Seat & Feature-Adoption Upsell Playbook 2026

Build the benchmark once per add-on, and once for seats. Refresh it quarterly:

1. Comparison customers: accounts on the same plan tier that bought the add-on, or added seats, in the last 18 months (default) and still use what they bought – active in it in the last 30 days. Aim for 20; with fewer, label it low confidence.
2. Their eight weeks before buying: weekly use of the feature the add-on extends (or hits against its limit), the number of power users – default, three or more days a week in that feature – and active users against seats paid.
3. The pattern: the median of each, and the median price of what they added. Your CS lead or head of sales approves it.

Each week, compare each account in the segment that doesn't own the add-on: feature use against the buyers, active users against seats paid, ARR against peers, and signs of a workaround (exports to a spreadsheet, a limit hit and retried, a support ticket about doing it by hand). The gap value is the add-on's price, or extra seats times your seat price. Say an account pays $20,000 a year and uses reporting the way buyers did, and the reporting add-on is $4,000: the $4,000 is a comparison, not a forecast. (The numbers are illustrative.)

Run it as a weekly saved query in PostHog, Amplitude or Mixpanel, or a spreadsheet. Under about a hundred accounts, do it by hand.

• Sustained four weeks? Default, at the buyers' level in four of the last six weeks. A migration or a month-end spike isn't a gap.
• Already paid for? Check the contract in billing or the CRM. If it's covered, the job is adoption, not new revenue – the second-value play.
• Renewal, cuts & tickets: renewal date and stage, plus 90 days of CRM notes and support tickets.
• Named power users: who uses the feature most, and who invited them. Record it now.

Leave it alone if any of these hold (defaults): usage didn't hold, it's already paid for, renewal is inside 60 days (the gap goes into the renewal conversation instead), there was a cut or open escalation in the last 90 days, or the gap value is below the smallest deal your team opens. Everything else picks a move.

Set Recommended move to No move, write the reason in one line, and set Review date to when it could change. A pitch on a spike that fades teaches the customer to ignore the next one. The leave-it-alone play covers the call in full.

• Add-on: feature use at the buyers' level, the add-on not on the contract, and a named power user.
• Seats: active users over seats paid, four of the last six weeks, by the seat buyers' median margin – default until you have it, 10% or three seats, whichever is more.

Both? True-up first; note the add-on for the next check. One ask at a time.

A deal in your expansion pipeline, first stage: the add-on named, the gap value as the amount, the power users associated, and the deal note below.

The true-up note below, for the next account review or renewal touch. Usage already passed the contract; the conversation is about making the paperwork match, with the user list on the table.

The AM or AE reads the evidence and runs it as drafted, changes it, or passes. For an add-on, book the power users, not procurement, and show it on their own data: the part of their week it takes off. Before acting, record the success measure and the review date: the add-on in use in four weeks is progress; a paid add-on or true-up within a quarter is the result. Once a lane's drafts have been right for a few weeks, your team can choose to automate it.

On the review date, record three answers: did they buy, do they use it, and what else played a part? If nothing moved, change the move, stop it, or give it time. Each quarter, add new buyers to the benchmark and drop add-ons nobody uses. If accounts keep reaching the buyers' level and not buying, tell whoever sets pricing.