The expansion motion that doesn't feel pushy
Selling more to an existing customer is the easiest revenue you'll ever make — if you do it right. Most teams turn it into the worst kind of pressure.
Expansion revenue is the holy grail — high margin, low CAC, fast cycles. It also tempts every sales team to push too hard, too soon, on customers who haven't even succeeded with what they originally bought.
The earned expansion
Wait until the customer is winning with the original purchase. Notice the moment they start asking for things adjacent to the product. That's the natural opening. Anything earlier feels like the salesperson showing up at their dinner.
What to actually say
Not "we have a new tier." Try "we noticed you've started doing X — here's something that would make X work better." Be specific. Tie it to evidence of their behavior. Make it about their outcome, not your number.
The best expansion conversation is the one the customer brings up. Your job is to be paying attention when they do.