I've been an account manager at a small ad agency for two years, where I've been managing all client communications and creative feedback. I do enjoy it, but I feel I'm stagnating and ready for a new challenge in media planning. My boss, who is also the agency owner, seems comfortable with me in my current role, though. Should I stick it out a while longer or start looking at ways to move my career in a new direction?

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You could move toward a territory manger where you could have more roles and responsibilities with management role .
You could also try product management role since you already have customer face relationship. You could bring your experience into new products/ product development etc

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