Climbing the Stack

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How do you go from Director to CIO? Host Matt Peters, CEO of Fixify, sits down with IT executives who've made the climb to unpack the pivotal decisions, career-defining moments, and hard-won lessons that got them there. If you're a VP or Director of IT looking for practical advice to reach the C-suite, this is the podcast that finally focuses on your journey—not just the latest tech trends. Real stories. Real strategies. Real career growth.

Episodes

  1. From audit to Sr. VP of IT: the non-technical path to IT leadership | Stacey Moore

    MAR 3

    From audit to Sr. VP of IT: the non-technical path to IT leadership | Stacey Moore

    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

    36 min
  2. Career planning for CIOs: Define your last job first, then reverse-engineer the path | Rusty Atkinson

    FEB 17

    Career planning for CIOs: Define your last job first, then reverse-engineer the path | Rusty Atkinson

    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

    40 min

  3. FEB 3

    The 90-day framework that moved IT from whack-a-mole to strategic execution | Kumud Kokal

    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

    36 min
  4. Stop-start-continue: The one question that unlocks IT-business alignment | Bob Genchi

    JAN 20

    Stop-start-continue: The one question that unlocks IT-business alignment | Bob Genchi

    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: Gap Inc.'s IBM outsourcing as a cautionary tale in prioritizing cost reduction over organizational health The "assume user" debugging technique applied to organizational resistance and politics Operating modality and speed versus org size as the real determinant of IT structure Treating each business unit head as a direct report with quarterly stop-start-continue conversations Using "what do you wish IT would start, stop, and continue doing" as your primary discovery question Why search improvements matter more than AI agent hype for near-term IT operations value Distinguishing genuine AI advancement from rebranded trigger jobs and workflow automation Building IT value chain visibility from top-of-funnel through revenue recognition The shift from entry-level IT hiring freezes based on premature AI replacement assumptions Ken Blanchard's situational leadership framework as essential reading for IT managers EFF's privacy-focused podcast as professional development for security-minded IT leaders

    38 min
  5. Hire people smarter than you: The VP mindset shift | Noni Azhar

    JAN 7

    Hire people smarter than you: The VP mindset shift | Noni Azhar

    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: The consulting-to-internal IT transition and why being "right for free" requires different influence tactics than charging for expertise Chess-board thinking for stakeholder management: seeing problems from the other side to understand what they're not saying Career inflection points from IC through CIO and managing the tug-of-war between staying technical and building strategic vision The "let go or get left behind" moment when you stop being the subject matter expert and start hiring people smarter than you Building team cultures around directness and transparency where people aren't walking on eggshells about mistakes Making unique mistakes as a forcing function for team learning rather than repeating the same failures AI as augmentation versus automation and why the destination feels less clear than cloud or digital transformation ever did How entry-level skill requirements shifted and why new hires need different capabilities than previous generations Finding mentors who've climbed the ladder you want to climb and building peer networks for practical versus theoretical knowledge The people-process-technology triangle as a north star for solving problems that span organizational boundaries

    28 min
  6. The morale fix most IT leaders miss: Why listening beats solving when teams struggle | Trevor Gregg

    12/16/2025

    The morale fix most IT leaders miss: Why listening beats solving when teams struggle | Trevor Gregg

    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: Solving morale crises by facilitating listening sessions with leadership instead of proposing solutions Using the SCARF method to structure stakeholder conversations that prevent defensive threat responses Building problem-solving capacity by designing labs where infrastructure failure is required Creating forced collaboration through shared dependencies like DHCP and network configurations Developing servant leadership credibility by running cable day two after arriving in a suit day one Learning Linux through NASA telescope work and why non-traditional paths build unexpected technical depth Teaching customer service through role-play when students would rather avoid human interaction entirely Why bipolar diagnosis and degree completion struggle created addiction to accomplishment

    36 min
  7. The First 60 Days: What New VPs Actually Do Differently | Tom Quinn

    12/02/2025

    The First 60 Days: What New VPs Actually Do Differently | Tom Quinn

    "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: The six-hour to real-time measurement progression that revealed 80% of IAM tickets came from one call center Why starting with coarse-grained metrics beats waiting for perfect data architecture Building measurement culture by making data collection progressively easier, not by mandate The listening tour question that surfaces constraints stakeholders won't mention in first meetings Cross-referencing feedback across teams to decode what people mean versus what they say Creating psychological safety by stating failure plainly: "that didn't work, and there are implications" Early NASA's learning culture versus Space Shuttle's career-risk avoidance that killed dissent Applying the Kimberly Clark "sell the mills" framework to legacy portfolio decisions How a political science degree and oil politics coursework paid off decades later in finance Why AI hits bumpy roads in organizations practicing optics over actual data-led insights

    56 min
  8. From Director to CIO: What Actually Changes | Mark Settle

    11/18/2025

    From Director to CIO: What Actually Changes | Mark Settle

    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 you from unhappy business partners—even if people complain about your data warehouse, the CIO knows nobody could run it better. As CIO, that protection disappears. You can't succeed unless all your peers are happy because the CEO and CFO constantly poll them for feedback on your performance. Company politics shifts from occasional management to your daily job. Mark's credibility playbook centers on three moves: physically embedding in business operations (warehouse tours, field QSRs), identifying the one or two perception-shaping lieutenants in each department who influence their executive's view of IT, and recognizing that executives judge your seriousness by whether you show up—even when you learn nothing new. The tactic sounds soft until you realize these lieutenants shape whether your projects get funded. What we cover: Losing hierarchical protection at C-level where the CIO no longer shields you from business partner complaints Building executive credibility by attending operational reviews where business leaders initially question why you're there Identifying perception-shaping lieutenants in each department who influence C-level executives' views of IT Avoiding the super user trap where IT builds edge-case customizations that average employees never use Meeting all executives during the interview process to create subliminal buy-in before day one Preventing your own IT team from poisoning your perspective on business partners through constant complaints Distinguishing AI's potential from automation ROI through bandwidth and information timing constraints that have always limited business processes Redesigning service desks from reactive ticket systems to proactive productivity loss prevention Justifying productivity investments using security's playbook for risk-based tool decisions Serving as gotcha consultant rather than policeman when business partners evaluate AI tools Rejecting the entry-level job death narrative by recognizing continuous role evolution with each technology wave Managing agent networks using API management principles around clumping versus splitting functionality

    43 min
  9. Career Jungle Gym Vs Career Ladder: Karl Mosgofian's Path To IT Leadership

    11/04/2025

    Career Jungle Gym Vs Career Ladder: Karl Mosgofian's Path To IT Leadership

    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 through the CEO's eyes, you're dead in the water. Karl's journey from programmer to CIO at Gainsight spanned over three decades in IT leadership, transforming IT from support function into growth catalyst. His networking evolution went from awkward forced lunches to essential peer relationships he can't do the job without. He built deep business fluency without an MBA by applying technical curiosity to business domains. What we cover: Reframing IT asks as investment decisions, not technical ones, to speak the CEO's language Why CIOs develop 360-degree business views that most executives lack — touching every part of quote-to-cash Applying technical curiosity to business domains to build fluency without formal training Building your peer network proactively before you're senior enough for vendor-hosted CIO dinners How SaaS moved IT from application owner to integration and governance coordinator AI following democratization patterns: more distributed capability requires stronger central coordination The 20 "amount" fields problem in Salesforce—why semantic clarity makes or breaks enterprise data Mapping semantic layers from business-critical analytics backwards, avoiding low-level field noise Career jungle gym philosophy: trying adjacent roles temporarily to build cross-functional depth Learning CEO perspective to understand why good ideas don't get funded

    32 min
  • 9 Episodes

About

How do you go from Director to CIO? Host Matt Peters, CEO of Fixify, sits down with IT executives who've made the climb to unpack the pivotal decisions, career-defining moments, and hard-won lessons that got them there. If you're a VP or Director of IT looking for practical advice to reach the C-suite, this is the podcast that finally focuses on your journey—not just the latest tech trends. Real stories. Real strategies. Real career growth.

Information

  • Creator
    Fixify
  • Years Active
    2025 - 2026
  • Episodes
    9
  • Rating
    Clean
  • Copyright
    © Fixify
  • Show Website
    Climbing the Stack