49: The AI Shift Every CTO Must Make (with Daryl Teo)

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested THE GUESTDaryl Teo is a technology strategist and seasoned CTO known for turning bold business vision into practical, scalable technical execution. Over the years, he has led engineering organizations of up to 150 developers, guided product and platform strategy across multiple industries, and built high-performance teams grounded in clarity, culture, and strong delivery. Today, Daryl advises companies as a fractional CTO—doubling down on AI-driven automation and transformation. With a rare blend of deep technical expertise and sharp business intuition, he brings the kind of leadership that helps startups, scale-ups, and SMBs move from idea to impact with confidence.THE SUMMARYSmall, agile teams outperform large ones: when rapid change is required. Working with compact, high-calibre teams lets leaders drive meaningful shifts in weeks instead of months — a pace larger organisations struggle to match thanks to bureaucracy and slow decision-making.Remote teams make junior hiring far harder: Without shoulder-to-shoulder mentoring, junior developers often become a net cost. In services-based environments, the margin pressure makes it almost impossible to justify the overhead of training juniors without a dedicated program.AI adoption starts with a mindset shift, not a technical one: The moment you stop treating AI as a novelty and start treating it like a collaborator — one whose output you audit with healthy skepticism — everything changes. This “AI-first” approach is now non-negotiable.The fastest wins come from augmenting existing capabilities: Some of the easiest, highest-ROI applications of AI aren’t glamorous. A 24/7 voice agent for a laundromat chain is a perfect example: humans sleep, machines don’t. Businesses gain capability they simply couldn’t afford before.AI is a weapon for speed in operational bottlenecks: Even shaving a few minutes off time-sensitive workflows — like sourcing inventory prices from multiple vendors — can materially shift conversion rates. AI becomes a force multiplier in places humans didn’t even realise they were inefficient.There’s no single “best” coding agent — the value is in speed, not purity: For rapid prototypes and short-lived projects, the differences between tools like Cursor, Claude Code, and Codex barely matter. What matters is delivering value, not endlessly comparing models.The most important advice for anyone entering AI? “Lean in and commit: Half-adopting AI is as useless as not adopting it at all. Treating models as capable collaborators — while still verifying their output — is the mindset that unlocks real leverage.THE SHOWWeekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.THE LINKSHave a question you want us to answer? Send it through to [email protected] TeoLinkedIn: https://sg.linkedin.com/in/thedarylteoMy linksLinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠ AI Career Boost: ⁠https://www.aicareerboost.com/⁠

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