After Earnings

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, joins01:06 Taking over as Twilio's CEO01:50 What Twilio does03:19 Fighting commoditization with pricing power and the CDP data asset05:20 Twilio's customer base07:29 Branded calls and fighting spam08:04 Building trust in the US telecom network11:21 WhatsApp, Meta, and other emerging messaging channels13:38 New products unveiled at Twilio's customer conference18:24 Personalizing the mortgage-shopping journey24:24 Q1 results 26:31 Capital allocation27:17 Outro and upcoming episodes

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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, Joins01:19 What Zscaler does: zero trust cybersecurity explained02:08 Castle and moat vs. doomsday bunker: the zero trust architecture04:34 Zscaler's customer base05:56 Project Glasswing: partnering with Anthropic on vulnerability research06:35 How frontier AI models find security vulnerabilities at machine speed09:03 Why Zscaler's stock is down 40% despite AI partnerships11:32 Ad break: KeyBank12:17 Using AI internally14:18 International expansion16:46 M&A strategy18:42 Acquisition multiples and the AI premium19:27 How Zscaler evaluates ROI on acquisitions20:45 Earnings results22:50 The war for enterprise sales talent24:36 Capital allocation25:25 Outro and upcoming episodes

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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, Joins00:38 Q1 earnings highlights: revenue, EBITDA, and profitability01:25 Prediction markets: threat or opportunity?02:53 Cannibalization concern: what the data actually shows03:34 Why sportsbook users aren't switching to prediction markets05:26 Prediction market regulation: CFTC rulemaking and legislative bans06:38 Market integrity: fighting insider trading and gaming the system07:58 The Super App: from seven apps to one unified platform09:33 Super App expansion: lotteries, horse racing, and what's next10:06 Could DraftKings move into stock trading?11:08 Rail Bird acquisition: building a prediction market exchange12:07 Ad break: KeyBank12:38 ESPN, NBC, and Amazon: the content partnership strategy14:19 What exclusive broadcast deals actually do for the bottom line15:06 League partnerships vs. broadcast deals: a disciplined approach16:14 State tax hikes: the regulatory landscape17:21 Black market competition: offshore sportsbooks and the tax disadvantage19:26 Cost-cutting and margin defense20:07 Path to 30% EBITDA margins21:26 Breaking down the balance sheet22:23 Prediction markets as a billion-dollar TAM opportunity22:43 Outro and upcoming episodes

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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, Joins01:47 Go big or go home: the strategy shift explained03:32 The cost of not swinging for a billion users04:05 Analyst skepticism addressed05:36 Shots on goal: product, Asia, and performance marketing07:28 Speaking features, AI ingredients, and learning outcomes08:00 Chess, math, and music as new growth vectors10:03 Asian language learners and China's English boom11:34 AI-powered content creation13:51 Where AI costs show up on the P&L14:42 Gross margin compression and investment guidance15:05 2026 guidance: bookings, revenue, and EBITDA targets16:18 The balance sheet: $1B+ cash and buyback strategy18:01 M&A appetite: tuck-ins vs. transformational deals19:34 Why Duolingo is staying software-focused20:43 Gillian's transition from board member to CFOAfter Earnings is brought to you by Stakeholder Labs and Morning Brew.For more go to https://www.afterearnings.comFollow UsX: https://twitter.com/AfterEarningsTikTok: https://www.tiktok.com/@AfterEarningsInstagram: https://www.instagram.com/afterearnings_/Reach OutEmail: afterearnings@morningbrew.com$DUOL
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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 positioning Booking for long‑term growth.After Earnings is brought to you by Stakeholder Labs and Morning Brew.For more go to https://www.afterearnings.comFollow UsX: https://twitter.com/AfterEarningsTikTok: https://www.tiktok.com/@AfterEarningsInstagram: https://www.instagram.com/afterearnings_/Reach OutEmail: afterearnings@morningbrew.com$BKNG
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