Robin AI Lays Off Staff as Growth Disappoints

Robin AI, the pioneering legal tech business, which was quick to combine genAI and human experts for contract review, is laying off staff after disappointing growth. Its recently hired new CTO has also left the company, although for other reasons, AL can confirm.

Artificial Lawyer spoke to Robin AI over the weekend following a report in Sifted that a ‘failed’ funding round had triggered staff cuts. UK-based Robin, which also has an office in New York, said that it could not comment at this time, but this site has confirmed the following:

• That a redundancy round is now taking place, and that other departures had already happened earlier this year.
• That this is due to lower than hoped for revenue growth. In March the company told AL that in 2024 it had 2x-ed its revenue to around $10m, after significant VC funding – including around $50m in 2024 and 2023. But, this investment does not seem to have translated into massive revenue growth in 2025.
• That it had previously reached a peak of around 200 staff, with the majority in the UK, but that the final number after the restructuring will be significantly lower.
• Tramale Turner, who joined earlier this year to replace the previous CTO, has already left Robin AI, after spending what seems to be less than 10 months at the company. The original CTO, James Clough, left for a role at another startup, and was also the co-founder of the business alongside CEO, Richard Robinson. A new CTO has now been appointed from within the company. Carina Negreanu, who was VP of AI, has now taken that role. However, Turner’s departure is understood not to be part of the lay-offs and was for other reasons.
• And, Ryan Heath, Robin’s Head of Communications, has also left the company.  

What is also understood to be highly likely is the following:

• That despite initial strong growth, and after using some of its funding money to buy part of LawGeex’s book of business of corporate clients, that Robin AI’s hope of continued rapid revenue expansion has stalled, at least over 2025.
• That although some fresh funding has probably been secured that the ambition to attract major investors for a larger funding round has not been successful.
• That the deal with Dye & Durham, a Canada-listed legal tech company focused on law firm operational needs, has likely not helped Robin AI as expected. The two companies announced a deal whereby the AI pioneer would target the Small Law segment, which Dye & Durham also serves. This was a strategic challenge, given that it mixed the messages over what Robin AI was doing and who it served. Meanwhile, Dye & Durham has its own problems, with changes at the top of its management and a 74% share price drop since the start of the year.

Why is this happening?

Well, we cannot know for sure about the internal goings-on inside Robin’s C-suite, no more than an outsider can really know what’s happening in anyone else’s marriage. So, let’s leave that to one side. But, what we can be sure of is that competition between legal tech companies selling AI-driven contract review software is at an all-time high. We have multiple players working in this segment now:

• CLM companies have adopted genAI and are expanding how they help inhouse teams review contracts.
• Inhouse teams simply tapping ‘raw’ LLMs to help with their contract work, (see the recent move by Juro to send its clients directly to ChatGPT, for example.)
• Some much larger companies, such as Workday now launching a range of AI tools for inhouse contract review needs.
• Newer companies such as Harvey, Legora and others have gained very significant funding and are seriously targeting the inhouse market.
• Older companies, some that started off in NLP/ML and others that have moved from other areas such as workflow automation, are also redoubling their efforts to capture inhouse contract needs.
• Hybrid AI ‘law firms’ from Crosby to Eudia are also absorbing market share and are growing very fast.
• Multiple ALSPs have begun to leverage AI now at scale.
• And then we have the law firm and Big Four ALSP arms, which surprisingly have not grown as much as they could, and in some cases have actually been pared back, but they still add to the overall mix.

All in all, that creates a tough market for vendors. And although there are in theory a lot of inhouse teams that could benefit from AI, with or without human experts on tap to help with accuracy and other needs, that the actual number of large companies that are bringing in this approach at scale is limited – for now. That in turn squeezes revenue growth opportunities.

Another aspect is the changing nature of the funds investing in legal tech. Whereas before it was smaller funds, making smaller investments and expecting lower growth, today we see the biggest funds in the world looking at legal tech and cutting very large cheques. But, the flipside is they want very rapid growth in return. Those that cannot meet those kinds of targets fall out of favour.

Overall, it would appear that a series of issues have affected Robin AI, from instability at the top with multiple CTOs – including losing a co-founder – just as the company was focused on growing, to doing strategically complex deals that perhaps made life more difficult. And then there are the macro issues noted above, i.e. huge pressure to grow by serving an inhouse client base that remains hard to sell to.

That in turn leads to the question of consolidation. Will some companies in this space, Robin AI included, choose to be acquired by a larger platform? We shall see.

Moreover, as things shake out across the end of this year and into 2026, we may well see one or two more companies in the same boat. Meanwhile, the more successful legal AI companies will no doubt seek to redouble their efforts and push ahead. One thing is for sure, the competition here is only going to get more intense.

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