Legal departments get labeled the Department of "no." Block Chief Legal Officer Chrysty Esperanza and Spotify General Counsel Kevan Choset run theirs on the opposite premise: in AI, blocking is the riskier move. Between them, they lead legal and policy for two companies shipping AI to hundreds of millions of consumers, and both have concluded that the lawyers who will matter most in this era are the ones who understand the technology deeply enough to say yes with confidence.

Every AI feature that ships passes through a legal team first — which makes counsel either the bottleneck of this era or its quiet accelerant. Esperanza and Choset have each chosen the second job. Their playbooks, developed separately at a fintech and a streaming company, converge on the same moves: get close to the product, write the rules before regulators do and build with the very tools you’re being asked to approve.

Saying No Is the Higher Risk

Esperanza’s framing inverts the stereotype of the cautious in-house lawyer. “People that come in-house want to be enablers. They don’t want to be blockers,” she says. And with AI, the calculus has tipped decisively. “If you are saying no, that is a higher risk than saying yes, because you fall behind so fast. The technology is just compounding week over week.”

Choset’s version is structural: embed legal with the business so the guardrails exist before anyone asks. He explains the goal is to “give the yes with caveats before the question even comes up.”

There’s No Such Thing as an AI Lawyer

Neither of them accepts the premise that AI created a new legal specialty. When a product like AI DJ, the synthesized voice of a real person narrating your listening like a radio host, came through Spotify’s review, the team ran it through the same questions as any other launch. “We’re just going through sort of the same traditional legal issues that we’d look at for another product,” Choset says. “And it happens that the lens of this is AI.”

Esperanza agrees: “It’s gone from being more experimental to being embedded in everything that we do. So I don’t think of it as being an AI lawyer either.” Reviewing something like Money Bot, a Cash App product that surfaces trends and patterns for users, means using it to understand where the data comes from, where the human sits in the loop and when decisions get made. “That transparency with the customers, that’s what builds trust. That becomes that competitive advantage in the AI world,” says Choset.

Regulate Yourself Before Anyone Makes You

Both expect AI regulation to arrive as fragments across different states, countries and rules. Esperanza’s answer is architectural: “coming up with a framework that allows you to pivot, I think, is the most sustainable and durable way to approach things.”

Choset’s answer is to move first. Regulation is more predictable than it looks, because “regulators are human beings” reacting to familiar concerns — privacy, copyright, transparency. So Spotify writes its own rules ahead of the mandate: last fall it announced AI content policies, including one requiring anyone on the service to disclose who they actually are rather than vocally impersonate someone else.

The Chief Ethics Officer, With or Without the Title

The role runs past compliance into judgment. “The general counsel of the company is often sort of the chief ethics person at the company, sometimes with that title, sometimes without,” Choset says. He says legal training suits the moment because writing a good AI policy means teasing out principles: proposing a rule, stress-testing it against the case that breaks it and refining until it captures the actual harm.

Esperanza’s ethics run through the customer. In financial services, “there is such a big overlap between what intuitively you feel is right and what’s right under the law,” she says. “We’re not just thinking about what’s legal, but what will create a good consumer experience, which is oftentimes what’s the most ethical thing as well.”

Roll Up Your Sleeves and Build

Ask them what legal teams earlier in the AI journey should do, and the answer is hands on tools. “Adopt an AI mindset and think about problems through that AI lens. First, go to those tools and then just roll up your sleeves and build,” Esperanza says. The play has produced real infrastructure: Block’s team built a marketing legal tool that walks marketers through legal frameworks for influencer campaigns and social posts so routine reviews become self-service and lawyers keep their time for the complex ones.

Spotify built a similar tool, independently, and Choset reads that as a signal of how fast the ground has shifted. Five years ago, that software would have come from a SaaS vendor, but now, “you can just build it homegrown yourself quite quickly.” What holds most teams back is “a failure of imagination, where non-technical people don’t even understand what something could be capable of until they see it or play with it themselves.”

His parting advice strips the fear out of the buzzwords: “Think from first principles.” The actual AI issues are copyright, privacy, and employment issues, which he qualifies as the types of legal issues that come up across sectors. “Once you get your head out of that state of fear of the buzzwords, then you can actually, in a more methodical way, think through the issues.”

Based on a conversation in New York City with Chrysty Esperanza, Chief Legal Officer at Block, and Kevan Choset, General Counsel at Spotify, 2026 Runway AI Summit.