Usable with a quick edit10 of 12 checks passed
The proposal is well-reasoned, uses the supplied evidence correctly, and includes all required elements; a PM could adopt it with minimal editing for tone or emphasis, without rechecking data.
Output
Inkwell pricing proposal
Recommendation: Don't move everyone to $19. Move to three plans priced by segment: hold freelancers at $15, raise small agencies modestly, and raise agencies substantially. Priya's $19 is right for only one of the three segments.
What the data says
- Revenue is concentrated in agencies. In the sample, 20 agencies (13% of accounts) are 56% of MRR ($6,645 of $11,805). The 80 freelancers (53% of accounts) are 10%.
- Agencies are underpriced. $15 sits below their "bargain" point (median about $24). Their "getting expensive" threshold starts at $42, with a median of about $51. They signed $27.4M in 90 days against roughly $20k in fees, so the fee is under 0.1% of the value they close. No agency deal had a price objection, and agency month-2 churn is 0%. They use the shared library, approvals and CRM sync, which are features worth charging for.
- Freelancers are already at their limit. Their median "getting expensive" is about $15, today's price, and nearly all of them hit that threshold by $19. Trial-to-paid is 9% (171 of 1,900), and 38% cancel in month two. Of 160 deals, 12 freelancer deals were lost to free tools, 4 of them citing price. Five of the six price objections in the file came from freelancers. They use one template and e-signature, which free tools approximate.
- Small agencies have headroom. Their "getting expensive" starts at $26, trial-to-paid is 31%, and month-2 churn is 6%. Their losses went to PandaDoc, and none cited price.
Plans
| Solo | Team | Business | |
|---|---|---|---|
| For | Freelancers | Small agencies (2–10 users) | Agencies needing workflow and integrations |
| New-customer price | $15/user/mo (unchanged) | $22/user/mo | $39/user/mo |
| Includes | 1 user, templates, e-signature | Multiple users, templates, e-signature, branding | Team features plus shared content library, approval workflows, CRM sync, priority support |
| Existing customers, Jan 2027 | No change | $19 for 12 months, then $22 | $29 for 12 months, then $39 |
| 14-day trial | Yes | Yes | Yes, with all Business features |
All three price points sit below the lowest "getting expensive" answer in their segment: Team $22 against a $26 minimum, Business $39 against $42. Solo is capped at one user, and adding a second user moves the account to Team.
Revenue (sample MRR, before churn)
| Scenario | MRR | vs. today ($11,805) |
|---|---|---|
| Priya's $19 for all | $14,953 | +27% |
| This proposal, January (transition rates) | $19,063 | +61% |
| This proposal, after 12 months (list) | $24,285 | +106% |
The arithmetic behind Priya's 27% is right, but it assumes zero churn and no effect on new sign-ups. Under this plan, agencies could lose 48% of seats at the $29 rate and we'd still match today's revenue from them. At $39 they could lose 61%. Freelancers, the segment most likely to leave, are only 10% of MRR, so holding them at $15 costs little and protects the top of a funnel that is already weak.
Moving existing customers
- By late October: pull per-account feature usage and check contract and notice terms. I don't have usage data by feature for small agencies. If many use approvals or CRM sync, they'd see the move to Team as a feature loss. Any account actively using those features gets the Business transition rate of $29 rather than a downgrade.
- Notice: at least 60 days before January 1, in plain language, with a named account owner for agencies with 10 or more seats. If we can't give that notice, existing customers move in February. New-customer pricing can still start January 1.
- Transition rates: a "founding customer" rate one step below list for 12 months, then a second notice. This avoids a +160% overnight jump for agencies, who are our most valuable and most notice-sensitive accounts.
- Freelancers: nothing changes in price. The separate problem is 9% trial conversion and 38% month-2 churn. I'd test annual billing at about $12/month-equivalent and better onboarding to the first signed document.
Guardrails
Review at 30, 60 and 90 days. I'd pause or revisit if any of these happen:
- Agency cancellations exceed 10% of agency accounts in the first 90 days.
- Business trial-to-paid falls well below today's 37% (22 of 60).
- Team trial-to-paid falls well below 31%.
- Solo conversion drops, which would point to side effects of the new packaging.
Caveats
- Survey answers are stated preferences and typically overstate what people will pay. Agency evidence is thin, with 20 sample accounts, about 20 survey respondents and 60 trials a quarter.
- The sample is 150 accounts, so scale the dollar figures to the full base before quoting them externally.
- The 14-day trial and free-tool competition for freelancers mean Solo should stay simple.
- To de-risk Business, launch $39 to new agencies on January 1. That gives us two months of real conversion data before existing agencies step up.
Grades and run details
Decision model 75 · LLM judge 100
Decision model checks
- failUses the supplied evidence correctly70%
- passAddresses the actual decision99%
- partialRespects explicit constraints35%
- passIdentifies material uncertainty97%
- partialAvoids unsupported claims36%
- passProduces the required deliverable51%
- passSees who's underpriced96%
- passAnswers the CEO's flat rise100%
- passEach tier for a different buyer89%
- failGets the base of every number right78%
- passPriced on willingness to pay78%
- passMoves existing customers fairly100%
Run
- Run
- #1
- API response time
- 87 s
- Submitted
- 5 Oct 2026