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Be Fearless Podcast by SquareX

Why Business-Aligned Security Wins | Coleen Coolidge, ex-CISO Segment and Twilio, Startup Advisor

22 Aug 2025

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Coleen Coolidge, ex-CISO of Segment and Twilio and startup advisor, didn't start in cybersecurity - she was a new project manager who got thrown into the deep end, but that discomfort launched an 18-year career that would see her build security teams from scratch at companies like Segment and Twilio. Now advising early-stage startups, Coleen shares insights about why security teams fail, how to actually talk to executives about risk, and why most founders are solving the wrong problems.0:00 Coleen’s cybersecurity origin story5:40 Transforming security chaos into a reusable security blueprint19:27 Pull in key business leaders to endorse your plan22:56 Convert your security gaps and desired outcomes into vendor requirements25:54 Where to start if you want a risk-based journey31:49 The dangerous allure of “shiny new things” in security45:36 Why you need to stay open and curious in security🔔 Follow Coleen and Aleksandra on:https://www.linkedin.com/in/ecoleenc/https://www.linkedin.com/in/aleksandra-melnikova-1012/🔥 Powered by SquareXDeployed as a lightweight extension, SquareX turns any browser, on any device, into a secure enterprise browser. Find out more about SquareX at https://hubs.la/Q03rPcbf0

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