What if you had to step into a CEO role at just 22, with no formal business training? That’s exactly what Thiago Da Costa did, and he quickly discovered that leadership is best learned on the job. In this episode, Thiago shares what it was like to build and grow a company that Autodesk later acquired, leading teams of up to 300 people and adapting to constant organizational change. He reflects on the lessons learned about authenticity, cultural alignment, and the compromises leaders must navigate to stay true to their values while driving results.

You’ll also hear how Thiago is now leveraging AI to shape the future of work. From hiring and skill development to automating routine tasks, Thiago offers a fascinating look at how AI can enhance—not replace—human leadership. He shares practical insights about using AI for personalized guidance, preparing for tough conversations, and freeing leaders to focus on what matters most: engaging meaningfully with people. His vision of AI as a partner in leadership offers a compelling roadmap for today’s leaders who want to stay relevant in a rapidly changing world.

Thiago is a product visionary, an AI futurist, and a serial entrepreneur. He sold his first company to Autodesk and is now building the future of work with Datagrid, where he’s Founder and CEO. Datagrid is an AI platform that turns your company’s data into intelligent agents. These agents automate workflows, surface real-time insights, and supercharge decision-making.

You’ll discover:

The hard-earned lessons Thiago acquired as a first-time CEO at 22.
Why aligning with an organization’s culture and DNA is essential.
How AI agents are transforming routine business tasks.
Ways AI can enhance communication and feedback for leaders.
The future of hiring in an AI-driven workplace.

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351: Navigating Leadership in the Age of AI