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Chatbots Behaving Badly™

When Tech Titans Buy the Books - How VCs and PEs Are Turning Accounting Firms into AI Trailblazers

By Markus Brinsa  |  June 17, 2025

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The New Face in the Accounting Office

Late on a Tuesday night in Tampa, Florida, an audit team at a local accounting firm wrapped up their tests hours earlier than usual. The difference? They had a new helper working around the clock – not a junior associate, but an artificial intelligence tool trained to scrutinize invoices and draft audit memos. One partner marveled that the AI had saved the staff hundreds of hours that month in routine testing, freeing them to focus on client advice and complex judgment calls. This quiet leap in productivity was not a fluke. It was the result of an ambitious experiment: a venture capital-backed company had swooped in to acquire the firm and supercharge it with cutting-edge AI.

Scenes like this are playing out across the accounting world. In an industry long viewed as steady and traditional – sometimes to a fault – an infusion of Silicon Valley ethos is shaking things up. Venture capital (VC) and private equity (PE) firms have started buying stakes in accounting practices and layering in technology in a bid to transform how the books are kept and audited. It’s a trend few in either camp foresaw a decade ago: tech investors and spreadsheet mavens becoming partners. But now it’s happening at a brisk pace, driven by a tantalizing prospect – that with enough data and AI muscle, even a 50-person regional accounting firm can grow like a tech startup.

Beyond Bean Counting - Why Investors Are Piling In

At first glance, accounting might seem an unlikely target for venture capitalists and dealmakers. This is a field known more for its careful steadiness than for disruptive leaps. Yet that is precisely what makes it attractive. Accounting firms offer something rare in the business world: reliable, recurring revenue. The annual audits and monthly bookkeeping engagements generate fees with metronomic regularity – an “annuity-like” income stream that hums along year after year . To investors used to the rollercoaster of startups, those steady cash flows look a lot like a subscription business, minus the volatility.

But stability is only part of the formula. Private equity and VC backers see huge untapped potential for growth in these venerable firms. The accounting sector remains highly fragmented, with tens of thousands of small partnerships serving local clients. For an investor with deep pockets, that fragmentation spells opportunity: roll up dozens of smaller firms into one tech-enabled platform, and suddenly you have scale. Consolidating peers under one roof can bring economies of scale and shared infrastructure, from unified software systems to centralized compliance processes. A larger platform firm can also offer new services (think AI-driven analytics or strategic advisory) on top of traditional audit and tax work, tapping into higher-margin opportunities. In essence, an accounting firm that embraces technology and breadth can start to behave a bit more like a high-growth enterprise, without losing that stable base of recurring fees.

Crucially, technology – especially AI – is the lever to make this possible. Forward-looking investors argue that buying an old-school firm and simply slashing costs isn’t a winning play here. The real prize is enhancing productivity and capacity. As one venture investor involved in these deals put it, unlike a typical leveraged buyout that “relies on debt funding and cost cutting,” this strategy “focuses on adding software and AI-oriented productivity improvements”. An AI-augmented accounting practice can take on far more business with the same human headcount. Instead of replacing the accountants, the new owners want to arm them with algorithms. If each accountant can serve two or three times as many clients thanks to automation, revenue climbs accordingly . It’s a vision of tech-enabled growth rather than just expense trimming.

That vision also addresses a looming talent crunch. Fewer young people are pursuing accounting careers in recent years, creating a shortage of experienced CPAs. At the same time, many senior partners are nearing retirement and looking for ways to cash out after decades in practice. Outside capital offers a solution to both issues. With an injection of funds, firms can invest in AI and other technologies to do more with fewer staff, easing the pressure of labor shortages. And those retiring partners? Selling a stake to a PE fund can unlock value from the business that might otherwise take decades to realize under the traditional partnership model. As one industry observer noted, “Accountants need cash to deploy AI, retain talent, and overhaul aging partnerships. PE is drawn to the fragmented sector’s stable cash flow, loyal customer base, and rosy financial projections”. In short, tech investors see a chance to modernize a vital industry – and to profit handsomely by doing so.

AI Enters the Workflow and Rewires the Accounting Engine

So, what does it actually mean to transform an accounting firm with AI? It’s not as simple as installing a new software package. Rather, it involves weaving intelligent automation into nearly every nook of the firm’s operations. Picture the traditional workflow of an accountant, and you can find places where AI can lend a hand. Sorting and categorizing expenses – once a tedious task of rifling through receipts – can be largely automated by machine learning models trained on millions of transactions. These models learn to recognize whether a $50 charge was for office supplies or client entertainment, and they get faster and more accurate with time. Similarly, AI-powered anomaly detection systems now scan ledgers for irregularities, flagging transactions that deviate from the norm so humans can investigate.  In truth, there isn’t a single silver bullet AI that does it all. As one venture capitalist quipped, there’s “not some magic AI accounting product today that automates the audit function or the tax function or the bookkeeping function” – instead, dozens of startups are tackling each piece of the puzzle. Collectively, these advances are moving the needle. Instead of sampling a few entries in an audit, an algorithm can check every single one, at lightning speed, in the hunt for errors or fraud.

The promise of AI extends beyond back-office number crunching. It’s also about delivering richer insights to clients, faster. Modern accounting firms are using predictive models to forecast financial trends for their clients – projecting cash flows, analyzing risks, and even running ‘what-if’ scenarios on the fly. A decade ago, a small business might get a quarterly report with backward-looking figures. Today, an AI-enhanced firm can provide real-time dashboards and forward-looking analysis, with software pulling data from bank accounts, sales systems, and beyond. When there’s a sudden spike in expenses or a dip in gross margin, the AI can alert both the accountant and the client in real time, often with a natural-language explanation of the cause. Imagine a dashboard that doesn’t just show your numbers but also tells you why they changed – that’s the level of service these transformations aim to achieve.

Even the craft of audit and tax, long seen as requiring human judgment, is getting a boost from AI. Take audit, for example: one of the time-consuming tasks is writing up summaries and memos of all those testing procedures and findings. At firms like Crete, the tech team has built tools to automate parts of that documentation process. The AI combs through workpapers and drafts memos, which auditors then refine. According to an executive at one Crete-owned firm, this alone saved his team hundreds of hours in audit prep each month. It doesn’t replace the auditor’s judgment, but it accelerates the grunt work to let them focus on higher-level analysis. On the tax side, AI is being used to parse through piles of regulations and client data to identify optimal strategies and flag compliance issues, a job that would have taken an army of tax juniors weeks to do.

Crucially, the goal of these AI deployments isn’t to oust the humans – it’s to elevate them. Jake Sloane, co-founder of Crete Professionals Alliance, emphasizes that they’re not aiming to replace accountants with chatbots or algorithms. Instead, it’s about freeing up human professionals to do what machines can’t: building relationships, exercising judgment, and providing strategic counsel. As another investor put it, the idea is not to cut people but to let them “do two-to-three times the work” by letting AI handle the drudgery. In practice, that might mean an accountant who used to spend Mondays chasing down missing receipts can now spend that time advising a client on improving their cash reserves, while an AI assistant takes care of the chase. The firm’s capacity grows without sacrificing quality. In fact, by automating rote tasks, many expect quality to improve, since algorithms are less likely to overlook stray details and can enforce consistency in processes.

Building Scalable, Synergistic Firms

From the investor’s perspective, these AI-fueled accounting firms aren’t just marginally better versions of the old model – they’re a chance to build something with tech-like scalability. In a traditional firm, revenue is bound by how many hours your accountants can work. But once you introduce automation, that ceiling lifts. Suddenly, a midsize firm can think bigger: take on far more clients, spread across geographies, without a linear increase in headcount. Crete Professionals Alliance, backed by Thrive Capital, is a case in point – in just two years since its 2023 founding, it has acquired over 20 firms and grown to 900 employees across 17 offices. Armed with custom AI tools developed in partnership with OpenAI, Crete’s network is aiming to serve clients at a scale that would have seemed impossible for its component firms on their own. Thrive’s team didn’t just inject money; they brought in tech experts and connections (Thrive, notably, was an investor in OpenAI itself) to build AI models tailored to accounting needs. That kind of synergy – using a VC’s technology know-how to turbocharge a very traditional business – is a key part of this play.

Private equity players are pursuing a similar playbook, albeit with their own twist. Consider the example of Carr, Riggs & Ingram (CRI), a large regional accounting firm. When private equity firm Centerbridge decided to invest in CRI, they brought along Bessemer Venture Partners as a co-investor specifically to infuse AI expertise . The goal? To turn a $500 million-revenue operation into a billion-dollar one within a few years by aggressively deploying AI for efficiency and new services. It’s essentially treating an accounting firm as a platform ripe for a tech overhaul. Similarly, when Grant Thornton UK sold a stake to PE firm Cinven and when PKF O’Connor Davies took on an investment from two funds, a big part of their plans involved upgrading technology and analytics capabilities. These investors aren’t content with steady 5% annual growth – they want to engineer leaps in scale and profitability, the kind of jumps tech companies achieve by leveraging software.

Owning an accounting firm can also create synergies across an investor’s portfolio. A private equity fund that has dozens of companies under its umbrella might channel some of its financial work to its in-house accounting platform – boosting that firm’s client base while potentially offering those portfolio companies a tech-augmented service. Even beyond direct business referrals, there’s knowledge sharing: an AI tool or best practice developed in one firm can be rolled out quickly to others in the fold. The roll-up strategy itself builds a network effect: each additional firm acquired brings new specialists and new datasets that can improve the AI models for everyone. There’s a vision of creating an end-to-end ecosystem, where a client might get bookkeeping, tax planning, audit, and CFO-level advice all from one provider that feels as nimble as a fintech app. It’s no wonder one VC described AI-enabled roll-ups as a whole new asset class of investment emerging in 2024 and beyond.

Of course, this grand plan remains a work in progress. Even the investors driving it acknowledge that many AI tools are still in early stages. One backer admitted there’s speculation involved – the bet is that an “AI tailwind” will provide the upside to turn a good deal into a spectacular one. And not everyone in the industry is convinced: skeptics point out that if AI makes routine accounting work too efficient, it could also drive prices down and commoditize services. The competitive landscape isn’t standing still either; traditional firms are upping their tech games, and the Big Four accounting giants are pouring billions into AI to defend their turf. Nonetheless, the flurry of activity in the past couple of years shows a genuine conviction that something big is brewing at the intersection of accounting and AI. If the experiment succeeds, the payoff could be substantial – not just for investors, but for an industry that could evolve from the stereotype of bean counters to something closer to financial innovators.

Data Privacy and Regulatory Scrutiny

Amid the excitement, these tech-driven makeovers of accounting firms aren’t without concerns. Two big issues stand out: data privacy and regulatory oversight. Accounting firms deal with troves of sensitive financial information – tax returns, payrolls, confidential ledgers – the kind of data clients entrust under strict professional standards of confidentiality. Introducing AI into the mix raises hard questions about how that data is handled. If an AI tool is cloud-based or operated by a third-party provider, what guarantees are there that client information won’t leak or be misused? Industry guidelines urge firms to be extremely cautious: for instance, CPA firms are advised to “prohibit the sharing of confidential client information with generative AI tools” unless proper safeguards are in place . In practice, this means investors building AI-fueled workflows must invest in security and possibly develop private, in-house AI systems rather than sending data to open platforms. The last thing a newly tech-forward firm needs is a breach of client trust or a violation of data protection laws.

Then there’s the question of oversight from regulators. Audit, in particular, is considered a public trust – it underpins the credibility of financial markets. When outside investors enter the picture, watchdogs start to ask questions. Could profit pressures from a private equity owner lead to compromised audit quality? Could conflicts of interest arise if an investment firm’s portfolio companies are also clients of the accounting firm? These concerns are not hypothetical. In the US, officials have fretted that the influx of private equity could erode auditor independence and rigor. Across the Atlantic, the UK’s accounting regulator went so far as to require firms to consult with authorities before taking PE investments, to ensure the public interest is safeguarded. The advent of AI adds another layer of complexity: regulators will want to know how automated analyses are being used in audits and whether humans remain in control of critical judgments. Firms on the cutting edge are acutely aware of this scrutiny. Many are taking steps to separate their audit divisions from the parts of the business that have external investors, and to document how AI tools are validated and overseen. In short, they’re keen to show that while the tools are new, the bedrock principles of accuracy, independence, and confidentiality remain firmly in place.

Ultimately, the marriage of private capital and accounting technology is testing the balance between innovation and trust. The potential upsides – greater efficiency, deeper insights, more value for clients – are exciting. But the guardians of the financial system will not tolerate any slipping of standards. The new breed of tech-enabled accounting firms will have to prove that they can achieve tech-like growth without tech-like recklessness. If they succeed, they might not only make their investors wealthy but also help rejuvenate the accounting profession for a new era. If they fail, they’ll serve as cautionary tales of when moving fast and breaking things met an industry where trust is paramount.

About the Author

Markus Brinsa is the Founder and CEO of SEIKOURI Inc., an international strategy consulting firm specializing in early-stage innovation discovery and AI Matchmaking. He is also the creator of Chatbots Behaving Badly, a platform and podcast that investigates the real-world failures, risks, and ethical challenges of artificial intelligence. With over 15 years of experience bridging technology, business strategy, and market expansion in the U.S. and Europe, Markus works with executives, investors, and developers to turn AI’s potential into sustainable, real-world impact.

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