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

Aug 28, 2020

In this engaging conversation, Jennifer Tejada, CEO of PagerDuty, shares her journey from consumer marketing to the forefront of enterprise leadership. She reveals how she navigates risk and insecurity while making decisions with imperfect data. Tejada emphasizes the importance of fostering a culture of healthy debate within teams and outlines her strategies for effective board management. She also discusses the critical need for diversity in tech, advocating for transparency and accountability in leadership roles.

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ANECDOTE

Jennifer's Career Path

Jennifer Tejada transitioned from consumer marketing at P&G to the tech industry due to her interest in the internet.
Her path included supply chain automation at i2 technologies and leadership roles at Keynote Systems and Mincom before joining PagerDuty.

ADVICE

Advice for Graduates

Graduates should prioritize companies, like PagerDuty, that invest in employee growth and development.
Focus on foundational skills, cross-functional experience, and self-discovery instead of rushing to the top.

ADVICE

Balancing Pace and Growth

Focus on intrinsic motivations, not external pressures, to guide career decisions.
Prioritize learning and value creation to find fulfillment and set your own pace.

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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 Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson

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