Todd McKinnon

Co-founder and CEO of Okta, and the central subject of Todd McKinnon — Creating and Defining a New Market Category — Patrick O’Shaughnessy’s Invest Like the Best interview that Kyle annotated heavily. McKinnon ran engineering at Salesforce before leaving in 2008 (into the financial crisis) on the thesis that the whole stack — apps, collaboration, infrastructure — was moving to the cloud, and that the shift would create demand for new tools. Okta began as a cloud-app monitoring idea (“SaaSure”) but pivoted early to identity management when IT buyers kept surfacing one acute pain: they couldn’t log in to their new cloud apps.

The interview is Kyle’s reference text for several company-building themes: threading the timing needle (building before the market obviously needs it, but not so early it “falls on a world that doesn’t need it”), enduring the doubt required to create a category and become the default (“cognitive referent,” like Kleenex or Stripe), and the second act — customer identity (CIAM) — emerging from customers (Allergan’s doctors, MLB.com) rather than a plan, eventually ~24% of revenue. McKinnon’s early mistake was importing Salesforce’s small-company go-to-market wholesale; correcting it via first-principles thinking (“the more users you have, the bigger the problem is,” so sell to the biggest customer you can) is a clean case study Kyle flags. He also articulates leadership as clarity plus admitting you don’t have the answers, and the software economics of high gross margins + big TAM rewarding growth.

Context: Todd McKinnon is the co-founder and CEO of Okta, the publicly traded (Nasdaq: OKTA) enterprise identity and access management company he started in 2009 after running engineering at Salesforce.

Where this appears

• Todd McKinnon — Creating and Defining a New Market Category — the long-read interview where McKinnon recounts leaving Salesforce, the Okta pivot, category creation, and his frameworks for innovating as a public company.