Ann Berry is joined by Ariel Cohen, Co-Founder and CEO of Navan, to discuss how the company is modernizing business travel, leveraging AI to improve the traveler experience, and pursuing acquisitions to support its global expansion. 00:00 Ariel Cohen, CEO and Co-Founder of Navan, joins 01:25 What Navan does: corporate travel and expense management explained 02:51 Inside the Navan app 05:10 Navan's customer base 06:07 Who Navan sells to 07:52 Legacy travel software 09:03 Why AI companies still ne

Ann Berry is joined by Khozema Shipchandler, CEO of Twilio, to discuss the company's turnaround strategy, the changing landscape of customer communication and how Twilio is leveraging AI to personalize interactions. 00:00 Khozema Shipchandler, CEO of Twilio, joins 01:06 Taking over as Twilio's CEO 01:50 What Twilio does 03:19 Fighting commoditization with pricing power and the CDP data asset 05:20 Twilio's customer base 07:29 Branded calls and fighting spam 08:04 Building trust in the US teleco

Ann Berry is joined by Kevin Rubin, CFO of Zscaler, to discuss how the company's zero trust model protects nearly half of the Fortune 500, what frontier AI models revealed about cybersecurity vulnerabilities and whether the software selloff is missing the bigger picture. 00:00 Kevin Rubin, CFO of Zscaler, Joins 01:19 What Zscaler does: zero trust cybersecurity explained 02:08 Castle and moat vs. doomsday bunker: the zero trust architecture 04:34 Zscaler's customer base 05:56 Project Glasswing:

Ann Berry is joined by Alan Ellingson, CFO of DraftKings, to discuss how the company is navigating the rising popularity of prediction markets, its new “Super App” designed to let users seamlessly operate across jurisdictions, and how DraftKings is working to maintain integrity in sports betting. 00:00 Alan Ellingson, CFO of DraftKings, Joins 00:38 Q1 earnings highlights: revenue, EBITDA, and profitability 01:25 Prediction markets: threat or opportunity? 02:53 Cannibalization concern: what the

Ann Berry is joined by Gillian Munson, CFO of Duolingo to discuss the company's transformation as it pursues user growth over short-term revenue. They dive into Duolingo’s expansion beyond language learning, growth opportunities across Asia, and how AI is accelerating content production. Gillian also reflects on transitioning from Duolingo’s board to stepping into the CFO role. 00:00 Gillian Munson, CFO of Duolingo, Joins 01:47 Go big or go home: the strategy shift explained 03:32 The cost of no

Ann Berry is joined by Glenn Fogel, CEO of Booking Holdings, to survey the state of the global travel industry amid geopolitical uncertainty and Glenn’s strategy to creating synergy across multiple brands — including its Connected Trip vision. They unpack the rise of alternative accommodations versus Airbnb, and the role of AI through products like Priceline’s Penny and new startup initiatives. Glenn also shares how he thinks about attracting entrepreneurial talent, navigating M&A and positionin