Climbing the Stack

When Georgeo X. Pulikkathara joined iMerit Technology as CISO, the role came with infrastructure responsibility attached. His solution was to take the CIO title too and fund security controls directly from that budget. It's a structure he'd spent years viewing as a conflict of interest (CIO manages toward ROI, CISO manages toward risk), and this episode is his case for when it works. He al...

Most enterprise AI rollouts start with a pilot team, a controlled use case, and a measurement framework. Chily Fachler, CIO at AppsFlyer, started by giving all 1,300 employees AI tools and telling them to build whatever they wanted, with no required use cases and no productivity tracking. He calls this half of the strategy "enabling chaos," paired with CEO-level sponsorship and a structu...

Guillermo Porcaro took a deliberate step down to join Medallia as the IT guy for the Argentina office, even after having already built and managed teams. He saw something in the culture worth betting on, and that read paid off. He's now Vice President, IT Operations and Engineering at Medallia, having designed and executed a self-funded reorg that restructured global delivery around LATAM tale...

Bryan Wise didn't start in IT. He started selling bicycles. After self-studying for his MCSEs in three months and bluffing his way into his first technical role, he's spent 30 years building through the ranks at companies like DocuSign, Snowflake, GitLab, and now 6sense as CIO. This episode covers how a sales-first mindset became a career accelerator in the C-suite, and what Bryan is actua...

Stacey Moore's path to Sr. VP of IT ran through Big Six audit, an MBA, seven years of management consulting, and five consecutive high-growth startups. That's not a typical IT career trajectory, and it shows in how she leads. Most IT leaders learn business acumen on the job, usually after they've already hit a ceiling. Stacey built it first, then applied it to technology leadership. In...

The director-to-VP jump breaks most technology leaders. Rusty Atkinson saw it coming. After realizing he was an above-average engineer but never the head geek in the room, he made a calculated bet: leadership ability would take him further than technical depth. Twenty years later, as VP of Technology at Clearway Health and author of "The Integrity Edge," he's built a repeatable frame...

Kumud Kokal's career path defied his CPA father's expectations, pivoting from accounting to software engineering during the Internet's early days. Over 25 years, he built technical fluency across wildly different business models, from Intuit's consumer finance to Airbnb's hospitality platform to FBN's agriculture technology, before landing as CIO at Kiteworks. His framework...

Bob Genchi's seven years at Gap Inc. became his "postgraduate education" in IT. He watched a major IBM outsourcing initiative that initially promised efficiency turn into a morale-destroying productivity sink. The experience taught him to prioritize what traditional metrics miss entirely: user sentiment and organizational trust. Now as CIO/CISO at Scale Venture Partners, he advises early-stage por...

Noni Azhar turned a consulting career into C-suite leadership by mastering what most IT leaders miss: the skill of making stakeholders believe your solution was their idea. As CIO at ProService Hawaii , he shares the frameworks that carried him from technical consulting through each inflection point—IC to manager, director to VP, VP to CIO—and why self-compassion during those transitions separates...

Trevor Gregg supervises county IT operations and runs Columbia College's Google-funded IT pre-apprenticeship program. When he inherited a service desk with morale in the basement, he did something most IT leaders never consider: he brought a county board supervisor directly to his team—not to announce fixes, but to listen without offering solutions. That single move solved what performance reviews...

"How many IAM tickets do you close a day?" When Tom Quinn asked his team, the answer was "a lot." That non-answer cost them six hours just to compile basic metrics. Two weeks later: four hours. Two more weeks: one hour. Then real-time. That progression unlocked the insight that 80% of tickets came from one call center with high turnover — leading to automated role-based provisioning that saved 20...

Most IT leaders spend their first week as CIO in meet-and-greets. Mark Settle spent his time sitting in quarterly sales reviews in Minneapolis—where executives looked at him confused, asking why he'd want to be there. That confusion was the point. He was building field credibility that would matter when things got hard. The VP-to-CIO transition isn't what people expect. As a VP, your CIO shields y...

Most directors think the CIO job is about making bigger technical decisions. Karl Mosgofian discovered it's about learning an entirely different language: investment language. When your "perfect" solution reaches the CEO, they're choosing between 30 competing priorities and can fund maybe 6. His brutal mentor with the red pen taught him the empathy framework: if you can't see your presentation thr...