AI Impact

Larridin

CIOs are being handed massive AI budgets and board-level pressure to prove value. This show features conversations with technology leaders about what's actually driving impact, what's not, and how they're making the case to skeptical executives.

Episodes

  1. Who Owns the Bot? Bask Iyer on AI Accountability, Pretotyping, and the Vendor Trap

    12 MAY

    Who Owns the Bot? Bask Iyer on AI Accountability, Pretotyping, and the Vendor Trap

    Bask Iyer has held the global CIO seat at Johnson & Johnson, Honeywell, VMware, and Dell, and now advises over a dozen AI companies including Zoom and ThoughtSpot. In this episode, Russ gets into how enterprise technology decisions actually get made, and how AI is exposing the real cost of CIOs, CFOs, and heads of HR operating without a shared accountability model. Bask makes the case that most AI pilots are theater, that cost avoidance is not a real business result, and that the safest-looking vendor decisions are quietly destroying a CIO's ability to differentiate. He also shares the specific framework he uses to get CEOs out of their own way without winning the argument. Topics Discussed: Why CIOs at tech companies can't lead with technical authority, and the Eric Clapton framework Bask uses to hold his position anywayThe agent accountability gap: who owns the bot that just discounted your inventory 30% on Thanksgiving, and why CIO, CFO, and HR have to answer that question togetherWhy task-specific agents are breaking the case for monolithic ERP, and what that means for how CIOs should think about build vs. buy todayWhat enterprise founders consistently get wrong about selling outside Silicon Valley, and why Bask has to shock them into leaving their zip code"Pretotyping": the one-month framework Bask uses to pressure-test a CEO's AI conviction without a nine-month proof of conceptWhy "the tool saves me time on weekends" fails the CFO test, and what actual productivity impact has to show up on the bottom lineThe case against splitting the CIO and Chief AI Officer roles, and what Bask tells boards when they askWhy letting Gartner pick your stack leaves you with no budget left to differentiate, and why Bask tells younger leaders to validate vendors over coffee in Silicon Valley instead

    33 min
  2. ClickUp's CFO on the AI Investment Framework That Actually Scales

    23 APR

    ClickUp's CFO on the AI Investment Framework That Actually Scales

    Dan Zhang has been CFO of ClickUp for five years, with an unusually broad remit spanning finance, accounting, legal, HR, and operations. That vantage point shapes everything he shares here, from his 2x2 vendor evaluation framework built around autonomy and attribution, to his three-bucket system for measuring AI ROI across a finance team, to the exact methodology his team used to shift skeptical analysts from "I don't think AI can do my job" to "I can test my hypothesis in seconds instead of hours." He also gets into two new hiring profiles he is actively recruiting for, why curiosity and humility have replaced domain expertise as his primary criteria, and how AI is already rewriting the corporate math on enterprise AE quotas, sales engineer ratios, and back-office headcount models. Topics Discussed: The autonomy-attribution 2x2 for deciding which AI vendors get scaled, monitored, or sandboxed Three-bucket finance ROI framework: 1-to-10 automation, new capability creation, and quality boost Why top-down alignment combined with bottom-up organic adoption is the only way to roll out AI successfully across a company The live offsite methodology that converted finance team skeptics into believers through real-time edge case testing Why the board doesn't want quick wins: tailoring AI impact messaging across frontline employees, business leaders, and investors Two new hiring profiles replacing traditional functional expertise: the context optimizer and the insights interrogator How AI is already rewriting corporate math on enterprise AE quotas, sales engineer ratios, and back-office headcount models Why curiosity and humility, not domain expertise, are now the hiring criteria that determine who succeeds in an AI-first environment Listen to more episodes:  Apple  Spotify  YouTube

    45 min
  3. Superpowers: How Jesse Built the #1 AI Coding Workflow — and Stopped Writing Code

    9 APR

    Superpowers: How Jesse Built the #1 AI Coding Workflow — and Stopped Writing Code

    Jesse Vincent is the creator of Superpowers, the most installed skills framework for Claude Code, with over 100,000 GitHub stars in its first five months. Superpowers isn’t a prompt or a collection of tips—it’s a complete software development methodology built for a world where agents do the building. Jesse has been shipping open source for 30 years—he created Request Tracker, led Perl 5, built K-9 Mail (now Thunderbird for Android), and co-founded Keyboardio. His last hand-written line of code was October 2025. He’s never been more productive. In our in-depth conversation, Jesse shares: The full Superpowers workflow: Socratic brainstorming → design spikes → spec writing → spec review → implementation → code review—and why skipping any stage breaks the whole thing Why the brainstorming phase is designed to trick you, not the agent—and the consulting technique behind it Why specs have replaced code as the only artifact humans should review—and how cross-reviewing specs between multiple Claude instances catches what a single pass misses The orchestrator pattern: a coordinating agent that dispatches pinned tasks to sub-agents, each with an ephemeral spec-review agent that enforces quality before any code ships Why most implementing agents could run on Haiku instead of Opus—and what that means for cost and speed The “fresh eyes” prompt that causes agents to step back and actually think critically—and why managing agents is eerily similar to managing humans Why saying “I love you” to Claude measurably improves output—and how persuasion principles from Cialdini’s Influence transfer directly to frontier AI agents His advice to developers: the spec is your leverage now—learn to write clearly, decompose problems well, and let the agents grind

    49 min

About

CIOs are being handed massive AI budgets and board-level pressure to prove value. This show features conversations with technology leaders about what's actually driving impact, what's not, and how they're making the case to skeptical executives.