Doing the work

How do I run an upsell conversation without sounding like I am shaking them down?

The short answer

Earn it first. If you cannot show the customer a result they got in the last quarter, you have not bought the right to ask for more money, and they can feel that. When you can, frame the upsell as the next problem rather than the next tier: here is what you achieved, here is the thing blocking you from doing it for the rest of the team, here is what that costs. Bring the new stakeholder into the conversation early instead of asking your champion to sell internally alone. And be willing to say not yet, because one badly timed ask costs you more than the deal was worth.

Go deeper, your way

5 hand-picked resources, 5 link-checked. Pick how you want to dig in.

The same ground, at another level

How expansion, upsell and churn reads from a different seat.

People also ask

What is net revenue retention and why does every investor keep asking me for it? NRR is what happens to the revenue from one group of customers over a year, with no new logos counted: start with what they paid, subtract what chu... Breaking into GTM 4 resources → What is the difference between gross retention and net retention, and which one should I watch? Gross retention counts only what you lost: churn and downgrades, capped at 100 percent. Net retention adds expansion on top, so it can go above 100... Breaking into GTM 5 resources → What does land and expand mean, and does it apply to my company? Land and expand means you deliberately sell a small first deal to one team, prove it works, and grow from there into more seats, more teams or more... Breaking into GTM 5 resources → How much churn is normal, and is mine bad? For software, annual churn above roughly 6 percent is the point where people start calling it high, and monthly churn benchmarks vary hugely by who... Breaking into GTM 4 resources → How do I spot which accounts are actually ready to expand? Look for accounts that are pressing against a limit and accounts that are spreading sideways. Hitting a usage ceiling, adding users faster than the... Doing the work 4 resources → How do I work out why customers are actually churning instead of guessing? Three passes. First, cohort the churn: group customers by when they signed up and by what they did, then see whether people leave at month three or... Doing the work 4 resources →

Also in Starting Up

The same ground, over in Grow & market, our Starting Up track.

Also in D2C

The same ground, over in Grow organically & retain, our D2C track.

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