21-year-old MIT dropouts raise $32M at $300M valuation led by Insight

Karun Kaushik and Selin Kocalar weren’t planning to raise a Series A so soon. Their AI compliance startup, Delve, which announced a $3 million seed round in January, was growing fast and signing customers at a steady clip.

Then, inbound interest started rolling in, COO Kocalar told TechCrunch.

Delve, which automates regulatory compliance with AI agents, ended up fielding multiple term sheets, eventually closing a $32 million Series A at a $300 million valuation. The round was led by Insight Partners, which took up most of the round, with participation from CISOs at Fortune 500 companies.

Insight has been “amazing to work with, and we felt they were the right long-term partner for us,” said the COO.

Delve’s new valuation represents a roughly 10x jump from its previous round. Similarly, its customer base has grown from the 100 companies it reported back in January to over 500, many of them fast-growing AI startups like recently minted AI unicorn Lovable, Bland and Wispr Flow.

And while the two-year-old company, made up of AI researchers from MIT, Stanford, and Berkeley, has seemingly struck gold by using AI to eliminate hundreds of hours of manual processes, its story began much differently.

Kaushik and Kocalar met as classmates during their freshman year at MIT. Both had deep interests in AI and health tech. Kaushik had already scaled a COVID diagnostic system to thousands of users during the pandemic. 

In 2023, they began working on an AI-powered medical scribe to help doctors handle patient documentation. However, handling sensitive healthcare information meant they quickly encountered the costly and time-consuming world of HIPAA compliance.

Instead of continuing with the medical scribe, they started building tools to help other companies get HIPAA compliant faster and more affordably. That pivot got the team into Y Combinator last year and helped them raise their seed round from General Catalyst, FundersClub, Soma Capital, and others. The founders dropped out during their sophomore year in 2023.

What started with HIPAA quickly expanded. “As our customer base grew, they started asking for support with other frameworks: SOC 2, PCI, GDPR, ISO, basically the whole alphabet soup of compliance,” Kocalar narrated.

Compliance paperwork can be necessary in everything from launching products to closing enterprise deals. But instead of driving growth, its manual work can become a bottleneck.

“Compliance frameworks are standardized. Businesses aren’t,” says CEO Kaushik. “That mismatch is why traditional software breaks down and teams fall back to duct-taped workflows across email, Slack, and shared drives.”

Delve replaces that busywork with AI agents that run in the background (after integrating with customers’ tools) like internal team members. These agents collect evidence, write reports, update audit logs, and track configuration changes across fragmented systems, automating compliance workflows in real time.

Kocalar says compliance is just the wedge into broader back-office operations. Long-term, the AI startup wants to automate a billion hours of other work — eventually expanding into adjacent areas like cybersecurity, risk, and internal governance.

Insight Partners’ interest reflects this roadmap.

“Since compliance touches every part of how a business runs, from scaling operations to closing deals to building customer trust, modernizing this function will modernize the entire organization,” said Praveen Akkiraju, managing director at Insight. “That’s what makes Delve’s approach so important.”

Still, the startup won’t be without competition. Several AI companies are emerging with agents to automate business workflows. In addition, larger AI labs like OpenAI are releasing general-purpose agents capable of performing complex tasks.

That said, Kocalar says these developments are a validation, not a threat, to Delve’s business. She points to the company’s domain depth in contrast to more general-purpose agents.

“We’re positioning ourselves to improve as AI advances and labs roll out more sophisticated agentic technologies. But what truly sets us apart is the deep, domain-specific knowledge we’re building into the platform,” she said. “Compliance is always shifting as new regulations emerge and existing ones evolve, with companies interpreting them in different ways. That’s where Delve stands out.”