Ok the title isn’t fair.  I have far, far more than 5 favorites from 4+ years of the SaaStr Annual.  Interviewing Aaron Levie just weeks after Box’s IPO in 2015.  Talking with Stewart Butterfield about if Slack would ever add a sales team.  The amazing interview of Michael Pryor, CEO of Trello with his boss, Michael-Cannon Brookes, CEO of Atlassian.  Those are all amazing sessions, among many others, that I think about to this day.

But if I had to pick 5 sessions that resonate personally with me, these are probably the top 5.  Let me share them — and why.

I loved this discussion with Lew Cirne, founder/CEO of New Relic. He’d already started an amazing company, sold it for $400m … and decided he had to do it all over again. In the same space. Why? And what did he learn? And what did he actually get wrong the second time? New Relic is worth $6 billion today.  We don’t often get second shots at it, especially after the first chance was a huge success.  That’s so interesting to me.  And Lew is truly a founder’s founder.  The best of the best.  A thoughtful, brilliant, people-centric hacker who learned to love sales 😉  Who I wished I was, as a founder and CEO.


The Myths of Start-up Success with CEO of Blackline, Therese Tucker. This was one of the top 3 most popular sessions of all time. Therese did it the hard way, Blackline struggled for years, she did it as a seasoned female CEO when doors were shut to her left and right.

Today, Blackline is worth $3 billion.

It is incredibly inspirational:

How to Really Hire a Great VP of Sales, with Jennifer Lawrence, VP Sales at Duo Security, and Brendon Cassidy, ex-VP of Sales, Linkedin, EchoSign, Talkdesk. We’ve done a ton of stuff on hiring a VP of Sales but boy this is my personal favorite. Jennifer is terrific, and Duo Security was just bought by Cisco for $2.3 billion.  This session wasn’t promoted as much as it should have been due to a gap in SaaStr.com programming, so this is probably the first time you are seeing it.  Trust me, watch it.  We’re also extremely fortunate to have Duo’s CEO Dug Song speaking at the 2019 Annual!

Peter Gassner, CEO and founder of Veeva Systems. Veeva got to a $15 billion valuation raising less than $10m in venture capital, selling to the enterprise. It sounds impossible. But it’s not when you have one of the best founders I’ve ever gotten to know:

Build, Break, Stretch, Repeat Lessons from Scaling Google & Stripe, with Stripe COO Claire-Hughes Johnson. This was the #1 rated session from the 2017 Annual. Claire is an operator’s operator, and her insights resonated with the audience in a profound way I hadn’t fully expected.  It’s a good one, with a lot to digest.  We’re incredibly fortunate to have Claire back for the 2019 Annual!

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