Navigating AI in Corporate Culture and Lighthearted Tennis Gossip

AI is evolving so fast that it’s hard to keep up—sparking both excitement and anxiety about the future of work. Will AI replace jobs, or will it redefine them?

In this episode of [Un]churned, host Josh Schachter, SVP of Atlas at Gainsight, sits down with Jeffrey Bussgang, General Partner & Co-Founder at Flybridge Capital Partners and Senior Lecturer at Harvard Business School, and Teresa Anania, Chief Customer Officer at Sophos, who’s been leading from the frontlines of AI-driven customer engagement. Together, they unpack the gap between the theory of AI transformation and the reality of implementation in large organizations. Jeff discusses how leaders can foster an “AI native” culture—one that encourages experimentation while valuing human judgment. Teresa shares a candid look into Sophos' AI journey, addressing the fears, resistance, and cultural shifts that come with change. She also highlights practical strategies to empower teams and enhance customer experiences through thoughtful automation.

Whether you’re a tech leader, customer success pro, or just AI-curious, this conversation is packed with actionable insights on embracing the future without losing the human touch.

Timestamps:

0:00 - Preview

0:48 - Meet Jeff & Teresa

2:40 - The Impact of AI on Business Innovation

5:00 - Fostering an AI-Driven Culture to Elevate Workforce Value

16:10 - How AI Enables Rapid Prototyping

19:40 - Balancing Human and AI Workflows

21:50 - Quality Assurance and Customer Experience at Scale

27:50 - Internal “Agent Assist” Solutions

35:07 - Dynamics in Adopting AI Solutions

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👉 Follow the podcast

Subscribe: https://www.youtube.com/@Gainsight

Apple Podcast: https://apple.co/3dfWXmD

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👉 Explore more episodes, takeaways & transcripts: https://gainsight.com/unchurned

👉 Connect with the guests

Jeffrey Bussgang: https://www.linkedin.com/in/bussgang/

Teresa Anania: https://www.linkedin.com/in/teresa-anania/

Check out Jeff's Book “The Experimentation Machine": https://experimentationmachine.com/

👉 Connect with host

Josh Schachter: https://www.linkedin.com/in/jschachter/

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[Un]Churned is presented by Gainsight

About Gainsight

Gainsight is the retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. Learn more at www.gainsight.com.