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Gunderson Dettmer has built its reputation as the leading law firm serving the innovation economy—handling more venture financing deals than any other firm in the world. For a firm that represents fast-moving startups and venture capital investors, speed and precision aren't luxuries; they're requirements. But achieving both while simultaneously giving clients the benefit of decades of collective experience presents a fundamental challenge: how do you make institutional knowledge, much of which resides in contracts, easily accessible at the time and place attorneys need it?

In 2021, Gunderson found a software partner equally committed to solving this problem: Draftwise, a legal technology startup founded by two ex-Palantir engineers and a former Clifford Chance lawyer.

"Draftwise helps transactional attorneys use their firm's best language to draft, review, and negotiate complex agreements directly inside of Microsoft Word," said James Ding, CEO and co-founder of Draftwise. "In Gunderson, we found a very highly regarded firm that was one of our earliest partners and champions. Their feedback has been instrumental in making Draftwise the product it is today."

Why Gunderson Chose Draftwise in 2021

Transactional lawyers rely on tried-and-tested language from precedents—it's how they ensure consistency, reduce risk, and leverage lessons learned from thousands of past deals. But the traditional process of finding the right clause from the right deal at the right time was inefficient. Attorneys would spend valuable time searching through document management systems, trying to remember which deal had that perfect indemnification provision or exactly how they handled a specific issue for a similar client six months ago.

"Our attorneys handle more transactions for fast-moving venture-backed companies than any other law firm in the world," said Naveen Pai, Chief Knowledge Officer at Gunderson Dettmer. "They were clamoring for a tool that would allow them to better leverage that knowledge and experience earned at the negotiating table. The speed with which we can serve our clients while helping them get the benefit of our collective experience as a firm is a top priority."

What set Draftwise apart was its sophisticated approach to organizing and structuring contracts and contractual provisions. Rather than requiring attorneys to leave their workflow, Draftwise brought the firm's institutional knowledge directly into Microsoft Word—right at the point of need when attorneys were actually drafting or negotiating contracts. The platform integrated seamlessly with Gunderson's document management system, making millions of documents searchable and accessible without disrupting how attorneys actually worked.

"I use Draftwise to find language I know I've used previously more quickly and efficiently," said Aaron Rubin, Partner in the Strategic Transactions & Licensing Group at Gunderson. "It helps me respond to clients faster and with the benefit of our experience. When you're negotiating a complex licensing agreement and you remember handling a similar issue two years ago, being able to surface that language in seconds rather than spending twenty minutes searching makes a real difference."

What impressed Gunderson equally was Draftwise's approach to collaborating with law firm customers. In an industry where software vendors often add client feedback to roadmaps destined for delivery quarters or years in the future, Draftwise operated differently. When Gunderson attorneys identified issues or suggested improvements, the Draftwise team would return within days with solutions in hand, iterating directly with attorneys to make the tool better. This responsiveness signaled that Draftwise understood the urgency and precision that transactional legal work demands.

Following a successful pilot, Gunderson signed a commercial agreement with Draftwise in 2021 and rolled out the platform to all its attorneys.

The LLM Revolution: Accelerating Impact in Legal Drafting

Gunderson's collaboration with Draftwise began before the mainstream adoption of large language models. In 2021, Draftwise was already tackling the fundamental challenge of helping attorneys efficiently access and use precedent language—organizing contracts in sophisticated ways and surfacing the right clauses when lawyers needed them. The platform had built the critical infrastructure to connect to document management systems, drafting tools that understood contract structure, and made institutional knowledge directly accessible from within Microsoft Word.

When generative AI burst into public consciousness in late 2022, Gunderson was uniquely positioned to understand its potential. The firm had been experimenting with LLMs for extracting insights from contract language since 2021—more than a year before ChatGPT's public release. This early adoption gave Gunderson invaluable experience in how AI could be applied to legal practice and helped the firm build an AI-ready culture among its attorneys.

"We saw the power of LLMs early on and became a leader in the legal industry at deploying the technology," said Joe Green, Chief Innovation Officer at Gunderson Dettmer. "What's exciting is how well-positioned Draftwise has been to leverage these capabilities. The problems they originally set out to solve with their initial product—helping lawyers access and use their firm's precedent language and collective knowledge—are the types of use cases that LLMs, with their facility with language, are particularly well-suited to enhancing. The Draftwise team understood that opportunity very quickly and had the engineering chops to make the best of it."

For Draftwise, the LLM revolution represented not a pivot but an acceleration. Large language models became a powerful enabling technology that could dramatically improve how attorneys interacedt with precedent language. Rather than just searching for clauses, attorneys can now ask questions, identify issues, and even create initial markups of draft contracts based on their firm's actual precedent and preferred positions. LLMs now serve as an accelerant for Gunderson's subject-matter experts—supercharging productivity while retaining the human judgment that clients value most.

By 2025, Draftwise had evolved its platform to include sophisticated agentic AI capabilities—advanced AI that can perform complex, multi-step legal tasks. These capabilities include validating contracts against term sheets, providing tailored clause recommendations based on a firm's past deals, and offering strategic contract guidance informed by historical practices.

Drafting Tools and Our Agentic Future

The collaboration between Gunderson and Draftwise has evolved into something deeper than a typical vendor-customer relationship. Gunderson has been a design and development partner from the outset, helping Draftwise refine and test new capabilities that represent the next generation of legal technology.

What excites many at Gunderson is Draftwise's emerging agentic capabilities—AI that can take high-level instructions and execute multi-step tasks autonomously. Attorneys can now ask questions like "What other reps and warranties might my client want in this agreement?" or "Make my clause more buyer-friendly based on recent similar deals," and receive substantive, precedent-based responses marked directly into the document for the attorney’s review. This process would have previously required extensive manual research and drafting.

The firm's ability to encode its knowledge of the market and legal practice into playbooks and other tools accessible to Draftwise's AI agent creates the potential to make attorneys both faster and more effective at retrieving collective knowledge. Rather than requiring attorneys to become prompt engineers or learn complex new interfaces, agentic AI allows them to interact with technology more naturally.

"I'm excited about the potential of the agentic capabilities because it's a natural way for me to interact with the software—similar to how I would interact with a junior lawyer," said Jeff Stricker, Partner in the Corporate practice group at Gunderson. "I can give high-level instructions and get a response for me to review that leverages our firm's past experience to execute the task in a way that's consistent with how we practice."

This represents a meaningful shift in how legal technology can enhance complex professional work-product rather than simply automate routine tasks. The AI isn't replacing the attorney's strategic thinking or client relationship; it's accelerating the mechanical aspects of drafting and research so attorneys can focus more on the substantive legal analysis and counseling that clients value most.

Looking Forward

Four years into working together, Gunderson and Draftwise continue to push the boundaries of what's possible when sophisticated legal expertise meets cutting-edge technology. Draftwise now works with more than half of the Vault 10 law firms, dozens of Am Law 100 firms, and multiple Fortune 500 organizations across North America, EMEA, and APAC.

For Gunderson, this collaboration exemplifies the firm's broader innovation strategy: identifying technologies that align with how attorneys actually work, collaborating with software companies who are genuinely responsive to legal practice needs, and deploying tools that enhance rather than replace professional judgment. The result is a firm better equipped to serve the fast-moving clients of the innovation economy—companies and investors who expect their legal counsel to move at their pace without sacrificing quality or insight.

As Joe Green reflects on the journey, what stands out isn't just the powerful technology but the way way of working together: "When you find a technology partner who truly understands legal work and is committed to iterating based on real-world usage, you can build capabilities that are far more valuable than just buying software off-the-shelf. You can fundamentally change how knowledge flows through an organization—and that's exactly what we've been able to do with Draftwise."