Scaling in the AI Era with PagerDuty CEO Jennifer Tejada

Jennifer Tejada is CEO of PagerDuty, a public company serving 30,000+ customers worldwide. She joined Village Global GP Ben Casnocha for a masterclass on scaling in the AI era, followed by live feedback sessions with four founders building AI-native companies.

Takeaways:

• Enterprise sentiment has shifted from “fear of missing out” to “fear of getting in.” Customers are anxious about security, resilience, and managing the people transition.
• Know what gets your customer promoted and what gets them fired. Different personas care about different things. A CIO has different anxieties than a developer or CMO.
• Pricing is a strategic foundation, not a tactical enabler. Start with value realization for the customer, then build pricing metrics that tie back to that value. Consumption-based models are popular, but predictability matters more than novelty.
• Transparency is becoming an expectation. Customers want instrumentation in your product that makes their consumption and costs visible. Nobody likes surprises when managing margins.
• The AI transformation is moving faster than any previous shift. Old playbooks don't always apply. The people willing to embrace change and experiment with new ways of operating will win faster.
• Build your CEO village. Having a trusted network of other CEOs who understand the unique pressures of the role makes all the difference. Invest in that community on a daily basis.
• Psychology matters in people transitions. Asking employees to use AI to replace themselves won't work. Think differently about how you organize to get work done while helping people transition to where they can add value.

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