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Slack is an indispensable tool at Sterling & Stone. 

“Isn’t it just like texting?” Johnny asked a decade ago, when we first started using the app. 

Only if texting had a photographic memory, and a secret lair filled with powerful features, plus integrations that can transform the way a team works together. 

And that’s the free version. 

For companies with more complex needs, like ours, paid Slack moves the app from being an extremely valuable tool to an invaluable one.We used basic Slack for seven long years before finally experiencing the Shangri-La of the pro version, despite my dying to upgrade for the entirety of that era. 

This lingering wait came for two reasons: Slack’s business model is a bit of evil genius bullshit, and an internal culture clash with our former CFO kept S&S from growing for far too long. 

The Slack business model is simple. Their app will blow you the fuck away with its free version, stacked with basic features that facilitate fluid team communication. 

But as your team grows and expands, along with the needs of your business, you start bumping up against some serious limitations. 

Message Archive Limitations: The free version of Slack has limited message history storage, making it impossible to access conversations older than 90 days. This is a problem considering our projects are always discussed in Slack (it’s the only place we all talk, essentially serving as our office space) and questions about the beginning of an endeavor often arrive at the end. I can’t count the number of times I tried to reference something that had already disappeared, but those frustrating experiences totaled in the hundreds at least.

File Storage Restrictions: Limited file storage on a free account is fair, but when we’re constantly sharing book covers and other media, that space goes fast. We were constantly using a web app called Slack Deletron, alerting the entire studio that it was time to go through and delete anything we no longer needed in Slack. So, inefficiencies all around. 

Limited Search Functionality: Advanced search features are restricted in free Slack, making it harder to efficiently locate specific information within a large volume of messages. But specific information is the only kind we’re ever looking for, and a large volume of messages is par for the course, so searching was a constant and heavy expense on our time. 

There are many other features that make paid Slack worth every dollar, like integrations that I never personally accessed, but people who are smarter than me about that crap in our company absolutely do, and the entire system is stronger for it. 

The problem with paid Slack is that it goes from totally free to rather expensive. With our 40+ storytellers in-house, basic Slack where we can all still fluidly communicate with each other is completely free, but upgrading bumps us up to just under $500 per month. That’s a big difference. 

The genius of this model is that it scales with your business. The more your team relies on Slack, the more value you get from the paid plans. And once you’ve experienced the power of paid Slack, it’s awfully hard to go back. 

The app could quadruple its cost and it would still be a non-negotiable expense for us, though please don’t tell the fine folks at Salesforce I said that. 

So, we’ve covered the model’s evil genius, what was that about the culture clash? 

Johnny always had a hard time seeing the value of paid Slack, because despite being our COO for several years, he never spent any time in the S&S weeds. The only feature Johnny ever used was the instant messaging that made it seem just like texting. Sure, hopping on Deletron every couple of weeks was annoying, but definitely better than going from free to several hundred dollars a month. 

I could have won Johnny over, but our Chief Financial Officer at the time was a hard no on Slack, flat out refusing to greenlight our use of the tool, even when the lack of a pro plan was costing us thousands in lost time and productivity. Not to mention all that stilted growth. 

Having a CFO who only saw the numbers in black and white had been casting a pall across our studio for a while. Sterling & Stone will always be a company that takes chances and invests in its future. We have no office space or utilities, so our overall overhead is light. Paid Slack was clearly a baseline need, and nurturing a growing company’s finances is about much more than how much money it keeps in the bank. 

Fear-based accounting was the number one impediment to our growth until we finally corrected the problem. We started using paid Slack immediately following our former CFO’s departure. Our studio has run smoother every day since, thanks to that decision. 

We have boosted our productivity many times over and the people who have the most valuable time can now leverage it better. Everyone in the studio benefits. 

Our entire team can now access the full history of conversations, making it easy to refer back to important discussions and decisions. We can store and share files without worrying about running out of space. And our advanced search capabilities make it a breeze to find the information we need, when we need it.

In the years since, #paidslack has become part of the Sterling & Stone lexicon

Our former CFO refused to green light paid Slack because they did not see the value. Ten minutes after they were no longer with us, Niamh and Sean signed up for the pro plan, use it every goddamned day, and have now made #paidslack shorthand to represent shortsighted or penny pinching behavior.

#paidslack is a reminder that tripping over dollars to pick up pennies might save you a few bucks in the short term, but it can cost you dearly in the long run. Create a culture of trust, empowerment, and shared purpose, there’s no limit to what you can achieve.