WeWork's former top lawyer is building an 'AI-native' law firm. Her model for client cost savings? TurboTax.
Founded by two former general counsels and backed by $4 million in venture funding, Covenant is betting that private markets are ready for a software-first approach to legal advice. Its tools use large language models to root through hundreds of pages of legal documents, raise red flags, and suggest stronger terms that are tailored to the investor's own playbook.
In the world of venture capital and other private funds, investors still pay law firms to tell them where and how to park their money. Endowments, pensions, and other institutional allocators rely on white-shoe lawyers to review limited partner agreements (LPAs), the legal backbone of a private investment fund. In theory, the bigger the law firm, the better the insight because it has seen more deals. But prestige doesn't come cheap, and neither does the billable hour.
Covenant is selling directly to institutional investors, not law firms, with the hope of cutting straight to the client and their bottom line.
Just as TurboTax made many Americans question whether they really needed an accountant, Covenent aims to give private market investors a reason to ask whether Big Law's invoices are still worth it.
The company tells Business Insider it's raised $4 million in a seed round led by Flybridge Capital Partners, with Neil Barsky, a former journalist and hedge fund manager, participating.
ReWork
Through the late aughts, Berrent was chief legal officer and co-president at WeWork, where she walked one of the trickiest tightropes in corporate law: counseling a high-flying, often chaotic startup and its mercurial founder, Adam Neumann. In 2019, former employees told Business Insider that Berrent was the person who tamed the chaos and protected the company as crisis after crisis unfolded.
She left WeWork in 2020. At first, Berrent set out to build a tool to help founders negotiate legal contracts. But she and Richard Perris, Covenant's cofounder and president, realized that opportunity was limited. Term sheets, offer letters, and non-disclosure agreements are relatively short, standardized, and not all that complex.
The bigger pain, Perris says, lives in private fund docs: LPAs and side letters, which carve out specific terms for specific investors. Their high-stakes fine print demands hours of expensive lawyer time. That's where large language models, Perris says, could "come in and crush this problem."
But before Covenant had a product or revenue, Flybridge made "a bet on Jen," says Jesse Middleton, who helped scale WeWork as an operator before becoming an investor at Flybridge.
Over the past 18 months, Berrent says Covenant has brought on around 45 customers, including endowments, foundations, pension plans, funds of funds, and sovereign wealth funds.
She declined to name any clients, but says monthly transaction volume has grown 50% since January.
Law Firm 2.0
Covenant is part of a new wave of law firms with the skeleton of a tech company and legal services layered on like tissue. Zach Posner, a venture capitalist who correctly called the legal tech boom in 2019, calls this category Law Firm 2.0. His fund is launching an accelerator to back the companies that compete head-on with law firms.
Zach Abramowitz, a consultant who advises law firms and legal departments on which software to buy, says he expects to see star attorneys peeling off from big firms to start their own tech-enabled practices.
To Abramowitz, the real upside isn't in building the next legal-tech unicorn like Harvey or Ironclad. It's in the long tail — what he describes as the Shopify phase of legal tech. Just as Amazon and Shopify unlocked a wave of entrepreneurs who built their own stores on top of those platforms, Abramowitz believes artificial intelligence will enable a surge of "bionic boutiques" that can generate significantly more revenue per lawyer.
"That's a much bigger opportunity," he said, "that inures to the benefit of more people."
Covenant joins a growing list of software companies with big backers and even bigger promises to strip the drudgery from legal work. But murmurs of a legal tech bubble are growing louder, especially as flashy tools like Harvey and Legora jockey for relevance in a still-cautious market.
For now, Covenant doesn't compete directly with those platforms, which sell into law firms and corporate legal departments. Instead, it occupies a lane closer to contract review tools like Luminance and Spellbook, which are also built for lawyers, not private market investors. To Berrent, the key distinction is that Covenant is selling legal services to customers who typically hire Big Law to do this work.
Berrent says she sees the next big opportunity not in AI for law firms, but in entirely new firms built around the tech. Call it counsel-as-a-service.
"Uber didn't sell software to taxi companies," she said. Instead, it redefined how people think about getting from point A to B. That's the kind of shift she's after.
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Time Magazine
21 minutes ago
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Yahoo
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The Most Anticipated Stock Split of 2025 May Be Announced Later Today
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CNN
an hour ago
- CNN
Trump to launch effort to ease Americans' access to their medical records — but privacy concerns loom
Donald TrumpFacebookTweetLink Follow President Donald Trump on Wednesday will make a fresh push to improve Americans' access to their own medical records, tasking dozens of major health and technology companies with solving an issue that has long bedeviled the federal government. The plan is expected to center on a pledge that roughly 60 companies will sign — including tech giants Microsoft and Oracle — to help develop new ways for more easily sharing patient data across the US's fragmented health care system, three people familiar with the matter told CNN. Trump is slated to tout the voluntary framework during a White House speech on Wednesday. Yet it remains unclear how quickly the companies can make progress on such a sweeping goal — and how the administration plans to hold them accountable for following through on the high-level, nonbinding commitment. The proposal may also spark pushback from privacy advocates who have warned that making patients' sensitive health data more widely accessible risks also making it less secure. The Centers for Medicare and Medicaid Services, which oversees the largest federal health programs, declined to comment on the details of the announcement. But in a statement, spokesperson Catherine Howden said the 'initiative aims to build a smarter, more secure and more personalized healthcare system — one that improves patient outcomes, reduces provider burden and drives greater value through private sector innovation and aligned federal leadership.' Bloomberg News first reported some of the initiative's details. The move represents the latest in a long line of attempts by the federal government to give patients greater access and control over their own health records, which often don't smoothly transfer from one health provider to another. Meanwhile, there's a newly added benefit for Silicon Valley, which has heavily invested in a growing array of consumer health, wellness and artificial intelligence startups that stand to gain from users being able to more seamlessly download their data and direct it to the apps of their choice. Amy Gleason, the acting administrator of DOGE and a former health tech executive, and Arda Kara, who worked at big data firm Palantir before joining the Trump health department, have led the medical records push, two of the people familiar said. The pledge comes two-and-a-half months after the health department issued a request for input from health and tech companies for improving the nation's 'digital health ecosystem.' Past Democratic and Republican administrations have made improving health record access a policy priority, arguing that it's critical to providing patients with better and more efficient care. But progress in Congress and within the federal government has been slowed by the thicket of technical challenges and privacy considerations surrounding Americans' most sensitive health data. Trump officials are planning to try a different route, relying on the private sector to make headway on those thorny problems ahead of any significant government intervention, the people familiar said. The tactic mirrors the hands-off approach the administration has taken on other top health priorities, such as encouraging food companies to voluntarily remove artificial dyes from products and getting insurers to commit to improving a 'prior authorization' process often blamed for delaying patients' care. But overhauling health records access will likely require broad collaboration among competitors across the health and technology industries, raising questions about whether the private sector will be able to agree on a host of minute details with broad implications. Plus, previous pushes have prompted significant concerns among privacy advocates and some parts of the health industry. Those groups worried that giving Americans greater ability to share their records will undermine federal efforts to keep their information private, making it easier for people to unwittingly expose their most sensitive data to companies with poor security or bad intentions, which could profit by selling that data.
