Teach Your Team to Thrive with AI feat. Hannah Calhoon from Indeed

How do you bring your entire organization along for the AI ride while inspiring confidence and flexibility amid fast evolution? Hannah Calhoon, VP of AI and Head of AI Innovation at Indeed, shares how she’s helping 11,000 employees embrace AI as a partner in their work.

Host Francois Ajenstat gets things going through an exploration of how AI is currently transforming Indeed in both its offerings and the way its teams work every day. Hannah explains a focus on balancing rapid experimentation with thoughtful change management, and why building role-specific skills has been key to adoption thus far.

You’ll hear how Indeed trains teams across engineering, sales, and marketing to use AI tools effectively, how a “Lego block” approach helps them stay flexible in a fast-moving space, and why human judgment still sits at the center of AI-powered hiring.

Hannah also shares lessons on creating safe spaces for experimentation, overcoming resistance to new tools, and leading large-scale change without losing trust. Whether you’re scaling AI in a global enterprise or navigating your first AI initiatives, this episode offers a practical blueprint for transformation at speed.

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Guest Bio

Hannah is a VP of Product at Indeed, where she leads the AI for Indeed team. Her team focuses on enabling everyone at Indeed to effectively build and use AI tools and preparing the organization for the Future of Work. She also chairs the cross-company AI steering committee, which is tasked with ensuring Indeed is moving quickly and responsibly to deploy AI to drive business outcomes. 

Previously, Hannah led Indeed's long-term innovation team and built out Indeed’s GenAI Lab. She has focused her career on building innovation systems that deliver benefits to people's daily lives—initially in pharma and medtech and for the last 10 years in software, with a focus on fintech, legal tech, and HR tech. 

Hannah holds degrees from Harvard College and Stanford's Graduate School of Business. She serves as a Venture Partner for Purpose Built Ventures and sits on the board of edtech nonprofit Economic Mobility Systems.

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Guest Quote

"We sort of think of the world like we're building an architecture with Lego blocks. And so you've got your moderation block, and right now we have one or multiple solutions, either first party or third party, for moderation. But we're building the system so that if two years from now there's a much better way to do moderation, we can effectively pull that block out and stick a different block in. So we are architecturally optimizing for flexibility under the assumption that the choice that’s right today is almost certainly not going to be the choice in three years." – Hannah Calhoon

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Time Stamps  

00:00 Episode Start

01:25 Hannah's AI role at Indeed 

04:45 How to implement AI tooling internally

08:30 Overcoming resistance and gaining trust

11:40 Think of AI strategy like building Lego

13:40 You don't always need the latest and greatest

16:30 Who should be responsible for AI strategy?

18:50 The unintentional impact of AI

21:50 Supercharging humans with AI tools

26:15 Change management in driving AI adoption

29:30 Is the danger of bad actors worth losing sleep over?

35:10 Hannah's "Oh Sh*t Moment"

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Links

• Connect with Hannah Calhoon on LinkedIn
• Check out Indeed
• Connect with Francois Ajenstat on LinkedIn
• Check out Amplitude