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20VC: Okta CEO Todd McKinnon on How To Approach Effective Decision-Making in Leadership, When Is The Right Time To Hire Recruiters and Heads of People, Balancing the Expectations of Wall St with Long Term Vision and What Truly Successful Board Management

Feb 22, 2021

Todd McKinnon, Co-founder and CEO of Okta, shares his journey from stable jobs at PeopleSoft and Salesforce to founding a leading identity security company. He dives into effective decision-making frameworks, exploring the difference between reversible and irreversible decisions. McKinnon discusses the crucial timing for hiring recruiters and heads of people, emphasizing the need for the right talent. He also reflects on managing board dynamics, balancing Wall Street's expectations with long-term vision, and the importance of vulnerability in leadership.

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INSIGHT

Decision-Making Prep

Prepare for impactful decisions by continuously gathering information and context.
Avoid cramming; preparation allows for better head-versus-heart decisions.

ADVICE

Persistence in Entrepreneurship

The most important trait for enterprise software entrepreneurs is persistence.
Believe in your vision even when facing adversity and intellectual doubt.

ADVICE

Prioritize Hiring

Prioritize hiring and talent acquisition, even in early stages.
Invest in full-time recruiters early on, rather than relying solely on contingency firms.

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Todd McKinnon is the Co-Founder & CEO @ Okta, the identity layer for the internet, providing one trusted platform to secure every identity, from customers to your workforce. Prior to their IPO in 2017, Todd raised over $229M for the company from some of the best in the business including Sequoia, a16z, Greylock, Khosla and Floodgate to name a few. Prior to founding Okta, Todd was VP of Development @ Salesforce.com where he spent an incredible 5 years and before that enjoyed an 8 year run in the software development team @ PeopleSoft.

In Today's Episode You Will Learn:

1.) How Todd made his way into the world of startups with PeopleSoft and Salesforce? What was the a-ha moment for Todd with the founding of Okta? What were the biggest management takeaways from his time with PeopleSoft and Okta? How did Todd convince his wife that leaving a safe job with Salesforce to found a company was the right decision?

2.) How does Todd approach decision-making today? What frameworks does he use to optimise his decisions? How does Todd analyse reversible vs irreversible decisions? How does Todd know when he has done enough work and is ready to make the decision? Who does he debate the most important decisions with?

3.) What does Todd believe makes for a truly great enterprise software entrepreneur today? What were the first elements to break in the scaling of Okta? When is the right time to hire your first recruiters and Head of People? What should you look for in those people? How did Todd make mistakes when it comes to hiring recruiters?

4.) What are Todd's biggest lessons on successful board management? How would Todd describe his style of board management? How has it changed over the years? What can CEOs do to extract the most value from their board? What were the biggest mistakes Todd made in the early interactions with his board?

5.) How does Todd balance the growth expectations of Wall St on a quarter by quarter basis with the long term vision and strategy? Why does Todd believe that Okta has been able to make the transition from unsexy to one of Wall St's most loved companies? What is the secret to investor relations as a public company?

Item's Mentioned In Today's Episode

Todd's Favourite Book: Slaughterhouse 5

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