How do I upsell without it feeling like a money grab?

You do upsell, but you wrestle with when to do it and how to make it feel like genuine help rather than a reach for more money. That discomfort is a good sign. It means you actually care whether you are serving the customer. The people who never feel it are the ones who come across as grabby. The answer is to root the upsell in the customer's situation, not your target. An upsell feels like a grab when it serves you first. It feels like value when it clearly solves a problem the customer already has. So the timing follows the need: you offer more when they have reached a point where more would genuinely help them. Before your next upsell, ask yourself one question: would I recommend this even if it did not benefit me. If yes, say it plainly and tie it to their specific situation. If you hesitate, wait. That honest test keeps you on the right side of the line, and customers can feel which side you are on.