Climbing the Stack

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 structured L&D program that trained 250 employees across departments as AI builders in year one. The result: 97% daily adoption with employees using AI multiple times a day.

Chily walks Matt through the other half: a top-down framework called "atoms" where each department identified its three or four core activities, selected half, and built AI use cases against them. The biggest win was a Know Your Customer skill built on Claude and MCP that now prepares 300-400 go-to-market employees before every customer meeting. He's also direct about the atoms that never took off, why he thinks measurement is still the hardest problem in enterprise AI, and how a CIO career built through business analysis rather than engineering shaped his approach to leading people who are more technical than him. His leadership playbook runs on Lencioni's Five Dysfunctions of a Team, and he tests it with one question: when someone asks what your team is, do you name your function or your leadership team?

Topics discussed:

• Two-tier AI strategy: "enabling chaos" paired with top-down "atoms"

• Hitting 97% daily AI adoption by welcoming personal use as the on-ramp

• IT and L&D partnership to train 250 AI builders across departments

• Company-wide KYC skill built on Claude and MCP for go-to-market prep

• Vendor-funded AI training through strategic licensing negotiations

• Why AI's democratized nature requires transformation from within, not IT-led

• Building a CIO career through business analysis, not engineering

• Testing leadership health with Lencioni's "what is your team?" question

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 talent.

In this episode, Guillermo talks with Matt about the business case he built to make that reorg happen, the line he draws between using AI to build something and actually understanding what you built, and why he thinks the IT frontline is about to look completely different.

Topics Discussed:

• Taking a deliberate step down in title to gain access to a higher-trajectory environment

• Self-funding a reorg by reallocating APAC contractor spend toward LATAM FTEs for time zone and cost alignment

• Teaching ICs to trace how their individual deliverables create failure points up the chain

• Applying an engineering mindset to org design: mapping teams as components in a system

• The "build vs. understand" problem when AI generates code your team can't support or troubleshoot

• Node-based agentic workflows as a more supportable alternative to black-box AI builds

• Giving every team member a safe, contained AI environment to experiment and build as a skill

• Why the AI skill gap will be filled by peers, not leadership, if you wait too long to start

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 actually doing inside 6sense to prepare his workforce for a future where the work itself is being redefined.

Bryan also breaks down his approach to enterprise AI adoption, from how he's structuring AI champions groups with skin in the game, to why he challenged his legal team to completely reimagine contract lifecycle management instead of buying the same tools everyone else buys. If you want a ground-level view of what a forward-thinking CIO is doing right now, this one is worth your time.

Topics discussed:

• Why a sales background accelerates the climb to CIO

• Speaking in business outcomes as a non-negotiable career skill

• The CIO as connective tissue across all business functions

• AI champions groups with accountability, gamification, and prizes

• Mandatory AI training and redefining what a modern worker looks like

• Reimagining CLM from scratch instead of buying legacy solutions

• Why brownfield environments require a North Star, not a wholesale swap

• Peer networks as the most reliable signal in a noisy information environment

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 this episode, she gets specific about what actually changes when you cross into VP-level leadership, how she coaches directors into that seat, and why she thinks change management is 60% of the real work on any major deployment, yet still the most misunderstood part of the job.

She also breaks down her stakeholder mapping approach, the questions she uses in 1:1s to surface upstream problems that teams don't even know they're causing, and the scenario she forces on every team member: if we're a billion-dollar company tomorrow, what breaks with your current setup?

• 60/40 split: why change management outweighs technical work

• Using org charts to diagnose organizational dysfunction early

• Devil's advocate questioning to expose upstream root causes

• Pulling directors into budget conversations as a development tool

• The billion-dollar scalability scenario as a forcing function

• Building trust through small wins before tackling complex problems

Topics discussed:Re-reading The New Automation Mindset in 2025 and what's different now

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 framework for climbing to the C-suite. His approach centers on what he calls the "integrity edge" - the measurable engagement, loyalty, and innovation you earn when teams know they're protected and trusted. But getting there required learning that boardrooms don't care about technology, that your VP boss might steal your ideas, and that the firmware upgrade that bricked production was ultimately your failure, not the engineer's who forgot to check the backup.

Topics discussed:

• Defining the "integrity edge" as measurable team outcomes from trust-based leadership

• Why the director promotion is the hardest transition where technical skills stop mattering

• Translating C-suite peer objectives into technology actions rather than pitching solutions

• Embedding in operational contexts like sales calls to identify friction points before they're articulated

• Applying extreme ownership where backup verification failures roll up to leadership, not just the engineer

• Starting career planning with your final role and reverse-engineering required capabilities

• Coaching through personal "why" discovery to convert disconnected actions into character-driven decisions

• Treating AI like cloud in 2008: transformative potential undermined by solution-first thinking

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 for career decisions remains consistent: evaluate opportunities through the lens of "how hard can this be?" At FBN, that question led him to dairy farms in Minnesota, watching a fifth-generation farmer track 400 head of cattle producing 29,000 gallons of milk daily by sight alone. The experience taught him that agriculture wasn't a business to customers; it was identity. That perspective shift defines his approach to IT leadership.

Topics discussed:

• Structuring a personal board of directors with domain-specific advisors for compensation strategy, technical architecture, and industry navigation

• Running the "inside out and outside in" assessment framework in the first 90 days to surface misalignment between internal team perspective and stakeholder reality

• Defining IT's mission, vision, and strategy as organizational constitution, moving teams from reactive "whack-a-mole" mode to strategic alignment

• Building the "Stevenson family" of AI agents with distinct roles (Caroline for HR/IT, Natalie for product support) using Microsoft Teams integration and connected infrastructure systems

• Navigating the VP-to-CIO transition by learning to speak peer language across finance, legal, and business unit leadership

• Applying Intuit's "follow me home" observation methodology, catching critical UX patterns like extension fields in phone numbers that UAT testing missed

• Establishing shared-responsibility AI development model where business units propose solutions and IT provides funding and technical enablement

• Reframing technology decisions as a three-way evaluation: human execution, traditional automation, or agent deployment

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 portfolio companies on scaling IT operations while bringing that hard-won perspective on what actually works versus what looks good in a business case.

Topics discussed:

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 leaders who scale from those who stall.

Topics discussed:

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 and skip-levels couldn't touch. His team needed to feel heard before they could move forward. The insight applies directly to IT leadership: when morale craters, your instinct to problem-solve actively prevents recovery. Your team already knows the technical fixes. They need you to facilitate the conversation, not dominate it.

Trevor applies this same principle teaching students ranging from concurrent high school enrollment to career-switchers in their 50s. His pre-apprenticeship lab strips away the illusion that IT careers are built on technical prowess alone. Students construct the entire infrastructure from raw cable and blank machines. When one team's DHCP configuration blocks another's progress, collaboration isn't optional—it's survival. He's deliberately architected this interdependency because the failure mode for technical people isn't debugging, it's asking for help.

The SCARF framework he teaches addresses the stakeholder problem most IT leaders learn through painful failure: your architecture dies if your audience's threat response activates during the pitch. Status, Certainty, Autonomy, Relatedness, Fairness—these aren't soft skills. They're the variables that determine whether your proposal gets funded or archived. Trevor trains students to structure conversations that bypass defensive reactions, a skill most Directors only master after years of rejected proposals.

His non-traditional path—astronomy degree, NASA Kepler telescope research, family pizza business, bipolar diagnosis—built leadership instincts that traditional IT career paths don't develop. Learning Linux through astronomy research created deeper technical foundations than boot camps provide. Managing pizza shop crews taught him servant leadership before he knew the term existed. Completing his degree while managing mental health struggles taught him that accomplishment becomes addictive once you prove you can summit something that looked impossible.

Topics discussed:

"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 hours per week.

Quinn's measurement-first approach at T. Rowe Price proves you can't automate what you don't measure, but more importantly, the act of measuring itself becomes the first automation win. His team didn't start with the perfect metric—they started with any metric they could get their hands on, then systematically reduced the friction of collecting it. That cultural shift from "we handle a lot" to "here's the exact number and where it comes from" created the foundation for every operational improvement that followed.

The conversation also covers Quinn's listening tour methodology for new leadership roles, where asking "if there's anything at all that isn't working — doesn't have to involve my team — I want to know" surfaces the budget constraints and cross-functional friction that shape what's actually achievable. His reference points range from Navy close-quarter operations to early NASA's learning culture to Kimberly Clark's decision to sell their Wisconsin mills and pivot from low-margin cardboard to high-margin paper products.

Topics discussed: