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Flex Secures $60M Series A to Automate Mid-Size Business Bookkeeping

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  Published in Business and Finance on Saturday, December 6th 2025 at 23:25 GMT by Reuters

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AI‑powered finance platform Flex lands $60 million to help mid‑size businesses cut costs and boost cash‑flow

By: MSN Money – 6 Dec 2025

An AI‑driven startup that is redefining bookkeeping for mid‑size businesses has just closed a $60 million round that will fuel the next phase of its growth. Flex, a New York‑based fintech that uses machine learning to automate financial operations, said on Thursday that its Series A round was led by Capital One Ventures, with co‑lead participation from Microsoft Ventures and a group of other strategic investors. The deal is expected to bring the company’s valuation to roughly $350 million, according to sources familiar with the transaction.

The company that is turning routine accounting into a data‑science playground

Founded in 2022 by former CFOs and AI engineers, Flex aims to make the day‑to‑day financial tasks that plague small‑to‑mid‑size companies—invoice processing, expense matching, cash‑flow forecasting, and compliance reporting—almost instantaneous. The startup’s flagship product is a cloud‑based platform that hooks into popular accounting ecosystems such as QuickBooks and Xero, and then uses natural‑language processing and deep‑learning models to extract data from PDFs, emails, and bank feeds. Within seconds, a dashboard is populated with the same ledger entries that would normally take a bookkeeper hours to enter manually.

Flex also claims to deliver “real‑time” insights on liquidity, revealing upcoming payment obligations, and flagging any anomalous spending that could hint at fraud or mis‑allocation of resources. “Our goal is to give every mid‑size business the same analytical depth that today only a handful of large enterprises enjoy,” Flex CEO and co‑founder, Elena Ruiz, said in a statement. “The cost of data‑science in finance should be a competitive advantage, not a luxury.”

In the year since launch, the platform has processed over 2 million invoices and recorded an annual recurring revenue (ARR) of $15 million, with a net retention rate above 120 %. “The product-market fit we’ve seen is undeniable,” said Ruiz. “We’re now looking to scale up sales, broaden our partner network, and invest in the next generation of AI capabilities that will help our clients not just react but anticipate market changes.”

Investors: a tech‑finance powerhouse

Capital One Ventures, the venture arm of the global bank, has a track record of backing fintech disruptors that streamline payments and data‑analytics. “We saw a clear opportunity to help a generation of businesses—especially those that grew during the pandemic—better manage their finances and stay cash‑positive,” said Mark S. Wilson, head of Capital One Ventures. “Flex’s AI technology aligns perfectly with our broader strategy of investing in fintech that drives financial inclusion and efficiency.”

Microsoft Ventures, the corporate venture fund of Microsoft, is particularly interested in AI tools that can integrate with its cloud and productivity ecosystems. “Flex’s solution can be a valuable addition to the Microsoft Cloud for Finance ecosystem,” said Susan M. Lee, director of strategic investments at Microsoft Ventures. “By combining our cloud infrastructure and data‑security standards with Flex’s AI engine, we can deliver a next‑generation finance experience for mid‑size companies.”

Other investors on the table included 6Point Capital, a venture arm focused on enterprise AI, and Accel, a well‑known global venture firm that has previously backed companies such as Atlassian and Slack. “Investing in Flex is a natural extension of Accel’s focus on AI‑driven enterprise solutions,” noted an Accel representative.

How the capital will be used

Flex plans to use the $60 million to accelerate three key priorities:

1. Product expansion – Building new AI modules that can automate tax filing, inventory valuation, and multi‑currency reconciliation. The company also intends to enhance its machine‑learning pipelines so the platform can handle more complex financial instruments and industry‑specific rules.

2. Go‑to‑market scaling – Doubling its sales team and investing in strategic partnerships with accounting firms and ERP vendors. By collaborating with firms that already serve mid‑size companies, Flex hopes to embed its platform as an “add‑on” solution that can be sold as part of a larger accounting suite.

3. Talent acquisition – Hiring data‑science talent to improve the accuracy of its NLP models and to develop new predictive analytics features that help clients forecast revenue and expenses under various market scenarios.

“We’re not just building software; we’re building a partner ecosystem,” said Ruiz. “The new capital will help us reach the thousands of mid‑size businesses that are still stuck in legacy accounting practices and need a modern, AI‑enabled way to manage cash flow and compliance.”

Why mid‑size businesses need AI finance tools now

According to a recent survey by the National Small Business Association, 78 % of mid‑size companies (those with 50–500 employees) report that manual bookkeeping is a top source of inefficiency and errors. In an era where supply‑chain volatility, rapid price changes, and complex regulatory requirements create financial uncertainty, these firms need real‑time data and actionable insights.

Flex’s AI platform addresses these pain points by reducing manual data entry, ensuring accuracy, and providing predictive analytics. “With AI, you’re no longer reacting to a problem after it happens; you’re anticipating it,” said Ruiz. “Our customers can now shift from firefighting to strategic planning.”

Looking ahead

Flex’s latest round places it among the fastest‑growing AI‑powered fintech startups. While the company still has its sights set on a broader market—potentially expanding into larger enterprises—it will need to navigate challenges such as data privacy compliance across different jurisdictions and competition from incumbents like Intuit and larger AI‑platform providers.

Nonetheless, the $60 million raise underscores investor confidence in the AI‑finance niche and signals that mid‑size companies are ready to adopt advanced analytics to stay competitive. As Flex scales, its story will likely serve as a case study in how machine learning can transform even the most routine aspects of business operations, giving medium‑sized enterprises the same advantage that technology has given big‑tech firms.