
EP 122: Okta CEO Todd McKinnon on Scaling to $13B, High-Stakes Decisions, and Market Dynamics
The Logan Bartlett ShowShow Notes
What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft. Todd also reflects on his journey to founding Okta, his bold choice to team up with a co-founder he hardly knew, and the motivations that have fueled him for over seven years as a public company CEO. Some key takeaways…
[0:00] Intro [0:33] Todd McKinnon's Early Career and Founding Okta [1:38] Challenges and Psychological Shifts in Leadership [2:49] Decision Making and Company Culture [6:10] Milestones and Early Successes [18:03] The Importance of Market Timing [30:34] Hiring and Building a Strong Team [39:22] Setting Expectations with Board Members [40:50] The Shift in Board Dynamics [41:41] Maintaining Context and Strategic Input [43:15] Navigating Public Company Governance [45:21] Trusting Instincts and Founder Mode [47:11] Breaking Out of the Echo Chamber [51:00] The Importance of Prioritization [53:05] The Loneliness of Innovation [1:05:33] The Role of a CEO in Decision Making [1:18:17] The Journey to IPO and Beyond
Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
Follow on Socials
📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow
About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.
More from The Logan Bartlett Show
Bret Taylor is the CEO of Sierra and Chairman of the Board of OpenAI. He previously served as co-CEO of Salesforce. I sat down with Bret to explore how the AI revolution compares to previous platform shifts and what it means for both startups and incumbents navigating this transition.
Logan is joined by Marc Benioff, the legendary co-founder and CEO of Salesforce, for a wide-ranging conversation on the rise of AI in enterprises. Marc explains how Salesforce has become the testing ground for its own “agentic” technology, using AI agents to handle customer support, boost sales, and transform marketing. He also shares his perspective on what’s hype vs. reality in the AI race, the opportunities for startups, and why the future is about humans and agents working together.
Joe Hudson is the founder of The Art of Accomplishment and has worked with many top leaders in Silicon Valley, including Sam Altman and executives from Apple, Google, the NBA, and more. He coaches the research and compute teams at OpenAI and works with all the major AI companies.
Chris Degnan is one of the most legendary CROs of this generation. He joined Snowflake as employee #13 and the 1st sales hire. He scaled the sales org from 0 to over $3B in ARR, spanned four CEOs, and retired as CRO after 11 years.
Logan sits down with Bipul Sinha, CEO and co-founder of Rubrik and former VC at Lightspeed and Blumberg Capital. Bipul shares what he learned transitioning from investor to founder, why intuition beats expertise, and how he built Rubrik into a category-defining business by betting on uncool ideas. They talk product-market fit in the AI era, what most VCs get wrong today, and why the enterprise IT market is still just getting started. It’s a conversation packed with hard-earned wisdom and bold takes on building lasting companies.