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Scaling in the AI Era with PagerDuty CEO Jennifer Tejada

47 min episode · 2 min read
·
Pagerduty Ceo Jennifer Tejada

Episode

47 min

Read time

2 min

Topics

Startups, Leadership, Marketing

AI-Generated Summary

Key Takeaways

  • 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.

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.

Notable Moment

Tejada challenges the founder-CEO transition dynamic by stating experienced executives will reject CEO roles where founders retain control of finance and product, as this removes the autonomy required to actually lead and operate the business effectively.

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Episode Transcript

Hey, everybody. This is Ben Kesnoka, cofounder and partner at Village Global, a network driven venture firm. And this is our podcast where we go deep on all things business and technology with world leading experts. Good afternoon. Good evening. Wherever you are dialing in, I'm Ben Casnoka, partner here at Village Global, and we're delighted to have Jen Tejada, who's CEO of PagerDuty. Many of you know PagerDuty. She's helped scale the company from promising little startup to now, of course, a public company, 30,000 plus customers around the world. And, she's also an LP here at Village Global. Our plan for the next fifty five minutes or so is Jen and I are gonna chat for about twenty minutes on the state of PagerDuty, the impact of AI, maybe some tips and tricks on how each of us can accelerate our go to market and sales motions. Then we're gonna shift and invite four successive founders to join the conversation one by one. They'll each have five or six minutes to talk about what they're working on, show a quick demo, solicit some input and reactions from Jen, and then we'll wrap up. So Jen, welcome. Thanks for doing this. Thank you. Thanks so much for having me. So let's start just to orient everyone and level set. Tell us the state of PagerDuty today. What's the current product offering and scale for those who aren't aware? I mean, there's not really never been a more exciting time to be a PagerDuty. I always say say to people, like, when you're the CEO, there's no getting promoted. So you have to reinvent yourself and find growth opportunities in disrupting the business, disrupting yourself, finding new paths to growth, finding new markets, solving new problems. And, you know, I think as somebody who's been in this industry for a number of decades now, we really have just never seen a transformation or, like, the tectonic shift that we're seeing with AI move so fast. You know, I was around for the smartphone transition. It was the year of mobile for ten years. Right? Cloud, you talk to any of the cloud providers, they'd tell you there's still a long way to go in cloud adoption. That's not a mature market in their view. But the AI transformation is just happening so fast. You know, we're seeing such a different pace and velocity of change, and it makes for some uncomfortable moments, you know, because a lot of the old playbooks that you would throw at some of these business challenges don't apply. But at the same time, it makes for really exciting moments. I was in town hall yesterday, and I said to my employees, like, there's no limit on your capacity if you figure out how to deploy AI against some of the challenges and opportunities you're trying to address. So in this world where we needed a new person and our new skill set to do something, …

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