Price and package a product

To: Priya Nair, CEO From: PM, Pricing Subject: January Pricing & Packaging Proposal: Tiered Plans vs. Flat $19 Increase

Executive Summary

Moving to a flat $19/user/month will hurt our freelancer acquisition while leaving massive agency revenue on the table. Instead of a flat increase, we should launch a three-tier packaging model ($12 / $29 / $49) gated by team size and agency workflows. By aligning price with value, we can increase MRR across our existing base by ~96% (vs. <27% under the $19 plan) while improving top-of-funnel conversion.

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Why a Flat $19/Seat Doesn't Fit Our Data

1. Agencies drive 90% of our revenue and are severely underpriced. In our 150-account sample ($11,835 total MRR): * Freelancers are 54% of accounts (81) but only 10.3% of MRR ($1,215). They send ~8 proposals/quarter (~$5.6k signed value) and stay on average 5 months. * Small Agencies (2–10 seats) are 33% of accounts (49) and 35.4% of MRR ($4,185), averaging $129k in signed value/quarter and 17.5 months tenure. * Mid-sized Agencies (11–50 seats) are 13% of accounts (20) but 54.4% of MRR ($6,435), averaging $1.4M in signed value/quarter and 16.5 months tenure.

2. $19 breaks Freelancer willingness to pay (WTP), but is a giveaway to Agencies. * Freelancers: Our Van Westendorp survey shows $15 is already the median "getting expensive" threshold for freelancers. At $19, 83% of freelancers view Inkwell as getting expensive, and 15% consider it "too expensive" to buy. Furthermore, Q3 funnel data shows freelancers convert at just 9% and 38% churn in month 2. When we lose them, it’s to "Google Docs + free e-signature"—and 80% of all price objections in our win/loss data come from freelancers. * Small Agencies: Median "bargain" is $15; "getting expensive" is $32; "too expensive" is $50. * Agencies (11–50): Median "too cheap to trust" is $12 (and $14–$15 for a third of respondents!). At $15, we look dangerously cheap to larger teams. Their median "bargain" is $25, and "getting expensive" is $51. We only lose agencies to PandaDoc—with zero price objections.

3. Feature usage naturally separates segments. Freelancers only use 1 template and e-signatures. Agencies rely heavily on the shared content library, approval workflows, and CRM sync.

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Proposed Pricing & Packaging

We should replace the single $15 plan with a Free Trial + Freemium/Low-Floor entry for freelancers, and two value-priced tiers for agencies:

Note: All paid tiers retain the 14-day free trial.

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Why This Works

• Fixes the Freelancer Funnel (Free & Solo at $12): Lowering the solo price to $12 (below the $15 "getting expensive" mark) reduces month-2 churn. The Free tier (1 template, 2 proposals/mo) captures the 91% of trialists who don't convert and neutralizes the "Google Docs + free e-sig" threat, keeping low-volume freelancers in our ecosystem until their deal flow picks up.
• Captures Agency Value ($29 and $49): $29/user for Small Agencies sits safely below their $32 "getting expensive" threshold while nearly doubling ARPU. $49/user for 11–50 Agencies sits below their $51 threshold, eliminates the "too cheap to trust" signal, and funds enterprise-grade features to beat PandaDoc.

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Existing Customer Migration Plan

1. January 1: Launch new pricing for all new signups. 2. Freelancers (1 seat): Automatically move existing $15/mo freelancers to the $12/mo Solo plan in January. Framing a pricing update as a price cut for our largest user group by headcount will generate massive goodwill and social proof, while only costing $243/mo across the sample (2% of MRR). 3. Agencies (2+ seats) — 90-Day Grandfathering + Annual Lock-In: * Give existing agencies 90 days' notice (effective April 1) before migrating them to Team ($29) or Agency ($49) based on their seat count and feature usage (e.g., accounts using approval workflows move to Agency). * The "Loyalty Bridge": Offer existing agencies the ability to lock in a legacy annual rate ($19/user/mo for Team, $29/user/mo for Agency) for 12 months if they switch to annual billing before March 31. This minimizes churn, pulls cash forward, and still beats your $19 target.

Revenue Impact (on the 150-account sample)

• Current MRR: $11,835
• Priya’s $19 Flat Plan: $14,991 (+27% before heavy freelancer churn; likely ~18–20% net).
• Proposed Tiered Model (at list price): $23,190 (+96% MRR)—broken down into $972 from Freelancers, $8,091 from Small Agencies, and $14,127 from 11–50 Agencies. Even with 50% of agencies taking the discounted annual Loyalty Bridge in Year 1, net ARR grows by >60% with near-zero logo churn.

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).

Inkwell pricing and packaging proposal

To: Priya Nair | Decision: segmented pricing, not $19 for everyone

Recommendation

Launch three feature-based plans for new customers in January. Keep the freelancer entry price at $15; charge more for agency collaboration and integration. Move existing agency customers gradually, preserving their current functionality.

A blanket $19 increase produces 26.7% more revenue only if paid seats remain unchanged. Losing 21.1% of paid seats would erase that uplift. It also raises prices for our most fragile segment while leaving agency willingness to pay underused.

What the evidence says

• Revenue is concentrated in agencies. The random sample contains 80 freelancers, 50 small agencies and 20 larger agencies. Its 787 seats generate $11,805 MRR; agencies contribute 89.8% of MRR, despite representing only 46.7% of accounts.
• Freelancer acquisition and retention are weak. Trial conversion is 9%, versus 31% for small agencies and 36.7% for larger agencies. Second-month cancellation is 38%, 6% and 0%, respectively. The last figure comes from only 22 conversions.
• Price tolerance differs substantially. Survey “getting expensive” thresholds range from $12–20 for freelancers, $26–42 for small agencies and $42–67 for larger agencies. These are stated preferences, not proven demand curves; one larger-agency response has inconsistent thresholds.
• Value and usage differ. Freelancers sent 3–12 proposals over 90 days, versus 18–63 for small agencies and 95–287 for larger agencies. Agency usage emphasizes the shared library, approvals and CRM sync; freelancers mostly use one template and e-signature.
• Cheap substitutes matter. All 12 freelancer losses went to Google Docs plus free e-signature; four explicitly cited price. Agency losses went to PandaDoc, without recorded price objections. That does not establish why they lost—or prove agencies will accept any increase.

Proposed plans

Prices are USD, billed monthly. Retain the 14-day trial. Defer annual discounts until monthly pricing is validated.

Team and Business have no minimum seat commitment or segment-based eligibility. A two-person agency can buy Business; a larger agency can buy Team. Charge for users who create, edit or approve proposals—not external recipients signing them.

Do not introduce proposal limits, signature fees or charges tied to contract value. They would discourage the activity that demonstrates value. Signed contract value is context, not revenue attributable to Inkwell.

These prices are testable starting points, not survey-derived optima. Business’s incremental value must justify its premium; validate CRM demand before treating larger agencies as automatic Business buyers.

Moving existing customers

1. Give at least 90 days’ notice, stating the customer’s current bill, transition bill, eventual price and effective dates. If notice cannot be delivered in time, January is new-customer launch only.
2. Existing freelancers remain at $15. Preserve all functionality already included; offer Team or Business upgrades voluntarily.
3. Existing agencies move first to $19/user, at the first eligible renewal after notice, for six months. Then move to Team at $29, or Business at $39 if affirmatively selected.
4. Preserve existing feature entitlements, including CRM sync, on migrated Team accounts. Do not remove functionality to manufacture an upgrade. Business packaging applies cleanly to new accounts; legacy exceptions are explicit.
5. Honor contractual commitments. Offer cancellation and data export before increases, plus a documented, time-limited hardship extension. Avoid permanent discretionary discounts.

Revenue expectations and validation

At unchanged seats, the sample would generate:

• Blanket $19: $14,953 MRR, +26.7%.
• Agency transition at $19; freelancers unchanged: $14,633, +24.0%.
• All agency seats eventually on Team: $21,703, +83.8%.
• Small agencies on Team; larger agencies on Business: $26,133, +121.4%.

The last two are allocation scenarios, not forecasts: feature needs, downgrades, seat reductions and churn are unknown. Do not multiply sample totals into company revenue without the full account count and portfolio validation.

Before announcing final prices, interview customers across segments and test the proposed packages against today’s offer with new trials. Track conversion, second-month retention, revenue per trial, paid-seat contraction and support complaints by segment. Use a staged existing-customer rollout with a comparable holdout; pause expansion if incremental revenue after churn and seat contraction is non-positive.

CEO message: “We’re keeping an accessible solo plan and introducing agency plans priced around collaboration and integration—with advance notice and a gradual transition for existing customers.”