(2017-10-16) Shah Why Trello Failed To Build A $1 Billion Business

Hiten Shah: Why Trello Failed to Build a $1 Billion+ Business

In 2011, Joel Spolsky launched his company Fog Creek’s new product at TechCrunch Disrupt called Trello.

Trello was successful building this horizontal product, achieving rapid growth to tens of millions of users and an acquisition of hundreds of millions of dollars. However, the one thing Trello didn’t do a good job of was keeping track of it’s paying customers. Trello was so focused on building its free customer base first and monetizing later; by the time it looked to its paid subscribers, it was too late — they’d already moved on.

The product vision was to strip everything down and build around the visual idea of cards on boards

All of this stuff was new at the time, and gave Trello a lot of runway. But by 2016, it wasn’t as hard to a build beautiful and responsive web app like Trello, and you started seeing Kanban boards everywhere

• GitHub builds Kanban boards in September 2016
• Asana announces Kanban Boards in November 2016:
• Airtable Launches Kanban Boards in November 2016

“We see Trello as a feature, not a product.”

Trello might have become a $1B+ business if it looked like a “system of record” application — the single-source of truth for a company. Imagine if you could use Trello not just to track your marketing funnel, but to move information from your marketing board to your sales pipeline and product roadmap. Instead of having a separate Trello board for each team, you’d have a big board for the entire company.

Trello could have doubled down on upselling individual consumers to paid plans. They could have focused on building features for SMB customers. Or they could have expanded into the enterprise faster. Any one of these things would have led to a $1B+ valuation. Let’s talk about what Trello could have done with each path, starting with its consumer plan.

#1) Trello Didn’t Monetize Free Fast Enough

Three years after launch, Trello’s growth in users looked on track to explode past Dropbox’s levels, at 10 million in 2015 (Dropbox had four million three years after launch). But Trello had a much harder time upselling free customers to its paid “Trello Gold” plan.

Trello’s value proposition is harder to locate than Dropbox, which is exactly why Trello should have figured out early what features individual consumers were willing to pay for.

Solution: Dig Into the Freemium Use-Cases

Instead of focusing on building a wide product for everyone, Trello should have dug deeper into its use cases in the beginning to figure out why people were signing up, what they were using the product for, and what people found so valuable that they’d be willing to pay to use Trello.

Let’s say Trello found out that of its freemium user base, lawyers, real estate agents, and designers had the highest revenue potential. They might have learned that while designers want access to a calendar in their Trello boards, lawyers want read-only boards that they can share with clients.

Trello could have created a separate landing page to re-target free customers and upsell them to a paid plan according to their specific use cases.

#2) Trello’s Product Wasn’t Sticky Enough for SMBs

Solution: Build Out Better Integrations for SMBs

Imagine the ability to open and close GitHub issues inside of Trello. Imagine if all of your Salesforce leads automatically opened and closed on a Trello board based on what you did inside of Salesforce

#3) Trello Didn’t Build for the Enterprise

Solution: Become the System of Record for the Enterprise

The vision behind Slack.com’s enterprise product is that it allows organizations to “create more or less any kind of structure” with Slack