Cancelling SaaS Subscriptions Sucks #

Perhaps this could be a nice task for an AI agent product #

This feels like a nicely shaped AI problem. I have too many SaaS and other subscriptions that I’m not using, but haven’t cancelled. Cancelling these subscriptions is a task that’s not so broad like an all-purpose web agent to be too difficult, and it has specific financial value for the user.

The most annoying ones are the ones that make it difficult or complex to downgrade or cancel #

Most annoying to cancel and downgrade so far: AT&T (not SaaS), Webflow (almost as bad as AT&T), DocuSign, Substack, Blueberry Medical, Calendly, Termly, Otter.

The hardest part is often figuring out which email address I signed up with #

Things that I want to cancel but want to keep putting off because I know they’ll be annoying generally fall into one of a few categories:

• Services where I have an account but can’t find which email address I used, it might’ve been prior contractors of mine using my card… Oops
• Services where I have multiple accounts and don’t know which email address I used for the second account (oh how I wish it was a one click cancel button on my credit card statement - Mercury, that could be a cool feature)
• Services where I have lots of stuff I need to export before cancelling

Normally I have everything in my password manager, but it’s the few that slipped through the cracks and are “sign in with Google” that are particularly hard. I could go and check google security settings and get a list of all accounts that use sign in with google from that account, and I probably should, but I’d need to repeat that across many google accounts for myself and figure it out for any team members too.

I still have a list of cancellations I’m wasting money on but avoiding #

The ones I still need to cancel but haven’t because I’m dreading the pain it’ll involve include: Vidyo, Hunter, Podbean, Zapier, Riverside, Convertkit, Super, Kapwing, Streamlabs, Zoom duplicate accounts, Docsend, Canva, D-ID, Microsoft 365, Libsyn, Descript.

It only became urgent because of a credit card expiration #

I had let all of these subscriptions pile up, telling myself that I’d go and cancel them all at some point.

Then I started telling myself that it’ll only be a year or two until AI can do it so I might as well wait until then.

Then one of my credit cards expired and I started getting dozens of “update your card” emails, so I was forced to update/cancel subscriptions because I didn’t want to risk getting sent to collections by anyone! (AT&T, Adobe, I’m looking at you…)

I wished I had a perfect one day executive assistant, or, an AI agent that could’ve handled this #

I wished that I could’ve just handed this task to a one-day executive assistant that didn’t require any training and that I had complete trust in. Just get it off my plate, but get it done perfectly.

I wanted it done now to hit my credit card expiration deadline. Otherwise, I would’ve kept putting it off, it would’ve been at the top of my backlog but not quite urgent enough to get through my avoidance.

The cancellation process was a huge hassle #

I’d wanted to avoid it because I knew (and I was right) that it’d be annoying to do:

• Frustrating websites to navigate
  • Ended up needing to do quite a few Perplexity searches on ‘how to cancel xyz’
• Payment issues
  • Some still sent emails about failed payments because adding a new card didn’t also update the card set for autopay
• Login issues
  • 2fa codes that were difficult to get
• Annoying cancellation flows
  • Webflow makes it incredibly annoying:
    • First need to archive sites (confusing: archived or deleted?)
    • Then need to downgrade
    • Then downgrade the workspace
• Dealing with other backlog tasks
  • Sites where cancellation would first involve doing a backup
• Sites with strange downgrade flows
  • Otter ai doesn’t let you downgrade
  • Have to cancel, let it expire, wait till the end of the period, then re-subscribe to the lower plan
• Aggressive cancellation prompts
  • “If you cancel you’ll LOSE ALL OF THIS”
• Things that required a lot of one-off cancellation effort
  • Substack requires cancelling all the subscriptions one by one

It ended up taking me probably 4 hours of tedious work.

But now I’m in a decent state. I’m saving a lot of money (I had an embarrasingly high amount of unused subscriptions), I’m getting fewer emails, fewer items when I look at my CC statements to track, less notifications generally. It’s like the feeling of having a clean house.

Many SaaS “subscribers” are probably fake “ghost users” #

As an aside, I’m reminded of Slack’s approach to automatically not charge for unused seats on B2B plans. I wonder if they still do that. It’s a nice practice as a company, because then you don’t get fake revenue, you’re forced to ensure your product is useful.

Unlike Slack, I suspect that many SaaS companies are doing the “gym” approach of signing people up and trying to keep them as members even when they know they’re not coming in at all.

I also then used Claude to identify all of my active subscriptions and rank them by cost #

I also took a few of my CC statements and fed them to Claude and had it tell me all of my subscriptions, rank them by cost per year, and gave it statements from multiple cards and had it identify duplicate accounts. Maybe someday I’ll cancel more of those.

A case study: Calendly #

Today, I ranked the list, and picked one to do. Calendly. Was spending $720/yr. Then went down to $288/yr. Then figured out how to remove myself as a user and it became $144/yr. But it took 20+ minutes to cancel and was very annoying. Needed to figure out if I needed any of the features I lost when downgrading, deleted an old user and needed to figure out what the difference between delete and delete and remove account was (Perplexity helped), needed to switch admin and owner roles, then figure out how to remove the account I was using. And then, I can’t remove more seats without undoing my plan downgrade. It’s clear that I avoid doing this stuff because it’s opaque and hard to tell what’ll happen, and then there’s the fear of messing something up, plus all the effort of doing the cancellation, so I avoid it.

We need a Subscription Reaper AI agent #

Enter the Subscription Reaper.

It tells you all of your subscriptions. It tells you what it’d recommend for each. You approve the changes. Then it goes and makes them, and confirms they were all successful.

It’s kind of like an alternative to just cancelling your card and not bothering to update anything (which can work, though some providers will send you to collections, SaaS mostly won’t).

I’m not sure how you’d do pricing. Could you do it as 20% of the first year money saved? Maybe. Probably not.

A subscription reaper could force SaaS companies to keep their products useful to keep subscribers #

It’d also put nice incentives on SaaS companies. If people aren’t actively using and getting benefit from a product, they shouldn’t be a user. It creates bad incentives. Incentives to make it hard to cancel, and lack of incentives to keep the product useful.

Aside: I’m hosting AI Salon discussions on ‘what to do given agi is coming soon’ ‘fav ai tools’ ‘5 year ai forecasting’ ‘is this time really different’ #

If you’d like to attend one, send me an email [email protected]. Some on Zoom, some in person in San Diego.

Perhaps we’ll discuss whether you should bother cancelling subscrptions yourself now or just wait a few years for AI to be able to do it :)

There could be a cancellation-difficulty “wall of shame” #

Which SaaS subscriptions have you found most annoying to cancel? Send me an email or post a comment on HN. Name and shame, I’ll add them to a list!