I pay $100/month for Claude Max. It’s the single most important tool I use every day. I’ve built 10+ production apps on it. I run my entire business through it. I’d pay double.
And yet — right there in my billing settings — there’s a simple “Cancel plan” button. No phone call. No email to an account executive. No 30-day written notice requirement. No guilt trip. No “are you sure?” gauntlet with 14 steps. Just… cancel.
Here’s what that looks like:
Settings → Billing → Cancel plan. Done.
Meanwhile, Anthropic just confirmed it crossed $14 billion in annualized revenue at the February of 2026 — up from $1 billion at the start of 2025. That’s 14x growth in 14 months. .
This is, by any measure, the fastest-growing enterprise product in history.
And they make it dead simple to leave.
So why do the rest of you make it so impossibly hard?
The Enterprise SaaS Cancellation Industrial Complex
A 2024 FTC study of 642 SaaS companies found that 76% deploy at least one dark pattern in their digital interfaces. 81% make auto-renewal the default without letting you turn it off during purchase. 67% don’t even tell you when you need to cancel to avoid the next charge. 70% don’t provide clear information on how to cancel at all.
This isn’t a bug. It’s a strategy.
Even Salesforce’s Master Subscription Agreement literally says: “payment obligations are non-cancelable and fees paid are non-refundable, and quantities purchased cannot be decreased during the relevant subscription term.”
You want to cancel Salesforce? Here’s what that actually looks like. You need to be the designated account administrator. You need to find your contract expiration date buried in Setup. You need to provide written notice at least 30 days before expiration — to your Account Executive, who has every incentive to slow-walk you. There’s no cancel button. There’s no self-serve path. And if you miss that window? Auto-renewal kicks in and you’re locked in for another year.
Or take HubSpot — the company that built its brand on being the friendly, founder-first alternative to Salesforce. Their own documentation says it plainly: “Mid-contract cancellations are not permitted.” Want to downgrade from Enterprise to Professional? You can’t do it yourself. You have to contact a “Contract Manager” at least five business days before renewal. Want to cancel entirely? You can turn off auto-renewal, but you’re still paying through the end of your commitment term no matter what.
Personally at SaaStr I spent over a year trying to cancel one WP Engine account. A year. I finally got it cancelled the other day. You have to talk to a human, you can’t email anything, etc. etc.
This is the industry norm, not the exception.
The “Roach Motel” Problem
In UX, there’s a dark pattern literally called the “Roach Motel” — easy to get in, nearly impossible to get out. Sign up in 2 minutes with a credit card. Cancel? Send an email. Schedule a call. Talk to retention. Explain yourself. Wait for processing. Call back when it doesn’t process. Get transferred. Get offered a discount. Decline. Get transferred again.
The average subscriber encounters 6.2 dark patterns when trying to cancel a service. It takes an average of 6.7 clicks just to get from the homepage to cancellation. Amazon Prime had 11 dark patterns in its cancellation flow — so egregious the FTC sued them for it.
The FTC tried to fix this. In October 2024, they finalized a “Click-to-Cancel” rule that would have required companies to make cancellation as easy as signup. It was supposed to take effect in mid-2025. But in July 2025, the Eighth Circuit vacated the rule on procedural grounds. The principle — that canceling should be as easy as signing up — is still being enforced piecemeal through state laws and existing FTC authority. But there’s no comprehensive federal rule on the books.
So here we are. An industry that has collectively decided that trapping customers is a viable retention strategy.
Why Claude’s Approach is the Right One — And Why It Should Be Yours
Anthropic didn’t make cancellation easy because they’re naive. They made it easy because they’re confident.
When you have a product that 300,000+ businesses rely on, where over 60% of business customers use more than one Claude product, where large accounts have grown 7x in a year — you don’t need to trap people. You need to earn them every month.
This is the lesson most B2B founders and operators still haven’t internalized:
If the only thing keeping your customers is the difficulty of leaving, you’ve already lost them.
The data actually supports this. A survey found that 92% of consumers said they’d be more likely to switch to a competitor if a company made cancellation intentionally difficult. You’re not retaining customers with friction. You’re building resentment. And the moment a better alternative shows up — and it always does — they leave with a vengeance and tell everyone about it.
I’ve invested in 20+ B2B + AI companies and advised hundreds more. Here’s what I’ve learned across 13 years of watching SaaS companies scale:
The companies that make it easy to leave are the ones customers never want to leave.
It’s counterintuitive, but it works. When a customer knows they can walk away any time, they evaluate your product on its merits every single month. That keeps you honest. It keeps your product team shipping. It keeps your CS team actually solving problems instead of running a hostage negotiation hotline.
Don’t Let Your CRO Turn Cancellation Friction Into a Revenue Strategy
Here’s the deeper issue, and I wrote about this recently in CROs at Slow-Growth Companies Often Aren’t Really CROs — They’re Chief Price Raising Officers.
When growth slows — from 50% to 20%, or 20% to 10% — the CRO’s job quietly shifts from acquiring new customers to extracting more from existing ones. Price increases, forced multi-year commits, mandatory “AI bundles” nobody asked for, credit multiplier games, and yes — making it as hard as possible to cancel or downgrade.
The data is brutal: SaaS pricing was up 11.4% year-over-year in 2025, nearly 5x the average inflation rate. For Salesforce specifically, price increases now account for up to 72% of forward ARR growth. Not new customers. Not expansion. Price increases.
This is what happens when short-term incentives take over. Your new CRO has to put points on the board this quarter. The path of least resistance isn’t closing net-new logos — it’s squeezing existing customers who have switching costs and can’t easily leave.
We lived this ourselves at SaaStr. A vendor where we’d been a case study for five years, where we’d referred them dozens of customers, where we helped spec and ship one of their top features. New CRO joins the renewal call. “We’re doubling prices.” We asked if he knew we were a reference account. “No, I’m still getting to know the business.” We asked if he thought this was fair. “It doesn’t matter.”
What happened next? We haven’t renewed. We called their competitor that day — one we hadn’t talked to in years. And we’re gone as a reference forever. Is that worth making the quarter?
This is the same mindset that produces cancellation dark patterns. The CRO’s comp plan rewards retained revenue this quarter. It doesn’t penalize the NPS crater, the lost referrals, the customers who are staying but seething, who will bolt the moment a credible alternative arrives.
Here’s the test I keep coming back to: if every customer could leave tomorrow with zero switching costs, would they? If the honest answer is “a lot of them would,” you don’t have a retention strategy. You have a hostage situation. And no amount of cancellation friction will fix a value problem.
The Chief Price Raising Officer might make the quarter. But they won’t build the company.
What You Should Actually Do
If you’re running a B2B company and your cancellation flow involves any of the following, fix it this quarter:
- Requiring a phone call to cancel. Remove it. If they signed up online, they cancel online.
- Requiring email to an account rep. Your AE’s job is to grow accounts, not play goalie on churn.
- Hiding the cancel button. If a user has to Google “how to cancel [your product]” and there’s a whole article about it, you’ve failed.
- Auto-renewing annual contracts without clear, advance notice. Send a renewal reminder 60 days out, 30 days out, and 7 days out. Let them decide.
- Multi-step guilt gauntlets. One confirmation screen is fine. Asking “are you sure?” five different ways with sad illustrations is not retention strategy. It’s desperation.
Yes, it’s fine to ask why someone is leaving. Yes, it’s fine to offer a brief, honest retention offer — a downgrade, a discount, a pause. But do it in one step, not twelve. And if they still want to cancel, let them cancel. Right then.
The Real Retention Strategy
Anthropic’s actual retention strategy isn’t the cancel button. It’s the product.
Claude Opus 4.5 is the most advanced AI model available. Claude Code is generating $2 billion in revenue because developers reach for it when facing their hardest problems. The platform keeps getting better — computer use, healthcare integrations, MCP protocol for enterprise systems, context windows that handle 200,000 tokens.
They’re spending their energy making the product so good that canceling would feel like giving up a superpower. Not making the cancel button hard to find.
That’s the competitive moat. Not a contract clause.
I spend $100/month on Claude. I could cancel with one click right now. I never will. Not because I can’t, but because it’s the most valuable $100 I spend each month.
That’s the retention rate you should be building toward.
Make it easy to cancel. Make it impossible to want to.
