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Tax Automation

AI Agents Now Complete Tax Returns Start to Finish While the Government Can’t Even Audit Its Own Books

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The US government just declared itself insolvent. AI agents are completing tax returns without human intervention. And the accounting profession is caught between these two massive disruptions.

In Episode 481 of The Accounting Podcast, hosts Blake Oliver and David Leary opened with a bombshell that somehow flew under the mainstream media radar. The Treasury Department’s own financial statements show the US is $42 trillion in the red, and that’s before counting Social Security and Medicare obligations. They then dove into an equally seismic shift with guest Kenji Kuramoto, founder of Acuity and newly appointed Managing Partner in Residence at AI company Basis, exploring how artificial intelligence is transforming every corner of the accounting world.

Deficit Spending Just Keeps Going

“It’s official. We are insolvent,” David announced at the start of the episode, referencing the Treasury’s 2024 financial statements. They show $6 trillion in total assets against nearly $48 trillion in total liabilities. That $42 trillion hole doesn’t even include the $88 trillion in unfunded Social Security and Medicare obligations sitting off the balance sheet.

“Imagine a family making $52,000 that owes $1.3 million in a line of credit,” Blake said, putting the crisis in household terms.

Making matters worse, the Government Accountability Office issued a disclaimer of opinion for the 29th consecutive year, essentially saying it can’t even verify the accuracy of the numbers because the Department of Defense has never passed an audit.

“This is the reason a huge number of people voted for Trump,” David said. “They wanted to stop deficit spending, and it just keeps going.”

Meanwhile, AI Is Eating the Accounting Profession

While the government’s books are falling apart, AI companies are racing to automate the work of keeping everyone else’s books together. TaxGPT announced an AI agent capable of completing 1040 returns from start to finish without a preparer touching a keyboard or mouse. The tool works with existing web-based portals and tax prep software, pulling in W-2s, 1099s, and other source documents, then having a review agent double-check everything.

“Why go after tax pros?” David asked. “Just get in bed with the portal companies and go after TurboTax.”

Kenji, who recently joined Basis after selling Acuity and taking a year off, described watching AI agents handle complex accounting work that made him come out of retirement. “I saw an agent handle complex payroll entries like booking the GL entry, creating an accrual because the pay period didn’t align with month-end, posting the reversing entry for the following month, and building a complete set of work papers,” he said. “I saw this last year, and I was like, wait, what?”

The flood of AI announcements kept coming throughout the episode:

  • Ramp launched an accounting agent that auto-codes transactions down to the line-item level on invoices, claiming to save finance teams 40+ hours per month
  • Xero announced a multi-year partnership with Anthropic to integrate Claude AI directly into its platform
  • Canopy launched a bookkeeping module with AI that continuously reviews books and flags issues in real time
  • Double (formerly Keeper) released AI Journal Entries that can handle complex, repetitive entries from source documents
  • BILL announced agents for invoice coding, W-9 collection, and automated vendor payment responses

“Everyone thought we were boring,” Kenji said. “Look at this. All these Y Combinator companies spinning up and fundraising announcements and agents everywhere. Come on. Exciting.”

The Skills Gap Is Already Here

The shift is showing up in real time in hiring data. In 2023, only 18% of accounting job postings mentioned AI skills. Now it’s 30%, a 67% increase.

“The real-world requirement is probably 50%,” David argued. “People are behind on updating their postings.”

But a better question is what happens to the business model. Kenji described how at Acuity, the bottleneck was always people. Plenty of companies needed help with their books, but you couldn’t hire enough accountants to serve them cost-effectively. AI agents break that constraint. One highly efficient bookkeeper might handle 45 to 60 clients today. “Will one person eventually be able to handle 200 clients?” David asked.

The threat isn’t just from other firms. An article on Payments.com found that everyday taxpayers are already using ChatGPT and Gemini to do their taxes before ever talking to a professional. The reason is “speed and simplicity,” David explained. “AI can explain tax concepts, organize the documents, and suggest deductions. These are things they’re not getting from their tax professional.”

Are Tokens the New Billable Hour?

As AI cuts the time needed to complete work, firms are scrambling to figure out how to price their services. Bloomberg Law reported that PwC, KPMG, and RSM are all exploring alternatives to hourly billing.

“This may be the thing that finally gets us there,” Kenji said about moving away from billable hours. “If I just used AI to help me get my work done and I’m cutting down my billable hours, I’m losing revenue.”

“You can bill for tokens,” David suggested, offering a provocative alternative.

He then vented about Earmark’s own token consumption across multiple platforms, including Claude, GitHub Copilot, Retool, ChatGPT, and more. “Two days ago, an automation stopped working,” he said. “We spent five plus people hours trying to increase our tokens and get the automation working again.”

The problem is, token costs are opaque and growing. David introduced two terms gaining traction: “token anxiety,” or not knowing what you’re being charged for, and “AI FinOps,” managing AI costs across platforms.

“There’s an opportunity here for firms to become a token expert and offer it as a service,” David suggested.

Blake’s take was more pragmatic. “It’s better than timesheets, that’s for sure.”

The Window Is Closing

The government that sets the rules can’t even audit its own books while declaring itself insolvent. Meanwhile, AI agents are automating core accounting work at a pace that makes the shift from paper to computers look gradual.

“These agents are actually now becoming a component of our workforce,” Kenji said. “You’ve got accountants and you’ve got agents. This is the future state we’re moving into.”

For practitioners, it’s clear that the tools to dramatically expand your capacity exist right now. But so does the threat of clients going straight to AI and bypassing your firm entirely. The window to adapt is open, but it won’t stay that way for long.

As Blake noted about current AI pricing, “When Uber was new, everything was really, really cheap.” The subsidies won’t last forever. To thrive, firms need to figure out the new economics now, whether that’s value pricing, token billing, or something else entirely. Those that don’t may find themselves as obsolete as the government’s ability to balance its own books.

Listen to the full episode for the complete discussion, including deeper dives into specific AI capabilities and Kenji’s firsthand perspective from inside an AI-native company.

The Privacy Excuse for Not Using AI in Accounting Just Lost Its Last Leg

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Blake Oliver needed to file a City of Los Angeles business tax return for his last remaining bookkeeping client. Instead of spending 30 minutes clicking through websites and copying numbers, he gave Claude Cowork a single instruction: “Search my email for info about the account and help me file it on the city website.”

What happened next, documented on a recent episode of The Accounting Podcast, shows exactly where the accounting profession stands with AI adoption. The AI agent searched Blake’s email, found the tax notice, extracted the business details from a PDF, logged into the city website, navigated to Xero to pull gross receipts, filled out the return, and drafted the client confirmation email. Total human involvement: one correction when it pulled accrual instead of cash basis numbers.

“This is a task that might take 15 to 30 minutes if you filled out a time sheet. Claude just did it,” Blake told co-host David Leary during their weekly news roundup.

The Numbers Show AI Closing In Fast

OpenAI didn’t just release another model update with ChatGPT 5.4. It specifically targeted the kind of work that fills an accountant’s day. As David read from OpenAI’s announcement, the company “put a particular focus on improving GPT 5.4’s ability to create and edit spreadsheets, presentations, and documents.”

The benchmarks back up that focus. Using something called GDPval—which measures performance on real-world knowledge tasks across 44 occupations—ChatGPT 5.4 now beats or ties industry professionals 83% of the time. On spreadsheet tasks specifically, it jumped from 68% accuracy to 87% in a single generation.

“It’s getting close to that 90% success now on everything,” David observed. For context, that means if you give an accountant and this AI the same spreadsheet task, the AI will match or beat the human’s performance nearly nine times out of ten.

Real Accountants, Real Work, Zero Software Costs

While Blake was experimenting with Claude for business tax returns, a developer went further. Fed up with TurboTax, he used Claude to complete a 42-page federal return plus two trust returns, all at zero software cost beyond his AI subscription.

His approach was surprisingly low-tech: Downloaded blank PDFs from the IRS, have Claude fill them out, then print and mail. The biggest challenge wasn’t getting the AI to do the calculations or understand the tax code. It was trying to make it work with the IRS’s online fillable forms. So he skipped that part entirely.

“The comments were like, ‘Can I quit doing my returns tomorrow? I’ve been waiting for this my whole life,'” David said, describing the reaction from tax professionals who saw the developer’s work on social media.

The timing is notable. These experiments happened during tax season, when practitioners are supposedly too busy to explore new tools. Yet here’s a developer replacing TurboTax with Claude, and Blake casually using an AI agent for client work.

The Privacy Excuse Just Disappeared

Most firms claim they can’t use AI because client data is too sensitive. This week, Zapier offered a solution to the privacy problem.

Its new AI Guardrails can detect over 30 categories of personally identifiable information, redact sensitive data before it reaches AI systems, block workflows when it detects problems, and identify attempts to manipulate the AI. You insert it as a step in any workflow, and it sanitizes the data before AI ever sees it.

“If you have client data being passed through Zapier into any AI tool, go add this step to your workflows,” David advised listeners.

Blake was even more direct about the implications. “I totally see this being a huge tool for accounting firms, because we have all this information we want to use with AI. But a lot of it is too sensitive. That’s the main reason most firms aren’t doing anything with it.”

Beyond AI: The Week’s Other Bombshells

While AI dominated the discussion, Blake and David covered several other major stories that accounting professionals need to know about, including:

The Botkeeper Collapse Gets Messier

In an interview with Accounting Today, CEO Enrico Palmerino claimed the company went from healthy to dead in eight days. But Blake uncovered how Botkeeper engineered its financials by selling their bookkeeping clients to a firm called Benchmark Cloud Accounting. It then had that firm buy a multi-million dollar Botkeeper license. “That is how you turn service revenue into SaaS recurring revenue,” Blake explained.

Iran’s Drone Economics

The cost disparity between Iran’s drones and America’s million Interceptor missiles raises questions about the financial sustainability of current military strategies. “We’re spending $3 million to shoot down something that costs $20,000 to $50,000,” Blake pointed out.

KPMG and Polymarket

Anonymous accounts on the prediction market Polymarket have been suspiciously successful at betting on earnings for companies audited by KPMG- (and only KPMG) audited companies. The amounts are small so far, but as David noted, “Are they doing it on the real derivative markets as well?”

Record 401(k) Withdrawals

Vanguard reports hardship withdrawals have tripled since 2020, jumping from under 2% to 6% of participants. Despite positive business sentiment, individual financial stress is climbing.

What This Means for Your Firm

General-purpose AI agents can complete multi-step workflows across email, accounting systems, and government websites. The privacy barriers that kept firms on the sidelines now have concrete, deployable solutions. The capability exists. The safety tools are live. The only question is timing.

Blake’s Claude experience offers a preview of the emerging division of labor. AI handles the execution, humans provide the judgment. The AI pulled the wrong basis for the numbers. Blake caught it. That’s where professional value lives now, not in the clicking and copying, but in knowing what the AI doesn’t know to check.

The message might seem poorly timed to practitioners overwhelmed by tax season. But accountants are eager for tools that eliminate the drudgery, even in the thick of deadline pressure.

Listen to the full episode to hear Blake walk through his Claude workflow step by step, get David’s take on what ChatGPT 5.4’s benchmarks really mean, and understand why the Botkeeper story matters for anyone considering AI-powered bookkeeping solutions. The episode reflects a profession at an inflection point—not in some distant future, but this week.

The End of Data Entry and What It Means for Your Tax Practice

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Elizabeth Beastrom left public accounting 30 years ago because she was sick of rekeying data into tax returns. Now, as President of Tax and Accounting Professionals at Thomson Reuters, she works to make sure no accountant has to do that mind-numbing work ever again.

“I was a lazy CPA,” she admits with a laugh during this episode of the Earmark Podcast. “I didn’t want to spend my time doing work that I didn’t think was necessary.”

In this conversation with host Blake Oliver, Elizabeth and Kirat Sekhon, Thomson Reuters’ Head of Technology, map out their vision for automating the entire tax workflow, from gathering documents to delivering returns. They want listeners to know that AI-enabled firms are going to outcompete everyone else, and the shift from compliance to advisory isn’t optional anymore.

Why Tax Firms Can’t Keep Doing Things the Old Way

The numbers tell the story. Fewer people are taking the CPA exam while more accountants retire every year. Meanwhile, tax complexity keeps growing, which means more demand for services with fewer people to do the work. Throw in private equity firms buying up practices and pushing for efficiency, and you’ve got a perfect storm.

But it’s not just about headcount. The new generation of accountants expects modern tools that actually work together—not the clunky desktop software their predecessors put up with.

“They expect to use intuitive and connected tools,” Kirat explains, “so they have a better experience while they deliver value to their customers.”

So why has tax software stayed stuck in the desktop era while cloud accounting tools have taken off? Kirat points to two reasons. First, tax calculations are hard to get right, and once you build something that works, nobody wants to break it. Second, accountants themselves haven’t pushed for change. When you’re working 80 to 100 hours during busy season, the last thing you want is to learn new software.

“The term SALY—same as last year—still comes through,” Elizabeth notes. “You found a way to do it and you like to replicate that. Change is hard, especially when you have to introduce that to the firm when you’re working 80 to 100 hours a week.”

But resistance to change is becoming dangerous. Elizabeth’s own exit from the profession 30 years ago shows what happens when the work becomes too tedious. Back then, she discovered she loved the advisory side, including talking to clients, understanding their businesses, and making recommendations that actually helped them improve. But she was stuck doing data entry.

“I would spend time talking to my customers,” she recalls. “Some of my best inputs came from the people in accounts payable or accounts receivable. I would get a detailed understanding of their process.” But then she’d have to go back to rekeying tax data, and the contrast was too much.

Building the “Bookends” Around Tax Prep

Thomson Reuters isn’t trying to fix one piece of the tax workflow; they’re automating the whole thing. Their strategy focuses on creating what Elizabeth calls “strong bookends” around their core tax engines (GoSystem Tax, CST, and UltraTax).

The front bookend came through their acquisition of SurePrep three years ago. Practitioners dump all their client documents into the system, and SurePrep automatically classifies them, pulls out the relevant numbers, creates a binder for review, and fills in the tax software. No more manual data entry.

“That’s a huge time savings when you don’t have to spend time doing all of that manual data entry,” Kirat says, “and they can actually focus on the return.”

The back bookend arrived with SafeSend, acquired earlier this year. It handles return delivery, e-signatures, and payment collection, eliminating what Elizabeth remembers as the nightmare of printing, mailing, and faxing documents back and forth 30 years ago.

What’s different about Thomson Reuters’ approach is they’re keeping these tools open to work with competitors’ software too, not just their own tax products.

“It is an open, curated ecosystem,” Elizabeth emphasizes. “If customers find value in part of their workflow, we want to make sure we connect to it.”

Beyond just automating existing steps, they’re trying to eliminate unnecessary work entirely. Take the client questionnaire—that paper organizer Blake’s mom still fills out by hand every year. Thomson Reuters wants to “kill the questionnaire” by using AI to pre-populate information from prior returns and only ask for what’s actually new or missing.

The next frontier is what Kirat calls “agentic AI,” systems that don’t just handle one task but orchestrate entire workflows. These AI agents can use multiple Thomson Reuters products in sequence, making decisions along the way to get a return from start to finish with minimal human intervention.

But everything the AI does needs to be auditable. Kirat stresses that any AI handling tax work must show exactly what decisions it made and why.

“Our customers expect the work product of an accountant to be 100% accurate,” she explains. “Without providing that audit log with the decisions and choices and confidence levels, we’re missing the mark.”

Blake agrees enthusiastically, sharing his frustration with current AI tools that don’t show their reasoning. “I want to know why it matched this transaction,” he says. “There’s an AI conversation for each one of these transactions. Why not give that to us?”

The Shift to Advisory Can’t Wait

If machines can prepare returns faster and more accurately than humans, what exactly are clients paying for? Two-thirds of Thomson Reuters’ customers say they want to shift to advisory services, but most don’t know how to actually do it.

Enter Ready to Advise, launched in June 2024. The tool takes everything from a completed return and analyzes it against potential tax strategies based on that client’s specific situation and goals.

“It will quantify the savings,” Elizabeth explains. “It will ask for more information to get to a range. It will allow you to have that discussion where you can say, ‘Hey Blake, I noticed from your 1120-S filing some potential strategies you should take.'”

Then it walks you through implementing those strategies and produces client-ready documentation. For firms struggling to move beyond compliance, this is huge.

But technology alone won’t fix the business model problem. Clients have been trained to expect strategic advice for free. “I might call my accountant and say, ‘Hey, tell me what this big beautiful bill does for me this year?,’ which is code for don’t charge me for this,” Elizabeth says, capturing the conundrum perfectly.

That’s where Practice Forward comes in. It’s Thomson Reuters’ tool for helping firms understand their worth and develop advisory pricing models. The goal is shifting from hourly billing for returns to year-round advisory subscriptions.

Ready to Advise also solves a talent problem. Traditionally, you needed years of experience before you could offer meaningful tax advice. But with AI assistance grounded in Checkpoint’s content (maintained by over 4,500 subject matter experts), newer staff can contribute to advisory work much sooner.

“That junior associate’s experience, paired with all the knowledge that there is available in generative AI today, is incredibly powerful,” Kirat notes.

Blake shares a personal example that drives home the value of advisory over compliance. His tax preparer advised setting up a C-Corp to potentially qualify for QSBS treatment, which could save millions in taxes someday.

“I can’t even quantify the value of that,” Blake says. “But that’s why I’m willing to pay thousands of dollars for a tax return. It’s that insight, not the return.”

Meanwhile, DIY tax software keeps getting better. Blake describes doing a business return himself using consumer software with ChatGPT open for research. The same process would have taken hours of manual work just a few years ago.

Firms that stick to just preparing returns are going to get squeezed from both ends.

“AI-enabled professionals and firms, they’re going to outcompete and outperform,” Elizabeth warns, “because they’re going to be able to do it faster, better and get to this advisory, which our clients want.”

What to Do Right Now

So where should a traditional tax firm start? Elizabeth recommends figuring out what you hate doing.

“What are your pain points that you hate to do?” she asks. “There’s a pretty high likelihood that I or a talented person on my team is going to be able to say, ‘This is how we can solve that for you.’”

The technology exists today. SurePrep can handle document gathering. SafeSend can automate delivery. Ready to Advise can help you identify tax-saving opportunities. CoCounsel can answer complex questions using curated, expert-verified content. The audit logs are there to verify everything the AI does.

The harder change is mental: accepting that the compliance work that defined the profession for decades is becoming commoditized, and the future belongs to firms that embrace automation as the foundation for higher-value advisory services.

Elizabeth even suggests bringing these concepts into accounting education to attract new talent. Currently, tax courses focus on rules and calculations rather than strategy. After all, accounting is still “the language of business,” as Elizabeth was told as an undergraduate. The difference is that AI can now handle the grammar and spelling, freeing professionals to focus on telling the story.

The transformation won’t be easy, but it’s not optional. As Elizabeth learned when she left the profession out of frustration with mundane tasks, talented people won’t stick around if the work doesn’t engage them. The good news is that automation finally makes it possible to eliminate the drudgery and focus on what really matters: helping clients succeed.

Listen to the full conversation with Blake, Elizabeth, and Kirat for more insights on preparing your firm for the automated future of tax.

Streamlining Sales Tax Compliance: Exploring Avalara’s Managed Returns for Accountants

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Managing sales tax is one of the most challenging services to offer clients as an accounting firm.

Collecting sales information and filing tax returns traditionally involves a lot of work. It means logging in to multiple state portals, keying in sales data, and filing returns one at a time. With multiple clients filing in multiple jurisdictions each month, this quickly becomes unmanageable.

There’s also a big risk of making mistakes—if you slip up in one small way, it can lead to extensive notice correspondence and mounting penalties.

During an Earmark Expo webinar, hosts Blake Oliver and David Leary explored how modern compliance platforms such as Avalara’s Managed Returns for Accountants (MRA) allow you to expand your services without substantially increasing staff, risk, or costs.

Introducing a New Approach with Avalara

Avalara’s solutions aim to eliminate much of the repetitive manual work by consolidating data and automating return filings. John Sallese, Director of Strategic Accountant Solutions & Partnerships from Avalara showcased how Managed Returns for Accountants offloads the filing burden onto Avalara after the firm has reconciled the data. 

Here’s how it works:

  1. Data Collection and Review: Firms import or sync sales data from QuickBooks, Shopify, Amazon, or other systems into Avalara. The platform can also recalculate sales tax liability if needed.
  2. Approval by the Firm: After confirming the monthly numbers are correct, the firm marks each return “Approved to File.”
  3. Automated Filing and Payment: Once approved, Avalara files and remits payment on time, assuming responsibility for meeting deadlines, sending confirmations, and handling notices.

John noted that if the firm misses the approval deadline—usually around the 10th of each month—Avalara auto-approves to avoid late filings. 

As an added safeguard, if any Avalara-caused delay results in penalties or interest, Avalara covers those costs under the terms of service.

Two Distinct Service Models: MRA vs. Returns for Accountants

Avalara offers two different models for accounting professionals:

  1. Managed Returns for Accountants (MRA)
  • Firm’s Role: Gather and reconcile monthly data, approve liabilities.
  • Avalara’s Role: File returns, handle payments, and manage notices.
  • Key Benefit: Reduced risk for late filings and penalties, as Avalara takes over once data is approved.
  • Typical Cost: Ranges around $25–$30 per filed return (volume discounts may apply).
  1. Avalara Returns for Accountants (sometimes referred to as “ARA”)
  • Firm’s Role: Owns the full process—import data, finalize calculations, file, pay, and manage notices.
  • Avalara’s Role: Provides the software platform, automation tools, and supports advanced e-filing flows.
  • Key Benefit: Complete control and flexibility over the entire return process.
  • Typical Cost: Generally lower per return because the firm does more of the work.

Many firms adopt both solutions. 

Straightforward filings can go on the MRA model, where the firm approves data and lets Avalara handle the rest. 

Complex cases, such as back-filing multiple years, voluntary disclosures, or clients with inconsistent monthly data, might be better served with the RA model, which grants the firm end-to-end control.

Notice Management and Advisory Opportunities

In addition to filing returns, MRA includes comprehensive notice management. This means Avalara addresses notices from tax authorities and resolves them directly, relieving firms of much of the back-and-forth associated with sales tax inquiries. 

Firms also gain better visibility into potential advisory projects. “You’re not just filing returns,” John emphasized. “If you see clients calculating tax in states where they’re not registered, you can help them register or do a voluntary disclosure.”

Using these platforms can elevate the firm’s role from simple compliance processing to a strategic advisor, offering value-added services around taxability research, nexus studies, registrations, and more.

Implementation Considerations

John shared what to consider when you’re implementing Avalara MRA:

  • Data Integration: Ensure you can connect client systems (eCommerce, accounting, POS) to flow data automatically. This reduces manual entry and ensures more accurate filings.
  • Monthly Workflow: Clearly define who imports data, who reviews it, and when approval is due. MRA’s auto-approval protects against accidental late filing.
  • Client Onboarding: When setting up each client’s “filing calendar,” you’ll specify which returns need filing, the frequency, and any special state requirements. Avalara’s team verifies each setup to confirm accuracy.
  • Pricing Your Services: Whether you pass the per-return fees directly to clients or bundle them into a flat monthly charge, clarify the difference between MRA’s delegated model and RA’s self-service approach.

Elevate Your Sales Tax Practice

Sales tax compliance no longer has to be a necessary evil fraught with manual effort and risk. By choosing the right workflow model—either delegating filings to Avalara (MRA) or keeping them in-house (RA)—firms can scale sales tax services while maintaining appropriate oversight. The key is matching each client’s needs to the best approach.

Want to See a Live Demo?
Catch the full Earmark Expo session featuring Avalara, hosted by Blake Oliver and David Leary. You’ll see a real-time walkthrough of the platform and learn how to seamlessly integrate advanced compliance solutions into your firm’s existing workflow. 

Earn Free CPE

Visit earmark.app to watch the webinar and earn free NASBA-approved continuing professional education credit.

Tired of the January Scramble? Discover a Proactive Approach to 1099 Compliance

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No one brushes their teeth only the day before a dentist appointment and expects a clean bill of health—yet many businesses approach 1099 compliance in exactly this way. Every January, they scramble to collect W-9s, validate tax IDs, and rush out filings before the deadline. This last-minute frenzy creates stress and exposes companies to serious penalties if documentation is missing or incorrect.

In a recent Earmark Expo webinar, Gordon Walsh from Avalara demonstrated how modern automation tools like Avalara 1099 & W-9 can transform 1099 compliance from a reactive, annual challenge into a proactive, year-round process. By embracing real-time TIN matching and automated W-9 collection, businesses can significantly reduce compliance risks while freeing up valuable time during the year’s busiest season.

1099 Compliance Shouldn’t Be an Annual Fire Drill

Federal law requires businesses to collect W-9s before making payments to vendors. Despite this requirement, many firms still rely on manual processes: chasing vendors for handwritten forms, deciphering errors, and hoping everything arrives before January 31st. Without valid taxpayer information, businesses must withhold 24% for backup taxes—a situation that can create significant cash flow issues for vendors and administrative headaches for businesses.

“January’s 1099 season is really just where we feel the pain of all the things that we’ve done year-round that maybe didn’t get done,” explains Gordon Walsh. This reactive approach inevitably leads to costly, last-minute fixes and potential penalties.

The Power of Automated W-9 Collection

Traditional W-9 collection relies heavily on email and PDF exchanges—a system Gordon critiques saying, “There’s no other place in my life and business anywhere where I’m giving handwritten documents to people and expecting to do business with them.” 

Modern automation tools solve these challenges through:

  • Guided electronic forms with built-in validation
  • Intuitive menus that reduce classification errors
  • Centralized dashboard for tracking compliance status
  • Automated classification checks for 1099 requirements
  • Electronic delivery consent during onboarding

Having a system to collect vendor information ensures the capture of correct legal entity names, preventing downstream mismatches with IRS records.

Real-Time Validation: Preventing Costly Mistakes

Real-time TIN matching serves as the cornerstone of modern compliance systems. Instead of discovering mismatches after filing or receiving notices months later, Avalara’s system validates tax identification numbers during vendor onboarding. 

When mismatches occur, vendors can correct issues immediately, preventing:

  • Notices from the IRS
  • Mandatory 24% backup withholding
  • Time-consuming vendor follow-up
  • Potential penalties and fines

The system returns validation results directly to vendors during the submission process, allowing for immediate corrections. This preventative approach significantly reduces the risk of receiving IRS notices demanding backup withholding or corrections.

Streamlined Year-End Processing

The platform’s dashboard provides clear visibility into compliance status using a stoplight system:

  • Green: Ready for e-filing and electronic delivery
  • Yellow: E-filing ready but requires physical mail delivery
  • Red: Issues requiring immediate attention

For corrections, which are provided at no additional cost, the process has been simplified to a few clicks. Users can edit information directly in the system, with automatic filing of corrected forms to both state and federal authorities.

Integration and Accessibility

The system integrates with major accounting platforms like QuickBooks and includes bulk import capabilities for larger datasets. A global search function enables quick access to historical forms, allowing users to resend documents to recipients within seconds rather than searching through saved PDFs.

Historical data is maintained for five years, and the platform includes:

  • Secure document-sharing capabilities
  • State-specific compliance automation
  • Address verification through USPS
  • Multiple user access with role-based permissions

Pricing and Implementation

Rather than charging by the number of clients or users, pricing is based on total form volume. This tiered pricing model creates economies of scale—from several dollars per form at lower volumes to cents per form for high-volume users. While physical mailing incurs additional costs, the system encourages electronic delivery through early consent collection, helping businesses reduce expenses and administrative overhead.

The platform’s ease of use has earned it an NPS score of 79, reflecting its intuitive design and comprehensive feature set. With continued development, including a recently tripled development team, the system aims to expand its integration capabilities and streamline data flow between various business systems.

Through this combination of preventative validation, automated collection, and streamlined processing, businesses can transform their 1099 compliance from an annual emergency into a manageable, year-round process. 

Watch the full Earmark Expo webinar to see these automation tools in action and learn how to implement a proactive approach to compliance.