Lanai Software is an AI observability platform that helps enterprises detect hidden AI use and recommend which AI tools will benefit them in cost savings. Pulse 2.0 interviewed Lanai Software co-founder and CEO Lexi Reese to gain a deeper understanding of the company.
Lexi Reese’s Background
Could you tell me more about your background? Reese said:
“I’ve built infrastructure through every major tech shift for 30 years—internet, mobile, cloud, now AI. At Google, I ran the ML ads platform handling billions of daily AI decisions. At Gusto, I scaled the payroll and compliance company as COO. Here’s what’s different about AI: enterprises are spending $500-2,000 per employee on AI tools,the biggest tech spending spree since cloud adoption while being completely blind to what’s actually happening. Our data shows 89% of AI usage is invisible to IT teams. That’s a $120 billion blind spot.”
Formation Of The Company
How did the idea for the company come together? Reese shared:
“We kept hearing the same story from every CISO and CIO: ‘My people are using AI everywhere, and I’m flying completely blind.” One guy told me, “I can see them going to ChatGPT.com, but I have no clue if they’re leaking our IP or just asking for grammar help.’”
“It’s not just ChatGPT, it’s Cursor for coding, AI in SaaS apps like Salesforce and Notion. Traditional security tools see web traffic, not actual prompts where the real risk – and opportunity – lives.”
“Steve Herrod, VMware’s former CTO, immediately got the structural problem: ‘It’s like managing cloud infrastructure without seeing inside the virtual machines.’”
“That’s when we realized prompt-level visibility isn’t just a product, it’s foundational infrastructure for the AI era.”
Favorite Memory
What has been your favorite memory working for the company so far? Reese reflected:
“A Fortune 500 customer discovered they had 34 AI tools running when they thought they had 5. But instead of panicking, they used our visibility to scale what worked and secure what didn’t. We helped them cut AI subscriptions from 23 to 8 high-impact tools while increasing productive AI usage by 300%. Watching leadership turn AI chaos into AI strategy—that’s why we exist.”
Core Products
What are the company’s core products and features? Reese explained:
“Lanai runs lightweight AI detection models directly on employee devices—no cloud routing, no infrastructure changes, 24-hour deployment via existing MDM systems. We provide dynamic detection of any AI interaction, real-time prompt analysis for sensitive data exposure, and complete data sovereignty. Think edge-based observability for AI conversations. It’s the first platform built for prompt-level visibility instead of just tracking URLs.”
Challenges Faced
Have you faced any challenges in your sector recently? Reese acknowledged:
“The biggest challenge is that AI adoption is completely organic—employees are upgrading personal ChatGPT accounts, using coding agents like Cursor and Windsurf, and every SaaS vendor is embedding AI without asking. Traditional security approaches can’t handle this dynamic, conversational technology. Our breakthrough was moving AI observability from the network to the edge—analyzing prompts on-device instead of routing everything through centralized systems.”
Evolution Of The Company’s Technology
How has the company’s technology evolved since launching? Reese noted:
“We started with detection and what AI tools are people using? But the real breakthrough was our edge-based approach. Instead of trying to route sensitive conversations through cloud systems, we run AI models directly on devices. This gives us prompt-level visibility while maintaining complete data sovereignty. Now we’re expanding toward agent-to-agent monitoring as autonomous AI systems become reality.”
Significant Milestones
What have been some of the company’s most significant milestones? Reese cited:
“We’re deployed at Fortune 500 companies and have raised $11.5M, including a recent extension from Benchstrength VC. We’ve achieved SOC 2 Type II compliance and are scaling one healthcare customer from pilot to 20,000 employees. Most importantly, we’re proving that AI observability isn’t just about security—it’s about ROI optimization.”
Customer Success Stories
When asking Reese about customer success stories, she highlighted:
“A financial services client found engineers using 12 different coding agents, essentially giving their platform architecture to third parties. We helped them secure approved AI tools while eliminating $700K in AI tool waste—they had 23 subscriptions but 65% of licenses were unused. Meanwhile, we scaled their most valuable AI workflows across departments, increasing productivity while protecting their competitive advantages.”
Differentiation From The Competition
What differentiates the company from its competition? Reese affirmed:
“Everyone else is trying to manage AI with static ‘approved lists’ or cloud-based DLP that can’t see actual prompt content. We run AI models on devices, giving us dynamic detection across any AI application without routing data externally. Traditional tools see the network traffic—we see the prompts and responses where real risks and value live.”
Future Company Goals
What are some of the company’s future goals? Reese emphasized:
“We’re expanding from human-AI observability toward agent-to-agent coordination as autonomous AI systems execute workflows independently. Our edge architecture is built for this future—providing the foundational intelligence layer for enterprise AI transformation, whether it’s humans prompting AI or agents coordinating with other agents.”
Additional Thoughts
Any other topics you would like to discuss? Reese concluded:
“The window for getting ahead of AI visibility is closing fast. Every day, more employees sign up for personal AI accounts, more SaaS vendors embed AI features, and more coding agents get access to proprietary systems. By the time companies realize the scope of their AI exposure, their competitive advantages may already be in someone else’s training data. The future belongs to companies that see clearly and act decisively.”
