3 Incredible SaaStr Sessions with Stewart Butterfield, Co-Founder of Slack. And The End of One Era in SaaS.

So Slack is ending a bit of an era at $2B+ ARR, having been the fastest growing SaaS startup of its generation, rocketing to an incredible IPO, and then an epic acquisition by Salesforce in 2021 for $27 Billion!

Stewart Butterfield announced this week he’s handing the reins over now to Lidiane Jones at Salesforce.  It’s the end of one era and the beginning of another.

Slack has been a small part of SaaStr since the beginning.  At the first SaaStr Annual ever in 2015, Stewart was kind enough to be our final speaker, sharing the stage with David Sacks.  I knew the other speakers, but Stewart was just a cold outbound we did.  The only one I didn’t know.  But he was kind enough to come as our final speaker at SaaStr Annual #001.

That incredible session here, when Slack still didn’t have any traditional sales team:

Stewart then came back in 2018 to join Alex Konrad of Forbes and reflect on top learnings pre-IPO.  Slack was much bigger, and more B2B by this point, with a large enterprise sales team, and Stewart was in a much more contemplative mode:

Then … Covid and lockdown hit in 2020.  Everyone was really struggling those first few weeks.  My first ask was again … Stewart Butterfield.  I wanted a truly empathetic leader to teach us in the darker times of lockdown, how to Bridge the Gap.  And Stewart was again kind enough to come through:

Thank you, Stewart Butterfield, for building an app we all run our teams on.  Especially in these distributed times.  But especially, for being an inspiration.  The kind of leader we’d all like to work for.

I always felt Stewart was a bit uncomfortable with the crown.  Because he knew how hard it was.  Flickr, his startup before, had a real but modest impact (and possibly even inspired the name of a blog you may have read).  His gaming initiatives didn’t make it.  He even offered to give his investors their money back in the early days.  And he knew that the journey of building an amazing product was such a team effort, that focusing it too much on the one at the top was … too much focus.  He pushed his top executives, especially his women and less represented execs, to be a bigger public face as much as practical.

A humble and effective leader.  It’s really hard to do that right.  On behalf of the SaaStr Community, a toast to you, Stewart Butterfield.

Thank you for helping all of us.

Enjoy that gardening, Stewart.  You’ve certainly earned it.

And if the winds at some point blow you back into entrepreneurship, in one form or another.  Once the garden is fully tended, the traveling is complete. Well, you never know.