Lanai —The Enterprise AI Interaction Observability Platform

Lanai envisions a future where enterprises can harness the transformative power of AI with full transparency, security, and control—eliminating the risks and fragmentation that hinder AI's potential today. We build foundational infrastructure that empowers organizations to convert isolated AI experiments into structured, secure, and scalable workflows that drive meaningful business impact.

Our technology pioneers real-time discovery and risk detection of AI interactions directly on enterprise devices, guarding sensitive data and regulatory compliance without sacrificing usability. By delivering unparalleled visibility and actionable insights, we enable teams to confidently unlock AI's promise while safeguarding privacy and trust.

As pioneers in AI observability and governance, we are crafting the essential operating system for the future of enterprise AI—balancing innovation with security to ensure AI becomes a reliable, integrated partner in every organization’s journey forward.

We've been tracking Lanai since they emerged from stealth mode, and honestly, they caught our attention for all the right reasons. Here's a company that's tackling one of the biggest headaches in enterprise AI: the fact that nobody really knows what's happening with AI tools across their organization.

Most companies we talk to have the same problem—employees are using ChatGPT, Claude, and dozens of other AI tools without IT knowing about it. Lanai's founders clearly felt this pain firsthand during their stints at Google, Meta, and VMware.

What Makes Them Different

Lanai's edge-based approach is genuinely clever. Instead of trying to monitor network traffic or maintain endless lists of AI tools, they run on-device models that actually see what prompts employees are typing in real-time. It's like having a security guard who can read over everyone's shoulder, but in a good way.

We were impressed that they achieved SOC 2 Type II compliance right out of the gate. That's not easy for a startup, but it shows they're serious about enterprise trust from day one.

The Leadership Edge

The founding team reads like a Silicon Valley all-star roster. Lexi Reese (former Gusto COO), Stephen Herrod (ex-VMware CTO), and Rajesh Raman (Google/Meta veteran) bring exactly the kind of enterprise platform experience you'd want for this challenge.

Having built massive infrastructure at companies like VMware and Splunk, they understand what it takes to sell into Fortune 1000 accounts. That's not something you can fake or learn quickly.

Real-World Impact

Here's what got our attention: Lanai already demonstrated $320K in saved costs for one client through risk mitigation. That's the kind of concrete ROI that makes CFOs pay attention, especially when AI budgets are under scrutiny.

Their "Datadog for AI workflows" positioning makes perfect sense to us. Every enterprise we know struggles with AI visibility, and Lanai seems to have cracked the technical challenge of discovery without being intrusive.

Who Should Care

If you're a CIO, CISO, or compliance officer at a large company, Lanai deserves a serious look. The $10+ million seed round from top-tier VCs suggests smart money believes in their approach.

We think they're well-positioned as AI regulations tighten and enterprises need better governance. Sometimes the best opportunities come from solving the un-sexy but critical infrastructure problems—and that's exactly what Lanai is doing.