Most marketing stacks grow organically: one more tool, one more connection, one more workaround. That works fine for a while — until maintenance starts costing more time than the work itself.
The five signs
Someone manually exports data from system A to system B, every single week.
The same customer data gets entered in two places, with room for discrepancies.
A campaign can only go out once one specific colleague has prepared a list.
Nobody dares touch a connection for fear something else will break.
Reports from different systems show different numbers for the same period.
Each of these signs can be patched individually. Together, they signal that the underlying structure is no longer growing with what the team needs.
Where to start
Not with the biggest connection, but with the sign that costs the most time. That's usually also where the biggest risks sit, and where a small intervention becomes noticeable fastest.