Price and package a product

Recommendation: raise agency pricing, not every user to $19

Launch segmented plans in January 2027. Keep freelancers at $15 per user; price agencies for the collaboration and CRM features they use. Priya’s 27% figure is the gross increase if every account stays: it does not account for cancellations or lost conversions.

Keep the 14-day free trial. Use seat count as the default plan guide, with sales able to recommend the right fit where an account’s needs differ.

Why this structure

• Freelancers show the clearest risk from a blanket increase. In Q3, 9% of freelancer trials became paying customers, versus 31% for small agencies and 37% for larger agencies. Of paying freelancers, 38% cancelled in month two, compared with 6% of small agencies and none of the larger agencies. A higher entry price could compound an already weak conversion and retention picture.
• Survey responses support different price points by segment. Freelancers typically start to feel price pressure around the mid-teens; agencies report much higher thresholds. The proposed $19 Team and $25 Business prices remain well below the survey’s typical “getting expensive” levels for agencies. Treat the survey as directional, not a guarantee of willingness to pay.
• Agency packaging reflects observed value. Agencies use the shared library, approval workflows, and CRM sync; freelancers mostly use one template and e-signature. The Q3 account sample also shows much heavier proposal activity in agencies. Charging more for agency collaboration and integration is more defensible than charging every freelancer more for features they may not use.
• Sales evidence argues against relying on price increases alone. Recorded losses include freelancers choosing free tools and agencies choosing PandaDoc; many no-decisions stayed with their current process. Price objections appear, but are not the dominant story in these records.

Move existing customers carefully

1. New customers: Apply the new plan prices from January 2027.
2. Existing freelancers: Keep them on Solo at $15. Do not force a price increase or a feature downgrade.
3. Existing agencies: Give each account its recommended plan, explain the feature mapping, and grandfather its current access for 12 months. Provide at least 60 days’ notice before any price change; for annual customers, change pricing at renewal, not mid-term.
4. Phase agency increases: Cap each renewal increase at 20%, with a clear schedule to reach the recommended list price within three renewals. Let customers adjust seats or select a lower plan before renewal; do not remove access unexpectedly.
5. Review before scaling: Track trial conversion, second-month cancellations, agency churn, and downgrade requests by segment. Revisit prices after two quarters rather than assuming the sample or survey predicts the full customer base.

The 150-account export is a random sample, not a forecast. The proposed prices are a testable segment-based starting point; blanket repricing would add avoidable freelancer risk.

MEMORANDUM

TO: Priya Nair, CEO FROM: Pricing PM, Inkwell DATE: October 24, 2026 SUBJECT: Q1 2027 Pricing & Packaging Proposal

---

Executive Summary

Your instinct to capture more value is spot on—we haven’t touched price since launch, and our growth gives us pricing power. However, moving everyone to a flat $19/user in January carries hidden risks.

Based on our Van Westendorp pricing survey, win/loss data, and trial cohort metrics, a flat per-user hike across all segments will cause churn spikes among freelancers (whose median "too expensive" threshold is $25/mo) and leave money on the table for larger agencies (who derive immense value from collaboration features and are willing to pay significantly more).

Instead of a blunt instrument, I propose a packaged tier strategy starting January 1st that protects our low-end acquisition funnel, extracts enterprise-grade value from larger agencies, and grandfathering existing customers gracefully.

---

Data Insights & Rationale

1. Willingness to Pay Varies Widely by Segment: * Freelancers ($15 current): Median "too expensive" point is $25–$28. A jump to $19 is survivable, but pushing past $20 risks driving them back to free e-signature tools and Google Docs (our #1 lost-to competitor). * Small Agencies (2–10 seats): Median "too expensive" point is $46–$55 ($15–$18/user effective). They heavily utilize team features (shared libraries, approval workflows). * Agencies (11–50 seats): Median "too expensive" point is $70–$93 ($6–$8/user effective at scale). They view Inkwell as core operations infrastructure and integrate it with their CRM. They are severely under-monitored on a flat per-user model.

2. The Freelancer Churn Trap: Our Q3 trial funnel shows that 38% of freelancers cancel in their second month. Raising their price immediately in January without added value will accelerate this churn.

---

Proposed Pricing & Packaging Structure (Effective January 1)

We will transition from a single monolithic plan to a 3-tier product-led packaging model.

---

Revenue Impact Projections

• Starter Tier ($19 flat): Retains freelancers at your target price point while securing a 26% ARPU lift on single-user accounts.
• Growth & Scale Tiers: By packaging high-value features (CRM sync, approvals) into higher tiers, we capture enterprise willingness-to-pay. For an average 20-seat agency currently paying $300/mo ($15/seat), moving to the Scale tier at $39/seat shifts their MRR to $780—a 160% expansion, rather than a modest 27% bump.

---

Migration & Rollout Plan for Existing Customers

To avoid churn and backlash while hitting our January revenue targets, we will execute the following transition:

1. Grandfathering Window (Peace of Mind): Existing customers will be grandfathered on their current $15/user rate for 90 days (through March 31, 2027), provided they do not change plans. This prevents a sudden holiday-season churn spike. 2. Value-Based Migration (April 1): * Freelancers automatically transition to the Starter plan ($19/mo flat) on April 1, with a 30-day advance notice emphasizing new template updates. * Agencies will be mapped to the Growth or Scale tiers based on their current feature usage (e.g., accounts currently utilizing CRM sync will be slotted into Scale, with a personalized outreach from success reps highlighting the added utility). 3. Opt-Out & Retention Safety Net: Any existing customer who receives the April price change notice will be offered an annual prepayment discount (2 months free) to lock in a intermediate rate, preserving cash flow while securing retention.

Next Steps

With your approval on this structure, product and marketing will finalize the feature gating by November 15, allowing us to build billing migrations and draft customer communications well ahead of the January launch.

Inkwell Pricing and Packaging Proposal

Recommendation

Don't move everyone to a flat $19. Our customers aren't one market.

• Freelancers are 53% of accounts but only 10% of revenue, and they already find $15 expensive.
• Agencies are 13% of accounts and 56% of revenue, and they consider $15 cheap.

A flat $19 overcharges the first group and still undercharges the second. I propose three plans priced by segment, with a staged move for existing customers. Before churn, this delivers about +44% MRR in year one and +95% once fully migrated, compared with +27% for a flat $19.

What the data says

Revenue concentration (150-account sample, $11,805 MRR)

Freelancers are price-sensitive and short-lived. - 50 of 60 freelancer survey respondents put "getting expensive" below $19. For 35 of 60, $15 is already at or past that point. - 5 of the 6 price objections in win/loss came from freelancers. - Freelancers lose to "Google Docs and a free e-signature tool" (12 of 70 deals), not to PandaDoc. - Their trial conversion is 9%, and 38% cancel in month two. - No freelancer in the sample has been a customer longer than 9 months. - They mostly use one template and e-signature.

Agencies are underpriced. - Every agency respondent's "bargain" price is $20 or higher. - 7 of 20 put "too cheap to trust" at $14–15. - Agencies never raised price in win/loss. Their losses to PandaDoc were about product. - They had 0% early churn and use the features freelancers don't: shared library, approvals and CRM sync. - At $35, every sampled agency would pay under 0.5% of the contract value it signs through Inkwell.

Small agencies have room. - Every respondent's "getting expensive" point is $26 or higher. - Trial conversion is 31%, with 6% early churn.

Plans

The 14-day free trial stays on all plans.

Why these prices: - $12 Solo sits below "getting expensive" for 56 of 60 freelancers. It costs about 2% of total MRR to cut existing freelancers from $15. - $25 Team is below every small-agency respondent's "getting expensive" point. - $35 Agency is below every agency respondent's "getting expensive" point (lowest is $42) and well under "too expensive" (lowest is $60).

Plan fences: - The seat cap (Solo = 1, Team ≤ 10) is the main fence. It maps onto the segments the data already uses. - Agency features are deliberately the ones a larger team needs to manage people, not new product promises.

Moving existing customers

How to run it: - Notice. Give at least 60 days' notice to anyone whose price rises. If January is closer than that, launch new prices for new customers in January and move existing customers in February or March. - Lead with what's included. Existing teams keep every feature they use today. The message is "you're on the plan built for teams," not "the price went up." - Annual lock. Offer annual prepay at the year-1 rate, locked for 12 months. This converts the increase into commitment. - At-risk agencies. Have someone call the top agencies by MRR personally before the email goes out. - Your $19 still appears. It becomes the year-1 rate for existing small agencies.

Revenue impact (sample MRR, before churn)

What this means: - The flat $19 figure assumes zero churn and no drag on new sales. Most of the churn risk sits with freelancers, the segment that pays the least. - Year 1 beats flat $19 unless we lose about 12% of MRR. That's roughly 1 in 5 agency seats, in a segment with 0% early churn and no price objections. - The real risk is concentrated. Agency seats carry most of the upside, so agency retention through migration is the thing to watch. Freelancer churn barely moves the total.

Risks and checks before announcing

1. The survey is stated willingness to pay, not behaviour. We don't know whether respondents are customers or prospects. To limit the risk: - Launch new-customer prices first and watch trial conversion by segment for 4–6 weeks before existing customers move. - Keep the agency year-1 rate at $25. 2. Check CRM sync usage before finalising Team. CRM sync is in Team so small agencies lose nothing. If heavy CRM-sync users are mostly 11+ seat accounts, it could move to Agency instead. I need feature usage by account size to confirm. 3. Agencies near the 10/11 seat boundary may resist the jump. Allow a 12-seat grace period on Team for existing customers in year 1. 4. Freelancer losses to free tools aren't solved by a cheaper Solo plan alone. A free tier (e.g., 2 sends a month) is worth testing separately on new trials. It isn't part of this launch because it could cannibalise paying freelancers, who send about 3 proposals a month. 5. Metrics to track monthly: - Trial-to-paid conversion by plan - Month-two cancellations for Solo - Agency logo and seat churn through each migration step - Win rate against PandaDoc

Decision needed from Priya: approve the three plans and the staged migration, and confirm the existing-customer timing (January if 60 days' notice is possible, otherwise February/March).