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Climbing the Stack
Why human care still wins in an AI world
Matt Peters, CEO and Co-Founder of Fixify, joins Joey Pinz to explain why AI should help talented technicians do more meaningful work, not replace them.
Trust your gut: The leadership advice I'd give my younger self
Darragh Curran, CTO and Head of Engineering at Fin, explains why writing code has become the easy part of building software and why he hires for traits over experience.
MSPs are using AI. Stop hiding it.
Matt Tomlinson, Senior Director of MSP Partnerships at Fixify, joins WIN to explain why MSPs already running AI should stop hiding it and start selling the outcome.
Every AI agent is an identity: A CISO's security sequence
Kaarthick Subramanian, Chief Customer Officer and CISO at Atlas Systems, explains why AI projects fail on governance rather than model quality and how to translate technology risk into business risk for the board.
Why machines should stay in service of humans as AI goes always-on
Tope Iluyomade, former CIO and CISO and now Advisor at BetterUp, shares his "does the glass have a handle?" test for adopting new technology and how he learned finance as a fly on the wall in CFO meetings.
Engineer to C-suite: Why financial fluency and storytelling separate real executives
Matthew Sharp, CISO at Xactly and co-author of The CISO Evolution, shares how a sales job he once called the devil's work taught him how businesses run, and why moral authority beats formal authority.
A CEO sorted every employee into three AI buckets. Where would your team land?
Fred Bret-Mounet, VP of Security, Compliance and IT and CISO at Accela, explains why AI gives you six months to reinvent yourself and why everything internet-facing now needs auto-patching.
CIO vs. CISO: Resolving the ROI-versus-risk conflict when you hold both
Georgeo Pulikkathara, CIO and CISO at iMerit Technology, shares how he wins security budget by tying board asks to revenue deals, plus the PFC Romeo framework his team uses for every escalation.
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“Enabling chaos": how AppsFlyer hit 97% AI adoption across 1,300 employees
Chily Fachler, CIO at AppsFlyer, shares the "atoms" framework behind AppsFlyer's AI rollout and how his team got AI vendors to train the whole company.
"Someone who uses AI better than you will replace you": building fluency inside IT
Guillermo Porcaro, VP of IT Operations and Engineering at Medallia, shares how he restructured a global IT org without adding budget and why teams should only build AI they can troubleshoot node by node.
From bicycle sales to CIO: how a non-technical path accelerated leadership
Bryan Wise, CIO at 6sense, shares how he runs AI adoption through a champions program in every function and why he told his legal team to ignore every existing CLM vendor.
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From audit to Sr. VP of IT: The non-technical path to IT leadership
Stacey Moore, Sr. VP of IT at Flock Safety, explains why change management is 60% of any major IT deployment and how she brings directors into budget meetings to prepare them for VP.
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Career planning for CIOs: Define your last job first, then reverse-engineer the path
Rusty Atkinson, Head of Technology at Clearway Health and author of "The Integrity Edge," explains why the director promotion is where technical skills stop paying the bills and why boardrooms don't want to talk about technology.
The 90-day framework that moved IT from whack-a-mole to strategic execution
Kumud Kokal, CIO at Kiteworks, shares how mapping his team's view against his stakeholders' view exposed misaligned work, and how his team built three to four dozen AI agents.
Stop-start-continue: The one question that unlocks IT-business alignment
Bob Genchi, CIO/CISO at Scale Venture Partners, shares what a stalled outsourcing deal at Gap taught him about green metrics hiding unhappy users and how to debug organizational resistance like a technical problem.
Hire people smarter than you: The VP mindset shift
Noni Azhar, CIO at ProService Hawaii, explains why consulting advice gets questioned once it's free and how chess taught him to see problems from a stakeholder's side.
The morale fix most IT leaders miss: Why listening beats solving when teams struggle
Trevor Gregg, Professor at Columbia College, shares the SCARF method for stakeholder pitches and how he builds collaboration into his classroom labs.
The first 60 days: What new VPs actually do differently
Tom Quinn, VP and CISO at T. Rowe Price, explains why leaders who make VP refuse vague answers and how measuring one team's ticket volume uncovered a $50K-a-year automation win.
From director to CIO: What actually changes
Mark Settle, former CIO at Okta, explains why the move to CIO means working for every peer on the leadership team and how getting out into the business builds credibility.
Career jungle gym vs. career ladder: The path to IT leadership
Karl Mosgofian, former CIO at Gainsight, explains why good IT proposals still get rejected and how to reframe them as investments that win funding over everything else on the table.
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