Asana’s Head of AI on the Profound Ways Work Is Changing | Paige Costello (Head of AI & Co-Head of Product Management at Asana)

CRAFTED. | The Tech Podcast for Founders, Makers, and Innovators

Paige Costello is the the head of AI and co-head of product at Asana and on this episode of CRAFTED. we're exploring what it means to ship products with AI, how AI will change the way work gets done, and how to organize your teams for success in this brave new world.

We explore:

• How the future of work – and communicating about work – is changing
• Why Asana chose to create an “AI org” instead of a less centralized innovation approach
• How Asana ships — and measures the success of — AI-powered features, e.g. SmartStatus, that aim to take the drudgery out of work
• How product management is changing with the rise of AI
• Why running an A/B test is harder when a non-deterministic (i.e. unpredictable by design) GenAI tool is involved
• Why it’s so important to “get out of the building” and some of Paige’s favorite user research moments from doing so
• The latest with “PaigeBot” and what Paige hopes AI can do for her

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CRAFTED. is produced by Modern Product Minds, where Dan Blumberg and team advise companies on product, discovery, growth, and experimentation.

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Key Moments:

[02:17] AI-generated status reports: How Asana summarizes a project – or many projects – using AI. And why it needs to do so carefully.

[05:00] How to organize for innovation: How Asana organizes its teams to integrate AI and the strategies they employ for effective AI implementation.

[09:06] How AI will change the role of product managers and why the stochastic nature of AI will be something we all have to get used to

[14:26] Challenges of prototyping and scaling AI

[16:07] How Asana uses AI internally and how it dogfoods its own products

[18:17] Profound implications of AI + the future of work

[22:20] Will AI really help product managers get out of the building more? Or do we just find new excuses not to? And what Paige finds so powerful about “being in someone’s space”

[25:32] An update on “PaigeBot” and what Paige wishes a bot would do for her