization for a specific client, the system learns instantly. “If you review something for a brand new client and you say, ‘nope, you categorized this to software, but I actually want it to be cost of revenue,’ Digits learns from that instantly,” Megan explained.

Second, there’s firm-level learning. The system recognizes patterns across your entire client base. If the system does not have the client-level layer of knowledge, it falls to the firm-level. “How has my firm done this across all of my clients? It automatically applies your firm’s unique value to your client base.”

Third, when a transaction is entirely new, proprietary models trained on billions of dollars’ worth of transactions make the call.

During the live demo, Megan reviewed a U.S. Patent and Trademark Office transaction the AI thought might be taxes. She looked at the suggestions (taxes, legal, or a new intangibles account), selected “Legal,” and clicked save. The system immediately found two similar transactions and updated them automatically. The review queue dropped from eight to five in seconds.

But what really eliminates busywork is the AI agents run 24/7 in the background, researching vendors and populating details. “None of this has been populated manually,” Megan showed, clicking through a vendor profile complete with name, logo, description, and related websites. “We’re essentially researching them and populating all of the data for you.”

Bank reconciliation without the chase

If transaction categorization is tedious, reconciliation might be even worse. You know the drill: fighting for bank access, emailing clients for statements, then manually comparing the ledger to the statement line by line.

Megan demonstrated the “happy path” first. Digits pulled a Mercury bank statement via an API, automatically kicked off reconciliation, matched every transaction with pixel-level precision on the PDF, confirmed the ending balance, and finalized everything. Zero human touches required.

“Some firms we work with actually say, ‘I uploaded six months of bank statements and just watched them finalize one by one. And I didn’t do anything,'” Megan shared.

When auto-reconciliation can’t finalize completely, it doesn’t leave you guessing. The system flags specific issues, such as:

Missing transactions that exist on the statement but not in the ledger (one click to create)
Date mismatches where something cleared May 31 but hit the ledger June 1 (one click to adjust)
Unsettled items like checks that haven’t cleared yet

For banks without API access, such as small credit unions, you simply drag and drop a PDF statement. During the demo, Megan dragged a statement into the system and watched it extract data and start reconciling in seconds.

She took it further with a cleanup scenario. Starting with a brand-new bank account, she imported a PDF statement. Within moments, 14 transactions appeared as uncategorized. Seconds later, the AI had populated every vendor name and category without a single manual input.

Turning saved time into client value

Speed alone isn’t the point. As Megan emphasized, “the compliance and the month-end close is really just a means to an end,” the end being insights and value for clients.

The dashboards in Digits default to the current month because, as Megan noted, “knowing something two months late doesn’t usually help.” Every metric is live and drillable. Click into gross income, and you see the definition, calculation, and every underlying transaction. Your clients finally understand how you arrived at the numbers.

Each client gets customized dashboards. “Maybe you have a client that’s like, ‘we’re spending so much money on travel,'” Megan explained, showing how to add customized metrics that are specific to each client. A profitable client with ten years of runway might swap that widget for gross profit or vendor analysis.

Collaboration happens right on the platform. On any transaction, category, or report, you can leave a question. The client receives a notification and can respond directly from email without logging in. “One of the biggest pain points is transfer of knowledge,” Megan said, “making sure that you have everything that you need from your clients and vice versa.”

Custom reports become interactive stories rather than black-and-white PDFs. The AI generates insights like “You earned 33% more in March compared to the prior month” with drill-down capability to see exactly why. Important insights can be pinned to the executive summary so they’re the first thing clients see.

What this means for your firm

During the Q&A, attendees asked practical questions. One wondered if this integrates with QuickBooks or replaces it entirely. “Digits is a complete ledger system. So it’s a complete replacement,” Megan answered. They can migrate QuickBooks data in about two minutes, but this is a ground-up rebuild, not a bolt-on tool.

Another attendee asked about company scale. The focus is on small and medium-sized businesses, which is the client base most firms serve.

The shift from reviewing everything to reviewing only exceptions makes the close faster and more consistent across your team, less error-prone, and it frees up capacity to serve more clients without hiring proportionally.

“It’s a very exciting time to be an accountant while also a little bit scary,” Megan acknowledged near the session’s end. “I think it’s a time to really lean in and be excited.”

She’s right. The firms embracing AI-native tools now will deliver premium advisory services while their competitors are reconciling bank statements at midnight.

To see these workflows in action, watch the full webinar. Every accountant who signs up gets access to a sandbox demo environment where you can test these workflows with real data. And if you attended live or watch the recording, you can earn CPE credit through the Earmark app. Just search for the course and complete the quiz.

The close is changing. Will you lead that change or follow it?

Not All AI Is Created Equal and Your Next Software Decision Depends on Knowing the Difference

Earmark Team · April 17, 2026 ·

When Jeff Seibert ran consumer product at Twitter, he asked the finance team for his budget to throw a team event. They said they’d get back to him in 45 days. So he just ran the event without them.

That gap between real-time data and 30-to-90-day delayed financial reports was frustrating, and it eventually led Jeff to build Digits, a new general ledger designed from scratch for the machine learning age. After raising $100 million pre-launch, testing 2,000 monthly closes, and getting 80% of clients closed in under an hour, Digits launched in March 2025. Now, just over a year later, hundreds of accounting firms are onboarding thousands of clients onto the platform.

Jeff launched Twitter’s algorithmic timeline in 2016, and it was one of the first global deployments of machine learning. Now, the AI revolution Jeff helped launch is flooding the accounting profession with claims that are hard to verify. Every accounting software company seems to include AI in its marketing copy, promising everything from “fully automated bookkeeping” to capabilities that don’t add up under scrutiny.

In a recent Earmark webinar, host Blake Oliver and Rob Hamilton, Head of GTM at Digits, pulled back the curtain on how AI in accounting actually works. He was joined by Megan Reid, Product Specialist & Firm Enablement at Digits, who fielded questions throughout the session.

Every AI claim in accounting software isn’t real. But accountants who understand the four core model types (plus one common lie) will make smarter investments, automate the right parts of their workflow, and position their firms for a shift Rob sees coming by the end of 2026.

The AI hype problem (and one question to cut through it)

Before making any technology decision, you need a filter for separating real capabilities from marketing fluff. Rob offered a simple one that cuts through the noise.

He showed screenshots from multiple accounting software companies making bold AI claims. One promised “fully automated bookkeeping.” Another asked, “Do you do AI bookkeeping or do you use a dedicated team of experts?” The positioning has gotten so confusing that firms can’t tell what’s real anymore.

The confusion isn’t new. About five years ago, tech investor Naval Ravikant tweeted, “In most pitch decks, AI stands for Anonymous Indians.” For a long time, that was literally true. Services like Botkeeper rose and fell using offshore labor dressed up as automation. Today, “AI actually means we just bolted on and sent all of your data to ChatGPT,” Rob explained.

Here’s your filter: “AI is the same thing as machine learning,” Rob stated. “If someone is talking to you about AI and they’re not referring to machine learning as the underlying premise, it’s just BS.”

But this filter only works if you understand what machine learning actually is.

Traditional software is straightforward. You write code that tells the computer exactly what to do. It’s tedious to build, but rock solid once it works. Machine learning flips this completely. You feed the system thousands or millions of examples, and the model learns the patterns itself. As Jeff explained in a clip Rob played, “You give the computer the goal state—I want this outcome—and then the computer itself is learning how to do it.”

These models are neural networks. Thousands of hidden layers mimic how neurons connect, based on Google’s 2017 “transformer” research paper (the “T” in GPT). It’s a massive matrix multiplication problem where the system figures out how variables relate to each other.

But machine learning isn’t one thing. Different model types have different strengths and uses in accounting. Understanding these distinctions helps you avoid buying the wrong software and shows you exactly where AI can save time and where vendors are overselling.

The model types that matter (and one that doesn’t)

Rob walked through five categories that get lumped under “AI,” but understanding the differences is what separates informed decisions from expensive mistakes.

Generative models

Large language models (LLMs) are the ones you hear about most, ChatGPT being the prime example. GPT stands for “Generative Pre-Trained Transformer,” and these models generate the most likely continuation of whatever prompt you give them. Rob showed a useful application: turning bullet-point close notes into polished client emails. His advice is to write a “job description” for the AI once. Tell it who it is, give context, specify output format, add examples. Then just paste in different client notes as needed.

But generative models have serious limits. They’re “super eager” and always want to complete prompts, making them prone to hallucinations, or making things up that sound real. They’re bad at math because they generate text rather than calculate numbers. And they’re trained on the internet, not your specific clients. “The ways that it is hallucinating is stuff that maybe even is hard for humans to catch sometimes,” Rob warned. Always review the output.

Agents

These are LLMs with help. You give them a job description, a task, and tools, like computer programs they can use to generate reports, list accounts, or run calculations. The agent makes a plan, uses its tools, checks if the task is done, and loops until complete. Rob showed Digits’ agent answering “I want to hire 20 software engineers next year. Can I afford to?” with a data-backed response.

Guardrails are critical. Microsoft’s early agent “started asking people on dates in the chat,” Rob noted. “You don’t want your accounting agent dispensing dating advice.” Agents work well for updating schedules, running quality checks, and answering analytical questions, but they’re slow and need careful boundaries.

Predictive models

These got Rob visibly excited, and for good reason. These models take an input and predict an output from known options. When the model sees a $5 Starbucks charge, it considers the client’s location, history, and chart of accounts. For a local client, it’s meals and entertainment. For a New York client in California, it’s travel. A $157 Starbucks charge is probably an event, regardless.

What makes predictive models perfect for transaction categorization is they can’t hallucinate; they only choose from existing options. They’re deterministic (same input, same output), include confidence scores, and run fast and cheap once trained.

Digits built a “layer cake” of predictive models:

Client-level (learns each business)
Firm-level (encodes your best practices)
Global (trained on 180 million transactions worth nearly $1 trillion)
An LLM fallback for completely new transactions

The result was over 97% accuracy, compared to standalone LLMs that plateau below 80%, which is about the same as outsourced bookkeepers.

Document extraction models

These combine OCR with layout-aware language models that understand document structure. Previous tools used Amazon’s Mechanical Turk, which relied on humans manually extracting data and took hours. Modern extraction models work in seconds. Digits’ bank reconciliation automatically pulls PDF statements, matches transactions to the exact spot in the PDF, and generates audit reports.

Data analysis

This model is where Rob pulled the rug out. Financial reporting and analysis is “actually just math. It’s not ML.” Computers have done statistical analysis for decades. Could you build an agent to do it? Sure, but it would be slow, expensive, and probably wrong. “If anyone says their AI does reporting and statistical analysis, please ask them what they’re talking about.”

Here’s how the right models map to your month-end close:

Book transactions: Predictive models (with LLM fallback)
Reconcile statements: Extraction models plus matching algorithms
Update schedules: Agents
Review and correct: Agents with quality checklists
Analyze and report: Statistical analysis plus agents for questions

“Shoehorning an LLM in to solve a problem and just sending a bunch of information is fundamentally incorrect,” Rob emphasized. Each step needs the right model. No single AI approach handles everything.

The 2026 prediction

Understanding model types is just the foundation. The urgency comes from how fast everything is converging.

“Across a large client set in different industry types, it’s highly likely that the month-end close process is looking to be completely automated by the end of 2026,” Rob predicts. Even his “95% automated” hedge probably sounds aggressive. But his logic follows directly from the technology.

If predictive models hit 97% accuracy on transactions, extraction models automate reconciliation in seconds, agents handle schedules and quality control, and statistical analysis covers reporting, then manual work drops to a fraction. Rob’s goal is to see accountants doing “1/20th of the work you’re doing today.”

He acknowledged limits. Construction firms with complex job costing might not hit that threshold. But for firms serving professional services, cash-basis businesses, and straightforward accrual clients, the automation curve is steep.

An AI-native firm will focus on value instead of tedium. Deeper industry expertise. Stronger client relationships. Higher margins. You’re not reviewing every transaction, you’re supervising the system and handling exceptions. Those hours saved on reconciliation become advisory time clients actually value.

But this is also a competitive necessity. “AI won’t replace you. Someone who’s good at using AI is going to,” Rob said, quoting a common warning. And he was direct about the stakes. Firms that don’t adapt will face “a cascading effect on business models” as early adopters pull ahead.

For overwhelmed firms, which Rob acknowledged includes most firms, he offered practical starting points:

Map your processes first. If you use workflow tools like Karbon or Keeper, you’ve probably documented your steps. If not, start there. You can’t identify where AI fits until you know what you’re actually doing.
Start small and low-stakes. Don’t tackle your biggest challenge first. Try drafting emails, testing categorization, or visualizing data. Build your intuition gradually.
Get hands-on with new tools. Rob mentioned being impressed by Claude Opus, which could build HTML dashboards from his data (something he couldn’t do as a non-engineer). The specific tool doesn’t matter; hands-on experience builds judgment.
Know your business before choosing where to start. As Rob put it, “You need to know the details of your business to know where you can start and where the right places to poke and prod are.”

The “wait and see” window is closing. Firms that develop AI literacy now by asking questions about models, data handling, and use cases, will be ready for the rest of 2026 and beyond.

Your next move: Better questions, smaller steps, faster action

Let’s turn Rob and Megan’s insights into actionable takeaways:

Not all AI is equal. Four real model types plus one fake (data analysis) get lumped together. When vendors pitch “AI-powered reporting,” you now know to dig deeper.
Each close step needs a different model. Predictive for transactions. Extraction for reconciliation. Agents for schedules. Statistics for reporting. Anyone claiming one solution does everything deserves scrutiny.
Predictive models beat LLMs for categorization. Layered architectures that learn your clients and firm patterns dramatically outperform chatbots. Bigger isn’t always better.
Ask vendors the hard questions. What model type? Where does data go? Are you training your own models or sending financial data to third parties? This is due diligence.
The tipping point is closer than you think. Whether Rob’s 2026 prediction proves exactly right or directionally right, the trajectory is clear. Understanding these distinctions now positions you to take action.

For those interested in going deeper, Rob mentioned resources like the AI Native Accounting Foundation and the AI-Native Accounting podcast hosted by Kacee Johnson, where industry leaders discuss the latest developments.

The accounting profession is at a real inflection point. Smart firm leaders will develop the literacy to ask smart questions, experiment in the right places, and redirect time from tedium to advisory work clients value.

Rob noted this might be one of the few professions with such clear AI use cases, putting accountants at the forefront of innovation. That’s an opportunity to shape how technology serves the profession, not the other way around.

Watch the on-demand webinar for complete details, including live demonstrations, security architecture specifics, and audience Q&A covering nonprofits, inventory clients, and platform migrations. The future of accounting is being written now. Make sure you’re part of the conversation.