Going Upmarket, And How Things Have Changed in a Decade, at Trello, with Founder Michael Pryor

The other day we had a chance to catch up with Michael Pryor, founder of Trello, on what’s changed over a decade at Trello, and after crossing well more than 50,000,000+ users.

The session is here, and some key take-aways below:

Some of my top learnings:

1. Software per se doesn’t always last decades — but brands do.  Michael had a great point that while the Trello of 2030 may not resemble the Trello of 2012 all that much, there’s a 100% likelihood the product and brand will exist then.  Once you have a brand, even a mini-brand, you have to nurture it.  Take care of your customers, your brand, your mission, and reboot what you do every few years … and your brand at least can last decades.  Even if the product changes a lot.

2. Viral products can stay viral forever.  We talked about at 50,000,000+ users (a lot more, really) if Trello had seen a decrease in the percent of users acquired virally.  The answer was no.  That’s what you’d expect, but it is good to hear.  If you have even a lightly viral product — go long there.  It’s OK if the viral coefficient is low.  As long is it’s there, it can boost growth for decades.

3.  It’s easy to make your product more complicated.  While we all know this, it was reassuring to hear from Michael that as Trello heads into its second decade as a product, keeping it “simple” while making workflows more and more sophisticated remains a top challenge.  It’s part of maintaining any great software product that requires little training.

4. Indeed, Trello obsesses about not requiring training — even as it goes more and more enterprise.  You can hack a product that’s hard to use and/or hard to onboard with people.  And that’s common in the enterprise.  But if you want a product accessible to everyone, you can’t go down this path.

And take a fun look back at where Trello was right after Atlassian acquired them for $400,000,000+ here:

Published on November 8, 2020

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