Structured decision-making processes and review cadences for managing technology assets, vendor relationships, and infrastructure refresh cycles in organizations.
3 episodes
Jim Hasty, founder of Cogle Group, discusses his company's evolution from technology consulting to AI-powered software products. He shares lessons from building Plan Checkers, an AI tool that reduces municipal permit review time from weeks to minutes, and outlines a crawl-walk-run framework for enterprise AI adoption focused on automating emotionally draining tasks rather than chasing adoption metrics.
Kirby Winters discusses launching multiple ventures simultaneously using AI-powered development, including Cyber Savi (a compliance automation platform), a vodka brand, and Unshucked (an oyster tracking app). He explains how agentic AI enables building production-ready software in weeks instead of years, the shift from consulting to outcome-based services, and strategies for selling cybersecurity compliance tools through MSP channel partners.
Three fractional IT executives discuss cost optimization strategies during economic downturns, including cloud infrastructure waste, vendor management, and strategic hiring decisions. They share specific examples of reducing AWS spend by 50-75%, eliminating unused software licenses, and the risks of cutting technical staff without preserving domain expertise.
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