Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded?

Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the software giant behind products like Jira, Confluence, and Trello. Under his leadership, Atlassian has become one of the world’s most successful enterprise software companies, serving over 250,000 customers globally.

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others.

Timestamps:

• 00:00 Intro

• 01:06 Anthropic Predicts $149B in ARR in 2029

• 11:33 Mike’s Thoughts on SaaS Today

• 26:26 Harvey Raises $200M at an $11BN Valuation

• 45:56 Is Customer Support a Terrible or Terrific Investment Category?

• 01:00:58 Anthropic's Super Bowl Ad: Who Won & Lost

• 01:15:58 Do CEOs Have to Work Harder Today Than Ever