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See Stack Overflow Grow: How To Keep Your Company On Track In Trello

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Jack Sinclair is the CFO at Stack Overflow, the largest online community for developers to drop knowledge, learn new skills, and develop as professionals. With over 40 million visitors each month and groundbreaking new initiatives like the Developer Story, Stack has seen tremendous growth since it was founded in 2008. Jack’s job as CFO is to develop and implement financial strategies and processes that support company growth and business objectives.

When you boil it down, Jack needs to keep things at Stack on track.

All rhyming aside, keeping things on track is how Trello has become part of Stack’s central nervous system. Jack recently shared his best ideas at a Trello for Teams event in NYC, highlighting their CEO Report board, which can help bring clarity to business objectives and growth goals for all different types of organizations.

Keep It Simple, Keep It Real

When it comes to getting an entire company integrated in Trello, Jack’s top tip is to start simple:

Stack uses Trello to help distribute key information while cutting down on email and preventing unnecessary meetings. However, if you’re just starting to introduce Trello into your organization, Jack cautions against getting too caught up in the bells and whistles: “If you start simple, you’ll have a better chance of succeeding.”

C-Level Clarity

The CEO Report is used at Stack as a type of company overview and prioritization display. At a glance, anyone in the company can see what each team is working on, who is involved at the project level, and how project tasks are being prioritized against other initiatives.

In other words, if you think of Stack Overflow’s Trello activity as a lengthy novel, then the CEO Report would be the front cover.

Now, Jack did say to start simple, and at a glance their CEO Report board might look kind of busy. However, the structure is straightforward: Five lists, with three showing all teams and subteams at the company, and two showing current and completed projects. Teams can submit their weekly updates on their team cards via the comments section, and all past and current projects can be reviewed without having to dig down into project-specific or team boards.

As Jack and his team have ramped up Stack’s growth, this kind of collaborative, transparent organization has become the key to keeping company focus organized.

ceo_view_trello_board.jpgJack advises starting small, then working your way up to a comprehensive Trello board displaying all higher level initiatives across the company.

Customized with Power-Ups and other Trello features, the board is a living and breathing entity for Jack and his team. Here are their favorite three features to use on the CEO Report board:

  • Pirate_Mode_Card_Aging_Screenshot.pngCard Aging: The card aging Power-Up helps team members see cards on a board that haven’t been touched in awhile. When enabled, cards will visibly age with inactivity. There are two modes: “Regular” and “Pirate.” For Jack’s board, Pirate mode is enabled. This makes it so cards will tear, yellow, and crack like an old pirate map.

    It’s fun, but it’s more than that: Jack explained that using this feature helps employees understand what is being actively tackled (lighter in color) versus initiatives that are not top priority at the moment (darker in color). Example_List_with_Card_Aging_Enabled.png

  • Google Drive: This Power-Up allows team members to include only what is absolutely necessary on cards themselves. When an employee looks at the back of a card, they should be able to figure out the overall meaning of initiative or task pretty quickly. Being able to attach additional Google Docs, Sheets, and more, allows for context to be provided without overwhelming the “snapshot” that the cards are meant to provide. Using the Power-Up (instead of attaching documents the old-fashioned way) means their team can access folders and documents in a more streamlined, secure way.
  • Card Cover Images: The cover image feature allows Jack and his team to provide visual cues for what is lying beneath a card. Is it a card about revenue? A chart may be an appropriate cover photo:

    Example_Lists_with_Card_Covers.png

    Trying to update the company on social media channel initiatives? Turns out a cover image may be your best bet to grab eyeballs considering the average attention span is a mere 8.25 seconds.

Start Your Own CEO Report

You can get your whole company on the same page about growth initiatives in a simple way thanks to Jack Sinclair and Stack Overflow. All you have to do is copy this CEO Report sample (with Card Aging enabled) and set it up for your Trello team.

Screenshot_of_SampleCEO_Board.pngCopy Stack Overflow’s CEO Report board here.


“Start as basic as you can so it’s stable,” advises Jack, “and over time you can build in more complexity to your company’s overview framework.” Determine what top-level projects and team details are most useful to keep your company in the loop, and go from there.

Then, use the board as part of your all-company meetings or weekly team check-ins, and you’ll have your company focused on what’s important in no time!

If you like the idea of using more than one Power-Up, than you'll want to check out Trello Business Class.