Startup Speed vs Enterprise Scale: What Actually Works? | CTO ⁨@CDW⁩

Phil Taylor, CTO ⁨@CDW⁩ , built a 250-person services company from the ground up, sold it to CDW, and now runs their Digital Velocity business unit. But what makes his story compelling isn't the exit — it's how he got there.At 21, he was distributing half a billion dollars in checks. One error could've bankrupted the company. Years later, he learned the hard way that being right matters less than helping your team win. He'll tell you about the Silverlight bet that taught him to ship imperfect products fast, the founders he picked wrong, and why his best business came from investing in people he let go.He's also refreshingly honest about AI hype, why most services companies miss the obvious, and how to actually scale when you can't touch the code your teams are shipping.If you're building a company, leading engineers, or trying to figure out how to compete without a shiny product, this one's worth your time.________________________________________________Timestamps00:00 Meet Phil — from software engineer to CTO at CDW01:51 The builder mindset, started at age 1302:30 Distributing $500M in checks at 2104:38 The team rebellion that humbled him as a leader05:37 Choosing to win with your team, not be right06:56 Ship value fast — perfect is the enemy of good07:19 Listen to customers, don't sell them09:09 The honest manager who told him to go start something10:11 Building serverless before AWS Lambda11:06 Pivoting to services, betting on Kubernetes12:44 Exiting to CDW during the pandemic13:28 Investing in people — your best network effect15:32 The jump to enterprise — processes and structure18:40 Running services like a product with real standards19:08 AI quality control — why manual testing still matters21:18 Staying on top of innovation24:13 Zero to one in consulting — partnerships first26:04 Building your portfolio of capabilities28:40 AI is overhyped, cloud is a journey ________________________________________________🔗 Connect with Phil Taylor → https://www.linkedin.com/in/ptaylor1/🔗 Connect with Mala Ramakrishnan → https://www.linkedin.com/in/malaramakrishnan🎧 Subscribe to the podcastYoutube: https://www.youtube.com/channel/UCnL3D6aI60R-cCvypFIkh4ASpotify: https://open.spotify.com/show/1NIDE4cT5fuVjC3HaGbCDK?si=eoSTNmhqQNKHQl9d1Jx0UQApple Podcast: https://podcastsconnect.apple.com/my-podcasts/show/talking-to-the-leaders-of-ai-the-ceo-series-with-mala/22ad2bae-502b-4eb1-aa74-53bc79754db7Visit our Website: https://malaramakrishnan.com | https://founderscreative.org