Almost every founder we talk to eventually asks some version of the same question. Should we hire a designer, bring in an agency, or find some middle ground between the two? There's no universal answer here. There's only the right answer for where your company happens to be right now, and that changes as you grow. We've worked across all three models, sometimes with the same client at different stages of their journey. Here's what fifteen years of doing this has taught us about when each one actually works, and where founders tend to get it wrong.