Why Trello Failed to Build a $1 Billion+ Business

Good article today: Why Trello Failed to Build a 1bn+ business.

I wrote about Trello a year ago, when it was a clear leader for agile planning, with boards that were so simple and easy to use that they could be a natural part of a planning.  I’ve even done it via conference call, quick update and move the tasks priority/status in a way that was not possible with JIRA and other tools.

But the Trello upsell was never fully compelling.
I earned free months of “Gold” by signing up other users but the Gold service is only stickers, backgrounds and emoj.
Oh and the ability to upload a 250MB file (why??  Trello isn’t designed to be a video file sharing service or an app store…).

9.99 per user for unlimited integrations makes sense for core team members, but degrades the value of Trello as a publishing tool:  for example if you are using Trello to publish your roadmap/prioritisation to thousands of clients, you don’t want to make the board inaccessible/dependent on your clients having a Trello subscription.
As the article comments, from Drift:

When David Cancel, co-founder of Drift, put the company’s annual Trello bill on a slide — $1,700 — the entire team at Drift was shocked. As David says, “There are only a couple of people using [Trello] day-in, day-out. Meanwhile, however, we were being charged based on the number of people that we had in the paid plan. So clearly there was a disconnect between the price we were paying and the value we were getting.”

David downgraded his team from the paid plan to the free plan.

So what happened over the last year?    Core Development appeared to stop, perhaps due to the acquisition…

  • The markdown implementation is incomplete and not as easy to use as say Github.
  • Little niggles in the UI don’t seem to get improved (Save behaviour is inconsistent with some elements of the interface auto-saving, others too easy to click out of without saving).
  • The desktop app was finally released Sep 2017, great but would have been much more effective if released in Sep 2015.
  • Trello was acquired by Atlassian in Jan 2017 and in March new Trello power-ups were announced for Jira, Confluence, Bitbucket, Hipchat.

The Trello Dev Roadmap is itself a Trello board, which provides a nice summary as to what has been done, but no longer reveals much about what the plan is.

Atlassian development continues with the launch of Stride, to replace Hipchat and provide a more effective alternative to Slack and Microsoft Teams which has also been improving.  Stride is too new to pass judgement on right now, but the UI looks slick and Slack-like (ie much improved on previous generation of Atlassian products).  And if you need a version of Slack that is tied into Atlassian products, you’ll be trying Stride soon..

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