Climbing the Stack

Fixify

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.

  1. -3 j

    From engineer to C-suite: why financial fluency and storytelling separate real executives | Matthew Sharp

    Matthew Sharp came up as a computer and electrical engineer, moved through independent testing and audit work, and then took a sales role he was convinced would be the devil's work. Four years selling specialized security services taught him the opposite. He often walked into meetings knowing more about a client's business than the CISO across the table did, down to how they segmented revenue on their financial statements. Now CISO at Xactly and co-author of The CISO Evolution, his argument in this episode is that technical leaders stall on the climb to the C-suite because they cannot connect security to the business, and the fix is more concrete than the conference-stage line about speaking the language of business. That fix starts with learning to read the three financial statements, and he points to John Tracy's How to Read a Financial Statement for the single graphic that ties them together. He gets into moral authority versus formal authority from Covey, why he steers clear of the RFP as both buyer and seller, and the body, mind, heart, and spirit sabbatical (Everest base camp, the Camino de Santiago, Mandarin study, a month teaching English in Vietnam) that gave him cross-cultural empathy for why someone in a hard economy might turn to ransomware. At Xactly he walks through the India-based Center of Excellence, a Snowflake security data lake, a 24x7 AI SOC, and machine learning that forecasts the sales pipeline so his team clears cyber diligence on the deals most likely to close. He closes on where this goes next, with third-party diligence negotiated between MCP servers and a human in the loop, instead of an army of people slinging spreadsheets.   Topics discussed: - Reading the three financial statements to speak to executives - Moral authority versus formal authority in security leadership - Steering clear of the RFP as buyer and seller - Body, mind, heart, spirit sabbatical and cross-cultural empathy - India Center of Excellence built on a Snowflake data lake - Machine learning forecasting the sales pipeline to prioritize cyber diligence - Jobs-to-be-done hiring that scales with AI agents - Third-party diligence negotiated between MCP servers

    From engineer to C-suite: why financial fluency and storytelling separate real executives | Matthew Sharp

  2. 21 juil.

    A CEO sorted every employee into three AI buckets. Where would your team land? | Fred Bret-Mounet

    Fred Bret-Mounet, VP of Security, Compliance and IT / CISO at Accela, started his security career in 2001 at @stake, one of the handful of firms that invented security consulting. He was excellent at building Fort Knox. When he moved to the receiving end of those consulting reports, he realized recommending Fort Knox at all cost was the worst advice he could give. The framework he uses instead is the California speed limit. The sign says 65 or 75, but drive 85 without brandishing a gun or threatening anyone and there are no consequences. Those extra miles per hour are called velocity, and the CISO's job is to mark the line, explain what can be crossed, and let the business make an educated risk decision.   Fred tells Matt why AI has collapsed reinvention cycles from every five to ten years to six months, and how a CEO asked him to sort employees into three buckets: forward thinkers, trainable, and the resistance brigade. He grades his students on the same principle, failing anyone who submits AI as the end product and warning that skipping it as an input earns an F too. He predicts that organizations that do not automatically patch everything internet accessible will be dealing with breaches quarterly, if not monthly, by year end, since attackers will reverse engineer a patch in minutes. He also explains why your first line of response to security events must be entirely automated, and why he blows up relationships with his own team on a weekly basis, trading two-week fix demands for two months, to land the ideal business outcome.   Topics discussed: - Reinvention cycles collapsing from a decade to six months - Sorting employees into three AI adoption buckets - The Tesla full self-driving analogy for calibrating AI trust - Auto-patching everything internet accessible before attackers reverse engineer fixes - Fully automated first response to security events - Detecting phishing through intent rather than message syntax - The speed limit framework for advising on business risk - Publicly disavowing your team to reach the right business outcome

    A CEO sorted every employee into three AI buckets. Where would your team land? | Fred Bret-Mounet

  3. 7 juil.

    CIO vs. CISO: Resolving the ROI-versus-risk conflict when you hold both | Georgeo Pulikkathara

    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 also lays out how he presents security budget to boards: tied to specific revenue deals, never to abstract risk ratings, with three solution options already on the table (the premium version, the cheap version, and the one most organizations actually choose) so he never has to go back for emergency money mid-year. He shares PFC Romeo, the military decision framework now embedded in his IT org: Problem statement, Facts (objective only, no opinions), Considerations (political, emotional, who's going to take it the wrong way), Recommendations (always two viable options, not one good and one bad). He walks through his tiered security architecture, anchored at Tier 0 with identity and MFA through production cloud environments and CI/CD pipelines, and explains why he operates from the assumption that attackers have already bypassed endpoint protection tools like Defender ATP and are targeting identity and production infrastructure instead. That assumption comes from experience: when an AI company became a client, his team detected 13 North Korean threat actors in a single week, running IP proxies and AI-generated faces to get past HR screening that most organizations aren't built to catch. He closes with the 2016 interview at Santander Consumer Bank where the CSO laughed so hard at his five-year CISO prediction that he refused to hire him, and what Georgeo built in that window to prove it right on schedule. Topics discussed: Using CIO budget to fund security controls directly Building financial fluency through a 4-5 month SMU program pre-C-suite Real-time back channel coaching IT leads during live client calls Tiered security model anchored at Tier 0 identity with endpoint bypass assumption Tying board security asks to specific revenue deals with three solution options PFC Romeo framework for structured team escalations and decisions Physical printed incident response plans for ransomware network lockout Detecting North Korean threat actors through IP proxy and AI identity controls

    CIO vs. CISO: Resolving the ROI-versus-risk conflict when you hold both | Georgeo Pulikkathara

  4. 2 juin

    “Enabling chaos": how AppsFlyer hit 97% AI adoption across 1,300 employees | Chily Fachler

    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

    “Enabling chaos": how AppsFlyer hit 97% AI adoption across 1,300 employees | Chily Fachler

  5. 28 avr.

    "Someone who uses AI better than you will replace you": building fluency inside IT | Guillermo Porcaro

    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

    "Someone who uses AI better than you will replace you": building fluency inside IT | Guillermo Porcaro

  6. 14 avr.

    From bicycle sales to CIO: how a non-technical path accelerated leadership | Bryan Wise

    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

    From bicycle sales to CIO: how a non-technical path accelerated leadership | Bryan Wise

  7. 3 mars

    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

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

  8. 17 févr.

    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

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

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.

Informations

  • Création
    Fixify
  • Années d’activité
    2025 - 2026
  • Épisodes
    15
  • Classification
    Tous publics
  • Copyright
    © Fixify
  • Site web de l’émission
    Climbing the Stack