Steve Singh
Steve Singh is Managing Director at Madrona. He is interim Chief Executive Officer at Spotnana. He was Chairman & CEO at Docker, Director at The Nature Conservancy, Director at Cornerstone OnDemand and Director at W Fund. He is Executive Chairman at Direct Travel, TROOP - Where do we meet? | Making Organizing a Meeting Easy for Anyone!, Magnify and CovenantIQ, and Board Member at Leaf Logistics and Clari.
Insurtech Faye raises $50M led by Madrona, bringing total funding to $100M as it scales AI and international growth
Faye, a Richmond-based travel insurance app, raised $50 million led by Madrona, bringing its total funding to $100 million since 2022 to scale AI, expand internationally, and improve claims and UX; the company reported millions of customers and $100 million in annualized revenue last year. Co-founder and CEO Elad Schaffer called the raise a shift from startup to scale-up as Faye pursues growth toward a possible future IPO.
Madrona Leads Faye’s Series C; Chris (Madrona) Joins Board as Faye Reimagines Travel Insurance
Madrona is leading Faye’s Series C investment because Faye has built a better, autonomous traveler care platform and improved whole-trip travel insurance that addresses slow, confusing incumbent products. The firm highlights travel’s growing disruptions and says Faye’s product delivers faster, more usable protection and better claims experiences for modern travelers.
Faye Raises $50M Series C on Aug 5, 2026 to Build Autonomous AI Traveler Care Platform, Total Funding Reaches $100M
Faye announced a $50 million Series C on Aug 5, 2026 to build an autonomous AI platform for traveler care, bringing total funding to $100 million and funding AI investments, partnerships, and global expansion.
By Steve
Troop Travel Founders on the Startup Journey and Relationships That Matter
Today, managing director Steve Singh sits down with Troop Travel Co-founders Dennis Vilovic and Leonard Cremer. Madrona invested in Troop and its corporate travel meeting management platform in 2021. These three talk about looking for the right problem to solve, to launch a company, and how you decide if it's the right time. They also discuss when you need to switch from bringing on generalists to bringing on experts, how to identify the right investors to work with, why working closely with customers and potential customers is so important, and so much more. So I'll go ahead and hand it…
Organizations
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Spotnana Chief Executive Officer [Interim] 2024–present, Executive Chairman 2020–present · current
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Direct Travel Executive Chairman 2024–present · current
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TROOP - Where do we meet? | Making Organizing a Meeting Easy for Anyone! Executive Chairman 2021–present · current
