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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
