Is AI Really Reshaping Legal Departments, Or Have We Been Here Before?

The legal industry has gone through several moments where companies were confronted with the realization that they needed a different kind of lawyer than they had before. During the SaaS boom, fast-growing companies rushed to hire commercial attorneys who could support sales teams and contracts. When fintech and crypto surged, the focus shifted almost overnight toward regulatory lawyers and those with government experience and relationships.

Now, as companies navigate the opportunities and challenges of the new AI frontier, there is an added complication: there is no deep bench of truly experienced AI lawyers yet. Many attorneys currently inside major AI companies have only been there for months, not years, and are still gaining ground-level experience. They aren’t necessarily looking to take their expertise elsewhere quite yet.

The more useful question for legal departments right now may not be, “Who can bring me direct AI experience?” but rather “What other industries have navigated similar periods of expansion and uncertainty before, and what types of lawyers proved most valuable during those transitions?” Reflecting on these moments could provide valuable lessons to companies looking to navigate the AI boom now.

So, what types of lawyers are best equipped to support legal departments with AI?

So far, most AI companies are not immediately prioritizing regulatory or privacy-heavy legal hires. Instead, many are hiring commercial and product-focused attorneys first, similar to what happened during the SaaS expansion phase.

We see this clearly in early-stage startups, who often prioritize commercial and product counsel as their first legal hires, often those with three to six years of experience. Just as SaaS-era hiring centered heavily on industry-specific capabilities such as sales support, contracting and efficient deal execution, today’s AI companies require legal professionals who understand commercial norms in vendor and customer contracting, procurement and production. At this stage, keeping pace with revenue generation and product deployment takes precedence over a privacy-first or regulatory-heavy legal build.

James Toy, chief legal officer at Articore who operates the global creator marketplaces Redbubble and TeePublic, notes that this shift with AI has made them reposition what they’re looking for in team members. "We want lawyers who are genuinely trying to transform how in-house legal teams operate on a fundamental level," Toy explains. "What we look for goes beyond just using AI to speed things up or layer it onto existing workflows." For Toy, the ideal candidate is focused on building an autonomous legal function rather than just settling for marginal gains.

What transferable skills should companies be on the lookout for?

Because AI-specific legal experience is still limited, legal departments are increasingly focused on adjacent skill sets rather than direct experience. The emphasis is shifting toward lawyers who can operate in ambiguity, understand risk profiles, and build their own processes in a quickly evolving environment. This means prioritizing strong commercial attorneys who can quickly adapt to evolving regulatory expectations and business models.

The reality is that “AI experience” is still not a meaningful hiring filter at scale. GCs are realizing this fact and adjusting their tactics accordingly. Instead of mandating artificial constraints in formal role descriptions, companies are choosing to dig into skills more informally during conversations with candidates, looking past buzzwords to evaluate lawyer’s fundamental adaptability.

When evaluating candidates’ skill sets, Jessica Shor, general counsel at software company Contentstack, actively looks for a proactive attitude to learn and experiment. “I believe AI’s current utility in legal is still evolving compared to other sectors. Iassess fluency by asking candidates how they use AI, what specific challenges it has helped them solve, and how much time they have saved.” Shor said. “Ultimately, I am looking for candidates who demonstrate a willingness to lean in and use AI more creatively than I do.”

How should legal departments structure around AI—before they make the hires?

Time and time again, we hear hiring managers say: “We want somebody who can role up their sleeves.”

But before a GC can hire well, they need to establish an internal strategy and determine what will AI be used for. Is it primarily a tool to help day-to-day productivity and efficiency, or is it something more transformational for the business? The answer to that question can dictate the type of person you should hire for, whether you need a builder for something from the ground up or a manager for existing systems to drive productivity.

There needs to be alignment with what the person has done and how they think about AI and what your business goals are. In interviews, they should ask—what have you built or changed using AI? Lawyers who have meaningfully restructured their own workflows are different than those who occasionally use a chatbot for drafting or research.

Andrew Woods, general counsel of PubMatic, points out that a robust AI strategy actually reshapes the necessity of scaling headcount in the first place. "You shouldn't need to add headcount to execute an AI strategy," Woods argues. "You should be using AI to raise the ceiling on what your current team can accomplish." Reflecting on past tech waves, Woods cautions against falling into the trap of hunting for "purple-unicorn" resumes with hyper-specific domain experience that rarely transfers well.

While AI and the hype around the industry is new, this market shift is entirely familiar, and the learned lessons lie in finding adaptable and skilled attorneys rather than chasing non-existent AI resumes, as was done in previous shifts with booms impacting the legal industry.