Reprice and repackage so your revenue is more predictable.
“Per-seat pricing is capping us. How do I reprice without losing the deals in flight?”
Move off pure per-seat, decide what to meter and what to bundle, set the tiers, and model the impact on deal size and win rate before you change a thing.
What this skill does
Turns "our pricing is leaving money on the table" into a concrete repackaging plan. It finds where your current model breaks (usually a pure per-seat license that bets revenue on headcount), decides what to charge for and what to bundle, sets the tiers and the value metric, and models the effect on deal size, win rate, and free-to-paid conversion before you change a thing. Reprice to de-risk, not just to raise the number.
Inputs
- Works today with: your current price list, your tiers, and a rough read on who buys what. Paste it.
- More powerful with a CRM: it reads real deal sizes, discounting, and win rates by segment.
- Sharper with a product-analytics tool: it sees which features drive value and who is stuck on free.
How it works
- 11. Find where the model breaks
Name what your current model bets on. A pure per-seat license bets revenue on the customer's headcount, so it caps you when they freeze hiring and it under-charges the accounts getting the most value. Say the failure out loud.
- 22. Pick the value metric
Choose what to charge for so the bill grows as the customer succeeds, not as they add chairs. The best metric is one the buyer already believes is fair and can predict.
- 33. Set the tiers and the fences
Decide what is bundled and what is metered, and draw clean fence lines between tiers so a buyer knows exactly why they move up. Bundle the things that drive adoption, meter the things that scale with value.
- 44. Handle the free base
If a large share of active users sit on free, decide what converts them: a usage ceiling, a value-gated feature, or a self-serve motion. Free is a funnel, not a leak, only if there is a path off it.
- 55. Model the impact before you ship
Estimate the effect on average deal size, win rate, and free-to-paid, using your own numbers. A reprice that lifts deal size but tanks win rate is a loss. Reprice to de-risk: bigger deals, held or better win rates, a smaller free base.
Output format
CURRENT: pure per-seat, revenue capped by customer headcount
VALUE METRIC: shift core to seats + a usage tier for the heavy accounts
TIERS: Starter (self-serve) / Team / Business / Enterprise, fences on volume + security
FREE BASE: ~40% on free, add a usage ceiling + one value-gated feature
MODELED IMPACT (from your data, illustrative):
- Average deal size: +25 to 35%
- Win rate: held (value-based framing, not a raw increase)
- Free-to-paid: single digits to low double digits
MIGRATION: grandfather existing seats 12 months, opt-in to new tiers
Tips
- Every projected lift is modeled from your own deal or usage data, or clearly labeled an assumption.
- No move that creates a surprise bill or removes a feature customers depend on.
- The plan states the migration path for existing customers, not just new logos.
- If the change raises deal size but hurts win rate or retention, it does not ship.
Make revenue reporting a weekly habit that drives action.
Pairs a where-we-stand-and-why write-up with a list of hot leads and deals to work now, so the report ends in moves, not a screenshot.
Get one forecast-aware brief that names today's priorities.
Composes deal risk, pipeline, coaching, and conversation reads into a single morning brief, in rep or leader mode.