Tiago Azevedo is the CIO of OutSystems, one of the largest low-code development platforms in the world. In this episode, he sits down with Matt Paige to talk about what it actually looks like to lead through the chaos of enterprise AI adoption, why the old playbook of re-architecting legacy systems is dead, and how his team is building agentic solutions that bypass the mess instead of trying to fix it.

Tiago shares his philosophy that saying no to AI is the easy path, and that the real job of a CIO is to open the doors while learning to manage the risk. He breaks down why everything that isn't agentic is already legacy work, how his team uses AI to figure out where AI fits, and why companies should stop adding more fields and screens to broken systems and start building agents that do the work.

The conversation also covers OutSystems' latest launch, OutSystems Mentor, which brings natural language vibe coding into the platform so users can describe what they want and build it conversationally. Tiago explains the architecture behind it, including how the platform combines probabilistic AI with deterministic code generation, one-click deployment, and built-in enterprise integrations.

The episode closes with Tiago's advice for overwhelmed CIOs: identify the biggest problem your company needs to solve, feed it to an LLM with as much context as possible, and iterate from there. Think big, start small, scale fast.

In this episode, you'll hear about:

How Tiago approaches change management and AI adoption across a large organization. Why he believes everything non-agentic is already legacy. The "agents over apps" philosophy and what it means for enterprise systems. How OutSystems built Deal Mate, a team of agents that prepares sales reps for meetings. Why OutSystems achieved 40% automation in customer service after AI, up from under 10% before. The launch of OutSystems Mentor and what natural language app-building looks like inside the platform. The gap between a wow demo and enterprise-grade production. Why CIOs should try everything but be careful with divergence. Tiago's "think big, start small, scale fast" framework for AI transformation.

Key Moments:

• 01:17 — Tiago on the pace of change and what makes this moment unlike anything before
• 06:20 — "Saying no is the easiest solution — managing the risk is the hard part"
• 07:49 — Bypass the mess: why agents fill the gaps legacy modernization never could
• 09:10 — "Everything that is not agentic is literally legacy work"
• 10:15 — Use AI to figure out where AI fits: the meta approach to use cases
• 11:30 — Deal Mate: the team of agents that prepares sales reps for meetings
• 15:07 — "We were adding more fields to Salesforce when we should've been building agents"
• 16:25 — Mark Zuckerberg building an agent to do his job
• 17:23 — OutSystems' 20-year journey from visual development to agentic systems engineering
• 19:58 — The deterministic magic behind OutSystems Mentor
• 22:04 — One platform: infrastructure, integrations, UIs, agent skills, and deployment
• 30:19 — 40% customer service automation with AI (vs. under 10% before)
• 33:48 — How AI is augmenting, not replacing, engineering and product roles
• 39:41 — "That's 2008 and this is 2026 — you have to change"
• 41:27 — The wow factor vs. enterprise reality: why prototyping isn't the hard part
• 46:17 — Tiago's advice: identify the biggest problem, feed it to an LLM, build the solution
• 48:42 — "Think big, start small, scale fast"

Key Links:

• OutSystems
• Connect with Tiago on LinkedIn

Mentioned in this episode:

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