Harvey makes a big exec hire as legal tech competition heats up

• Harvey is one of best-known, best-funded players in legal tech. Now it has to defend its lead.
• To pull it off, the legal AI startup has hired Anique Drumright as its first chief product officer.
• The C-suite addition comes at a make-or-break moment for legal tech as competition intensifies.

Harvey, the $8 billion legal software startup, is becoming a default vendor in Big Law. Now, with rival startups nipping at its heels and AI model providers moving closer to legal workflows, Harvey is bringing in a new executive to help defend its lead.

The company tells Business Insider it has hired Anique Drumright as its first chief product officer. In this role, she'll shape what Harvey builds next and how quickly it can ship. Drumright has held roles at Uber, TripActions, Loom, and, most recently, HR software startup Rippling, where she led the company's push into IT management software.

"Her slope of learning is very high," said Winston Weinberg, Harvey's chief executive. He described sending Drumright a lengthy Google Doc on the state of law firm technology and the day-to-day mechanics of legal work. She came back quickly with "really good product ideas," he said.

The C-suite hire comes at a critical moment for Harvey — and for legal tech more broadly. Law firms are pouring money into new software meant to help lawyers work faster and save costs. Clients are driving much of that spend. After seeing chatbots and virtual assistants transform their own operations, they now expect the same efficiency from outside counsel.

Those tools don't come cheap, and recent moves by the model providers themselves have complicated the picture. Anthropic's release last week of a contract-review tool sent ripples through the industry and led to a major sell-off of legal-research stocks. It raised a pointed question: If a foundation model can review contracts, on top of handling tasks across the rest of the organization, how much specialized legal software will firms still pay for?

Harvey sits at the top of the heap for now. The startup has emerged as one of the best-known and best-funded players in legal tech, with licenses at over half of the 100 largest US law firms. The company said it ended last year with more than $190 million in annual recurring revenue. And job postings reviewed by Business Insider suggest it is pushing into mid-market and smaller firms, a long tail of potential growth beyond Big Law.

Earlier this week, Forbes reported that Harvey is raising a new round of funding that would value the company at $11 billion, citing unnamed people familiar with the deal. A Harvey spokesperson declined to comment on the report.

Harvey's dominance comes with pressure. The company still needs to show lawyers its product can boost revenue, not just save hours. At the same time, competition is intensifying, from legal software startups like Legora and from OpenAI and Anthropic, the same companies whose technology powers Harvey's platform.

Weinberg said Anthropic's latest release doesn't change Harvey's product direction, but it does emphasize the need to move faster on shipping what makes the company distinctive. "Part of hiring Anique is to accelerate that," he said.

If the next fight is adoption, Drumright has put in the reps. She's spent years building products that ask people to change their habits.

At Uber, she worked in product and marketing as the ride-hailing giant scaled to billions of trips a year. Later, at Loom, she helped grow a product that nudged office workers away from meetings and long email chains, replacing them with screen-recorded video messages.

Drumright faces a similar challenge at Harvey, where the company has to convince reluctant lawyers, a famously luddite profession, to trade the familiar way of doing things for new tools. Those take time to use effectively.

"When something is new, even if it's powerful, it's still harder to do than the way you've always done it," she said. Her job, she said, is to make those new capabilities feel intuitive.

Drumright is the daughter of two lawyers, and she has seen firsthand how low-tech legal work can be. She remembers her mother siting on the couch, preparing for a deposition by speaking into a tape recorder.

Drumright starts on Tuesday. Her first weeks at Harvey will be spent on a listening tour, meeting lawyers using the product and legal teams deciding whether to buy it. "Legal is a very specific domain," she said, but the work starts with understanding how lawyers actually work today, and designing products that don't slow them down.

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