Beyond “Checkbox” Integrations: Ensuring Seamless Creative Operations

The world is full of technology tools, with more launching every day. Although many of us would like just one system or tool to rule them all, the future of creative operations looks like a technology “stack.” Many tools, each acting as a System of Record for some of the steps in the content journey.

System integration is certainly a critical element in this new world of many interdependent tools. Thankfully, many technology vendors now offer “out of the box” integrations with other systems. This can be a tempting way to develop your short list of potential solutions — just pick the tools with the most integrations to your other systems and discard the rest! Although this approach is tempting, it can also lead to very poor outcomes.

That’s because technology vendors understand how organizations buy, so they fill in as many integration checkboxes as possible to ensure their solution makes that all-important short list. However, many of these integrations are truly built to “check the box,” rather than solve real user problems.


We fell into this trap TWICE in our own business, despite that we develop software and thought ourselves pretty savvy when it comes to picking software tools.

The first time, we purchased a CRM that promised to integrate to our Accounting system, so our sales reps could convert a sales order directly into an invoice (eliminating dual entry), and have visibility to which clients had paid. But alas, once we started using the CRM, we discovered the integration was, quite simply, crap. It worked ok for some accounts, but for our largest clients, it would fail to show any of their accounting data, just a cryptic error. After a series of tech support exchanges in which the software vendor seemed mystified, we actually figured out the root cause ourselves– if the account had over a certain number of contacts in the CRM, the Accounting integration would break, because it was written in such a stupid way. We logged the bug with the vendor, but it still wasn’t fixed 18 months later when we decided (based on a lot of reasons, including their crappy integrations), that it was time to switch CRMs.

This time, we knew we were ready! Once we had a short list of CRMs, we set up a trial period so we could test the Accounting integration ourselves, since we knew a demo alone wouldn’t necessarily reveal its true nature. Our favorite candidate CRM’s Accounting integration was exactly what we wanted, and displayed none of the wonkiness of our prior CRM. We were sold, and made the big switch! …And soon discovered a new twist. The integration was perfect — but it was only available for a single user in the CRM system! So instead of our whole sales and account management teams having visibility, we had to pick a single user to get all those benefits, while everyone else “flew blind.” The CRM vendor claimed the limitation was actually on the Accounting software side, so there was nothing they could do about it. The Accounting system vendor barely acknowledges we exist, so no luck so far figuring out if that is even true.


So what’s the moral of the story? Modern technology systems are very complex. Consequently, integrations between them are even more complex. Because integrations must convert the internal language of one system to the internal language of the other, like translating Chinese to French. A real expert might be able to do it, but it’s not just flipping a switch. And if you really want the translation to be accurate, don’t trust the generic Google Translate interpretation.

In addition, your organization is likely changing out your Marketing tech regularly over a period of years, so the specific systems you want to integrate between may change as well. So tools with a more configurable and flexible integration approach are likely to be more useful over time than “hard coded” integrations that may not work the way you want, or quickly become irrelevant when IT rolls out the next new system.

So when it comes to integrations, dive deeper and get your technology team engaged with the vendor before you buy, to really understand the business needs and whether their integration offering can stand the heat in the creative operations kitchen.


  • System integrations can be done poorly or done well, and sometimes it’s hard to tell the difference without a deep dive
  • It’s critical to understand the User Stories that an integration serves in order to evaluate if it will work for your teams
  • Technology moves fast and poorly designed integrations can break or become obsolete if they aren’t maintained by system vendors