In this episode of the Technically Legal podcast, Yelena joined host Chad Main to talk about why legal tech is growing, where she’s seeing real traction, and how founders can actually earn investor conviction in a market known for long sales cycles and legacy behavior.

Yelena’s path to venture started in investment banking and entertainment finance before she began backing early-stage software companies. Today, she focuses on early-stage investments across infrastructure, applied AI, and enterprise SaaS, including legal tech. In this conversation, she shares what it takes to stand out in a category that’s both complicated and full of potential.

Key Takeaways:
Obsessed founders win.
Legal is a tough market. Procurement takes time. Workflows are specific. And many buyers don’t want to change how they work. That’s why Yelena looks for founders who’ve done the work to understand what’s broken, and who they’re building for.

“The best founders are obsessed with their customers’ problems, not just their own solutions.”

AI is only useful if it fits how lawyers already work.
There’s no shortage of hype around AI in legal. But Yelena is focused on practical applications, tools that actually integrate into a lawyer’s day-to-day, not ones that require major behavior change.

“AI is exciting,” she says, “but it has to fit into the way lawyers actually work, or it won’t get adopted.” That bar is especially high in legal, where time, risk, and precedent matter. Tools that automate tedious tasks, without complicating workflows, are most likely to see adoption.

Deep domain experience > a law degree.
Founders don’t need to be lawyers. But they do need to understand them. Some of the best legal tech companies Yelena’s seen are built by outsiders who’ve spent time listening, testing, and refining solutions that legal professionals actually want.

It’s about respecting the complexity of the space, not assuming tech alone can solve it.

Access to justice is a business opportunity, too.
While much of the conversation in legal tech centers on enterprise sales, Yelena also sees major potential on the consumer side. There’s still a massive gap in affordable, accessible legal services—and founders building in this area have a chance to drive both mission and margin.

It’s not just about digitizing documents.
Legal tech done right rethinks how legal work happens – and how it should.

As Yelena put it, “Legal tech is not just about digitizing documents. It’s about rethinking how legal work gets done.” That shift from filing cabinets to fully integrated workflows is where the real upside lies.

To listen or watch the full conversation, head over to YouTube. If you’re building in legal tech—or a complex, legacy-heavy vertical—Yelena wants to talk to you yesterday.

This article is for informational purposes only and does not constitute investment advice. Views expressed represent the opinions of the author and Jump Capital. Jump Capital may have investments in or pursue investments in the legal technology sectors discussed. References to specific approaches or technologies do not constitute investment recommendations.