Most startups building AI for lawyers try to replace them. Spellbook is teaching AI to sound like them.
The Toronto- and Miami-based company just raised a $50 million Series B led by Keith Rabois at Khosla Ventures. It’s the latest milestone for a startup whose platform is currently used by more than 4,000 firms and legal teams across 80 countries.
In a statement, the company asserted that it is on pace to triple revenue in 2025.
Co-founder and CRO Daniel Di Maria, who’s based in Miami, has seen the shift firsthand. What started as a simple Microsoft Word add-in has turned into something much larger: a platform that lets lawyers review and draft contracts with AI that actually understands their voice. Di Maria built Spellbook alongside Matt Mayers and Scott Stevenson, both veterans of the tech world who saw how little innovation had touched legal work.
While most generative AI tools spit out boilerplate text, Spellbook is focused on precision. “We’re building the most data-driven contract review engine on the market – providing more relevant, substantive suggestions that you can defend with a counterparty,” the company said.
That’s possible thanks to the firm’s growing trove of real-world data. Spellbook’s upcoming Market Comparison feature, now in beta, lets lawyers see how their clauses stack up against similar deals by industry, size, or jurisdiction. It’s the kind of market intelligence usually reserved for top-tier firms, but now delivered in seconds.
The product also learns. “We’re enabling Spellbook to learn you and your organization’s preferences automatically over time,” the company explained. Each time a lawyer edits or approves a clause, Spellbook remembers, refining future drafts to sound less robotic and more like, well, them.
And Spellbook isn’t stopping at contracts. Its new product, Spellbook Associate, acts as a virtual legal assistant for transactional work: handling dataroom setup, document revisions, and complex workflows. The company says Associate is already becoming “as loved and used as our Word add-in product.”
The Series B funding will accelerate both product development and enterprise support. Half of Spellbook’s revenue now comes from large firms and corporate legal departments, prompting the team to add more integrations, stronger security controls, and scalable infrastructure.
Rabois’ involvement adds another layer of validation. A former lawyer himself, he joined Spellbook’s board as part of the deal.
For Di Maria, it’s also a Miami story. As more AI and B2B startups take root here, Spellbook stands out as an example of how global teams can use the city as a commercial and product hub.
If Spellbook succeeds, the next generation of lawyers might spend less time staring at redlines, and more time doing the thinking that can’t be automated.
Pictured at the top of the post: Spellbook co-founder/CEO Scott Stevenson with Khosla Ventures Managing Director Keith Rabois.
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