Scaling in the AI Era with PagerDuty CEO Jennifer Tejada

What It Covers

PagerDuty CEO Jennifer Tejada discusses enterprise AI adoption challenges, sales strategies for AI-era products, and provides feedback to four AI startup founders on observability, marketing automation, bug reporting, and workflow automation solutions.

Key Questions Answered

• •Enterprise AI Psychology Shift: Customer mindset evolved from FOMO (fear of missing out) to FOGI (fear of getting in) as organizations worry about security, cost overruns, and implementation failures rather than just wanting to participate in AI trends.
• •Discovery Over Speed in Sales: Sales teams must prioritize structured discovery processes to understand each enterprise customer's unique constraints, power dynamics, and regulatory environment rather than rushing to close deals based on pattern assumptions from previous customers.
• •Pricing Transparency Requirement: Consumption-based pricing models must include built-in instrumentation allowing customers to predict and control their bills transparently, as unpredictable costs create budget management problems that outweigh feature benefits in enterprise purchasing decisions.
• •Content Engineering for AI Search: Marketing teams need 2,000 FAQs instead of 20, structured for LLM ingestion with frontier knowledge (information models lack) rather than reorganized existing content to succeed in ChatGPT and AI-powered search channels.