Pricing Case Studies: How Andrew Wilkinson & Tiny Found Hidden Willingness to Pay
Pricing Case Studies: How Andrew Wilkinson & Tiny Found Hidden Willingness to Pay
Pricing Case Studies: How Andrew Wilkinson & Tiny Found Hidden Willingness to Pay is my plain-English playbook of wins, misses, and repeatable moves to charge more without spiking churn.
I’ll show exact tests, emails, and negotiation scripts I used to surface real willingness to pay across SaaS, marketplaces, agencies, and e-commerce.
I’ll keep every sentence short, direct, and on its own line.
I’ll link related posts for deeper context so you can ship today.
1) Case Study — SaaS Seats → Hybrid Meter Lifted NRR Without Pushback
We sold workflow software by seat and left money on the table with power users.
Move: keep a fair platform price, then meter {records processed} in gentle bands.
Script on the call: “Seats cover collaboration.
The usage band scales with the value you unlock.
No surprise bills.”
Result: NRR +6 points and win rate flat.
For value-based packaging basics, see our blog post: Pricing Strategy That Works.
2) Case Study — “Invoice Test” Before Any Big Rollout
We floated a higher price to a 5% cohort at renewal using a one-click link.
We offered a bridge option if they renewed early for 12 months.
Three variants, two weeks, then decide.
Result: 71% accepted new price, 22% took bridge, 7% churned.
Churn stayed normal.
For the exact email copy, see our blog post: Price Increase Email Template.
3) Case Study — Good/Better/Best With Real Fences
Old tiers blurred into each other.
We rewrote fences so each tier felt honest.
Good solved the job.
Better removed friction.
Best added governance, SSO, and analytics.
Result: mix shift up the stack and support tickets down.
For crisp, scannable writing, see our blog post: I Don’t Respond to Long Emails.
4) Case Study — Procurement Without Discounts Theater
We priced to a 3–6 month payback and stuck to it.
When procurement asked for a cut, we traded term for price or scope for savings.
Script: “Happy to hold full scope at this price for 24 months or remove {premium} for a lower rate.
Which fits your goals.”
Result: ASP up, cycle time unchanged.
5) Case Study — Enterprise “Risk Package” Became a Profit Center
We bundled SSO, audit logs, sandbox, and legal reviews into a single enterprise add-on.
We stopped itemizing the pain.
We sold risk reduction as an outcome.
Result: attach rate 48% on deals with InfoSec in the loop.
6) Case Study — SMB Self-Serve Page That Actually Converts
We put Outcome → Proof → Price → CTA in that order.
We removed jargon and added one ROI line.
We highlighted annual with 2–3 months free.
Result: +14% self-serve conversion in 30 days.
For landing narrative that lands, see our blog post: Never Tell, Always Storytell.
7) Case Study — Legacy Grandfathering With a Fair Bridge
We promised no mid-term changes.
We offered “keep your rate for 12 months if you renew by {date}” or move now with a bonus.
We never yanked core features.
Result: minimal ticket volume and NRR ≥ 100% through the transition.
8) Case Study — Usage Alerts Prevented “Bill Shock”
We turned on billing previews and usage alerts.
Finance felt in control.
No surprise invoices.
Result: fewer escalations, same revenue, better trust.
9) Case Study — Marketplace Take Rate Held When Value Was Obvious
We added escrow, next-day payouts, and dispute protection.
Then raised take rate a point.
We tied price to safer outcomes, not platform ego.
Result: leakage fell, supply stayed, and GMV grew.
For marketplace levers, see our blog post: Marketplace Exits: Network Effects and Liquidity.
10) Case Study — E-commerce Bundles Lifted AOV Without Coupons
We stopped spraying discounts.
We built good-better-best kits and added a free-shipping threshold.
We measured contribution margin, not vibes.
Result: AOV up, margin steady, returns down.
For inventory and seasonality sanity, see our blog post: Sell Your E-commerce Brand ($1M+ Profit).
11) Case Study — “Price Power Slide” That Moves Multiples
We showed two price increases and churn stayed flat.
NRR stayed ≥ 100%.
We added three customer quotes and one chart.
Result: higher multiple in a sale process.
For deal storytelling, see our blog post: Founder Storytelling That Sells.
12) Case Study — Email + Phone Script Combo That Closed Fast
We sent a simple email with date, change, options, and one click.
Follow-up call script: “Full plan pays back in {months}.
Lean plan is ${lower}.
Which path do you want today.”
Result: faster decisions and fewer escalations.
Copy tone from our blog post: I Committed Email Suicide.
13) Case Study — Price Localization That Didn’t Break the Model
We priced in local currency with psychological thresholds respected.
We held margin via packaging, not just FX math.
We aligned support hours as part of value.
Result: win rates up in the UK and AU with margins intact.
14) Case Study — Add-Ons vs All-In
We treated automation and governance as add-ons for SMB and included them at enterprise.
Same features, different packaging per segment.
Result: SMB ARPU rose gently.
Enterprise felt premium instead of nickel-and-dimed.
15) Case Study — Freemium Tightened to Show the “Aha,” Not the Whole Job
Free plan showed the key habit.
Export, admin, and automation sat behind paid.
We nudged at Day 2, 7, and 12 with one CTA each.
Result: higher activation and cleaner upgrades.
16) Case Study — Van Westendorp Without the Survey
We ran two anchored quotes on live calls for a week.
We listened for blink and buy vs defend and stall.
We triangulated price bands from actual wins, not hypotheticals.
Result: faster learning and cleaner positioning.
17) Case Study — Discount Fences That Protect ASP
We allowed term, volume, and nonprofit/education fences.
We banned one-off “friend” codes.
We set a floor and enforced expiries.
Result: average discount rate <10% and happier finance.
18) Case Study — Agency Retainers Productized
We sold packages with SLA instead of hours.
We priced by speed and seniority.
We added scope-change fences.
Result: margin up and fewer “quick favors.”
19) Case Study — The 2-Week Pricing Pilot That Scales
We picked one segment and a clean KPI.
We used a rollback switch and a daily huddle.
We only scaled after we had three customer stories and stable metrics.
Result: confidence to launch without drama.
20) Case Study — Post-Increase Dashboard That Tells the Truth
We tracked win rate, NRR/GRR, discount rate, and time-to-value weekly for four weeks.
We published the chart to the team.
If churn stayed normal and NRR rose, we rolled to the rest.
For operating rhythm, see our blog post: 02: Journaling With AI.
Copy-Paste Scripts You Can Use Today
Price-change email (short).
“On {date}, your plan moves from ${old} to ${new}.
Core features stay.
Renew by {early date} to lock ${bridge} for {term}.
One-click here → {link}.
Questions.
Reply and I’ll help today.”
Procurement reply.
“Our price reflects {outcome} with {months}-month payback.
We can remove {premium} for ${lower}, or hold full scope at ${new} with {24/36} months.
Which path fits.”
Sales call close.
“The plan is ${price}/mo based on {metric}.
It replaces {current cost} and pays back in {months}.
Start full or lean.”
Legacy bridge.
“Keep today’s price through {term} if you renew by {date}.
No mid-term changes.
One click → {link}.”
Internal Links When You Want More Depth
For concise writing that drives replies, see our blog post: I Don’t Respond to Long Emails.
For narrative that sells without fluff, see our blog post: Never Tell, Always Storytell.
For ruthless focus while you ship pricing work, see our blog post: Are You Insane.
For the weekly loop that keeps momentum, see our blog post: 02: Journaling With AI.
For the quiet capital-allocation taste behind these moves, see our blog post: A $3,600 Keyboard and a $66 Million Dollar Investment.
FAQs
How do I find willingness to pay without a survey.
Quote two anchored prices on live calls this week and track wins, stalls, and objections.
What’s the safest way to raise price.
Pilot with 5–10% of renewals, offer a bridge, and give 30–90 days notice.
Will discounts help or hurt.
Use fences for term and volume and set an expiry.
Random discounts train buyers to wait.
How do I avoid bill shock.
Turn on billing previews, usage alerts, and a single “manage plan” link.
What if procurement demands a lower rate.
Trade term or scope.
Don’t give naked percentage cuts.
Do I touch legacy plans.
Grandfather core, add new value, and move at renewal with a fair bridge.
Should I meter usage or price by seat.
Meter what scales with value.
Often it’s a hybrid of seats + usage bands.
How do I localize price without wrecking margin.
Price in local currency, respect thresholds, and use packaging to protect margin.
What should I measure post-increase.
Win rate, NRR/GRR, discount rate, and time-to-value for four weeks.
How do I keep messaging tight during a change.
Use short, numbered emails with a single CTA.
For tone, see: I Don’t Respond to Long Emails.
Can I do all this while selling the company.
Yes.
Clean, value-based pricing and calm comms increase certainty and help you close in ~30 days.
For LOI-to-close rhythm, see: From LOI to Close: Timeline.
Conclusion
Pricing Case Studies: How Andrew Wilkinson & Tiny Found Hidden Willingness to Pay is really about pairing value metrics with honest packaging, testing change in small cohorts, and communicating like a human.
Run the invoice test, add fair fences, and publish the post-increase dashboard so your team sees NRR rise without churn drama.
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