Jen Berrent is the Founder and CEO of Covenant, a specialized law firm combining data, technology and AI. Before launching Covenant, Jen was Chief Legal Officer and Chief Operating Officer at WeWork, where she helped scale the company into a global powerhouse. Earlier in her career, she was a partner at WilmerHale, leading the New York emerging company practice. Jen’s work sits at the cutting edge of law and innovation, reshaping how legal services are delivered.

The era of artificial intelligence fundamentally disrupting legal services has arrived. The traditional legal industry is ripe for transformation.

Please tell us about the product or service that Covenant offers.

Covenant is an AI-powered law firm purpose-built for private market investors. We combine advanced AI with deep legal expertise to deliver the same high-quality legal analysis as traditional law firms. Our core offerings include Limited Partnership Agreement (LPA) reviews with 2-business day turnaround, automated Most Favored Nation (MFN) elections, Form ADV analysis, NDA reviews and Data Extraction. Through our secure web portal, clients can access personalized document databases, compare terms across drafts and managers, and export relevant data. We serve leading endowments, foundations, sovereign wealth funds, fund of funds, and other institutional allocators.

Coming from WeWork as COO and Chief Legal Officer, what did you observe about legal inefficiencies in private markets that convinced you this was the right problem to solve?

At WeWork, I witnessed firsthand how traditional legal processes couldn’t keep pace with the speed and scale of modern business. In private markets specifically, we saw institutional investors navigating complex legal documentation – hundreds of pages per deal, months-long review cycles, and astronomical legal fees that created real barriers to efficient capital deployment. The inefficiency was staggering: junior associates learning on clients’ time and dime, redundant manual reviews, and no systematic way to leverage insights from past transactions. We realized that private market investors needed a solution that could deliver institutional-quality legal work at the speed of business.

What differentiates Covenant from other AI-native law firms?

Covenant is laser-focused on private market investors with purpose-built tools for their specific needs. Our technology stack combines multiple AI models with human verification, ensuring both speed and accuracy. We maintain SOC 2 Type II certification with strict data protections including zero client data training, no data retention, and full anonymization. Most importantly, we’re not just a tech company with legal features – we’re experienced lawyers who understand the nuances of private market transactions and have built technology to solve real problems we’ve personally faced.

You use multiple AI models rather than depending on a single one, while most companies pick one and optimize. What’s the strategic advantage of this approach?

Our multi-model approach is a deliberate strategic choice that delivers three key advantages. First, it eliminates single points of failure – if one model has limitations or experiences downtime, our system remains robust. Second, it allows us to leverage the unique strengths of different models for different tasks, optimizing for accuracy rather than convenience. Third, and perhaps most importantly, it enables us to rapidly adopt the latest AI innovations without being
locked into a single vendor’s development cycle. This flexibility means our clients always benefit from cutting-edge capabilities while maintaining the consistency and reliability they require for mission-critical legal work.

Traditional law firms charge premium rates for expertise. How do you deliver “the same high-quality results at a fraction of the cost” without compromising on accuracy or judgment?

We achieve this through a fundamental reimagining of how legal work gets done. Traditional firms have massive overhead. We’ve eliminated these inefficiencies by building AI systems that handle the heavy lifting of document review and analysis, allowing our senior lawyers to focus on high-value judgment calls and strategic advice. Our AI doesn’t replace legal expertise – it amplifies it. Every AI output undergoes human verification by experienced attorneys. By automating the time-intensive but routine aspects of legal review, we can deliver work 5x faster while maintaining the accuracy standards our institutional clients demand. The result is premium quality at a sustainable price point.

You’ve built tools specifically for LPs—LPA reviews, MFN elections, due diligence. Why start with the buy-side rather than targeting GPs or the broader legal market?

We started with LPs because they face a unique set of challenges that are perfectly suited to our AI-powered approach. LPs review hundreds of complex legal documents across multiple fund investments, often with limited resources and tight timelines. They need consistency, speed, and the ability to extract insights across their entire portfolio – exactly what our technology delivers. Additionally, LPs are sophisticated repeat players who understand the value of innovation and efficiency. The LP market alone represents a massive opportunity – these institutions deploy trillions in capital and need modern legal infrastructure to match their ambitions.

You’re building what sounds like a hybrid between a law firm and a tech company. What kind of culture are you creating, and how do you attract both top legal talent and AI engineers?

We’re creating a culture of intellectual curiosity where lawyers and technologists collaborate to solve complex problems. Our team includes both seasoned legal professionals who’ve worked at the highest levels and innovative technologists who are passionate about transforming an entire industry. We attract top talent by offering something unique: for lawyers, the chance to practice at the cutting edge of their profession; for engineers, the opportunity to build AI systems that have immediate, measurable impact on multi-billion dollar transactions. We’re not just using technology; we’re fundamentally reimagining how legal expertise is delivered.

What’s the biggest misconception people have about AI in legal work, and how do you address those concerns with clients?

The biggest misconception is that AI in legal work means compromising on quality or security for the sake of speed. Many clients initially question accuracy, data privacy, or whether AI can handle the nuanced judgment calls that complex transactions require. We address these concerns head-on with complete transparency. First, we demonstrate that our AI-powered results undergo rigorous human verification, we’re augmenting human expertise, not replacing it. Second, we’ve invested heavily in security, achieving SOC 2 Type II certification with zero client data training, no data retention, and full anonymization.

If there’s one thing you want the private markets community to understand about this next phase of legal technology, what would it be?

The era of artificial intelligence fundamentally disrupting legal services has arrived. The traditional legal industry is ripe for transformation. But this isn’t about technology for technology’s sake. It’s about empowering private market investors to move at the speed their business demands, to extract insights from their entire portfolio systematically, and to make better-informed decisions faster. The firms and funds that embrace this shift have a significant competitive advantage.

What are some milestones you plan to achieve in the near term?

With our $4 million seed funding from Flybridge Capital Partners and Neil Barsky, we’re focused on scaling to meet the growing client demand while continuing to deepen the capabilities of our platform. To accelerate this work, we’re actively iring across engineering and legal, ensuring we have the expertise needed to build with both speed and precision.

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