This is a conversation about what happens when AI screens resumes before a human ever sees them, why “AI integration specialist” means something different to everyone who says it, and the case for staying a generalist in a market that keeps chasing the next niche.
We also get into the quiet cost of the specialist bet, how fast a hot skill set can turn cold, and why the people who keep their base skills sharp are the ones still standing when the trend moves on.
Jack Smith started his career installing Windows 95 as a HelpDesk Tech and has spent the years since moving data centers, opening data centers, and learning over and over that the skills worth keeping aren’t the ones tied to a single tool or title.
Now, as AI reshapes hiring on both sides of the table, he’s watching the same mistake repeat itself: companies rolling three jobs into one impossible profile, and candidates rewriting themselves into keyword matches for roles they’ve never actually done.
Bonus: what 25 years of hard-won IT stories taught Jack about learning from failure instead of hiding it — the same instinct that led him to launch his own podcast.
About Jack Smith
Jack Smith is an Infrastructure Project Manager and the host of IT Horror Stories with Jack Smith, a podcast exploring the human side of technology. He spent more than two decades building a career across cybersecurity, data centers, networking, and digital transformation, learning that resilience comes from what you take from failure, not from avoiding it. Outside of infrastructure work, he’s been part of the demo scene — real-time digital computer art on old and new hardware — since 1991.
Connect with Jack: ithorrorstories.eu | LinkedIn | Spotify | Apple | YouTube
About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.
Connect with Christine: bio.site/dreamsanddelivery | LinkedIn
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