I have this nagging feeling we have an obvious upsell opportunity right in front of us, but the whole team is blind to it.

Our retention is solid and users keep asking for specific features in support tickets.

But when I bring up potential upsells in team meetings, everyone just talks about acquisition instead.

Feels like we’re leaving money on the table.

Grab your support tickets and see what features people keep asking for - that’s your roadmap. Make the most popular requests into paid tiers. Your users are basically telling you what they’ll buy. Pick one feature, put it behind a paywall, and test pricing with your best users first. Don’t waste time debating - let the numbers show if the upsell actually works.

Support tickets are basically free market research. If users keep asking for the same stuff, that’s your upsell right there.

Focus on existing users first. They drive steady revenue.