20VC: PagerDuty CEO Jennifer Tejada on A Leader’s Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL).

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In Today’s Episode You Will Learn:

1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent?

2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen’s decision making process changed? How does Jen encourage debate and free thought sharing internally?

3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities?

4.) What have been Jen’s biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO’s structure their board in an optimal way? What do they need? What do they not need? How does scale change this?

5.) How does Jen think her style of leadership has changed over the years? What have been Jen’s lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here?

Items Mentioned In Today’s Show:

Jennifer’s Fave BookTuesdays With Morrie: An old man, a young man, and life’s greatest lesson

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