In partnership with: Outpost for more member revenue
It’s not always about MORE paid subscribers. Sometimes, it’s about building on what you already have.
Ever had a paid subscriber cancel AND THEN try to win them back?
*cue up the rom com moment*
Unlike winning back a lost lover, winning back a canceled subscriber is easy! Safe! And rewarding!
This summer, we are winning back your lost subscribers.
We ran a win back sprint through all of July 2025. I’m recapping each session below, along with full instructions on how to set up your own win back campaign. Read on!
In this play
- What is a win back campaign?
- Swipe files and examples
- Your win back campaign recipe
- Tips for your win back campaign
- Segmentation
- CAMPAIGNS vs AUTOMATIONS
What is a win back campaign?
A win back campaign is targeted at lapsed customers to get them back and buying again. It’s commonly used in e-commerce and in software as a way to get previously paying customers to come back.
It can also be used ahead of a list clean as a way to “win back” inactive readers, but for our purpose, we’re using it for winning back paid subscribers or one time donors.
Win back campaign example from The Washington post (7 total emails)
Swipe files and examples
View some examples in this deck OR in our Swipe Files (you may have to “load more groups” on the right side of the screen).
Your win back campaign recipe
I recommend you send three emails either immediately after someone cancels OR on a delay of 3-6 months. Here’s an example recipe you can use to build your campaign.
Email 1: Your subscription made this possible
- Opening: Thanks to your contribution, we were able to [FULFILL OUR MISSION/GROW TO A CERTAIN SIZE/DO SOMETHING SPECIFIC]
- Middle: Here’s a few things your contributions made possible. [HIGHLIGHT NOTABLE STORIES, NEW HIRES, EVENTS, ETC]
- Closing: Invitation to renew
- Big button! Or two!
Email 2: Is it time to rejoin us?
- Opening: is it time to rejoin us?
- Middle: Here’s what we’ve been up to: 2-3 highlights paid subs have received or public features
- Closing: Invitation to renew
- Big button! Or two!
Email 3: What’s coming next
- Opening: We have some exciting plans
- Middle: Here’s what to expect in the next [MONTHS/YEAR]<-Keep it generic if you want this to be evergreen
- Closing: Invitation to renew
- Big button! Or two!
✏️ Use my Google Docs template to draft your campaign before you set it up in your email tool.
Tips for your win back campaign
DO
- Present your work as a value add
- Highlight as many perks as you can
- Recap what their contributions make possible
- Tell them why now is the right time to come back
- Use BIG BUTTONS high up
- Sign this with your name
DON’T
- Rely on fancy formatting
- Make these emails too long
- Include more than 3 links (unless they go to perks or the renewal)
- Guilt trip them
- Use “we miss you” or other lies that will come off insincere
Timing
- Option 1: Send immediately on cancel
- Pros: Can win back people who didn’t mean to cancel, Might learn why people cancel too
- Cons: Isn’t probably enough on its own
- Option 2: Send on a delay (3-6 months later)
- Pros: Gives them space to want to return, Often solves for momentary budget problems/story problems
- Cons: Timing is hard to nail
- Option 3: Send every 6 months-1 year
- Pros: Continues to leave the door open for their return
- Cons: Not as easy to set up in automations
- Win back campaigns are usually at least a few emails (2-3) but you can also send them as one offs
- If you send it as a campaign, send them every couple days
- Optionally tie your campaign to another campaign, like “Pitch in on our annual subscriber drive by renewing your subscription”
Segmentation
You can send this campaign or automation to everyone who canceled.
Reasons to NOT send to everyone who canceled:
- You have a segment of people you purposely canceled
- You have multiple tiers and can’t speak to them the same way (and thus have to create multiple win back campaigns)
- Your tool makes it unreasonably complex to include everyone (as in you have to choose one tier or a date range)
Otherwise, send to all churned subscribers!
Two ways to create your canceled segment:
- Use your email tool to create a segment based on a “downgrade” or “cancel” action (possible in beehiiv and Buttondown)OR
- Download a list from Stripe by going to https://dashboard.stripe.com/subscriptions?status=canceled and exporting “ALL” → then delete any you don’t want to include, re-upload this as a CSV and create a static segment inside your email tool
CAMPAIGNS vs AUTOMATIONS
You can send a win back campaign any time (manually) and you can also automate your win back messages on your reader’s lifecycle (automations).
Manual campaigns:
- Sent on business timeline (When you care about bringing back subs)
- Can be timely/have timely messaging
- Can be scheduled like normal emails
Automations:
- Sent on the reader’s timeline (Based on their actions)
- Needs to be evergreen messaging
- Needs to be automated within your email tool or with an outside tool like Zapier or Outpost
Why might you do both? Because you can tie win back messaging into another drive or goal you have and motivate more subscribers to come back.
Manually sending your campaign
It’s a good idea to send your campaign manually before turning it into an automation for two reasons. One is that you can reach long canceled subscribers that an automation wouldn’t reach and the other is that you can pay more attention to how it performs and make adjustments before you automate.
Take your campaign copy and your segment and schedule your campaign! Send the emails 2-3 days apart and you can exclude your normal newsletter send day, if it’s easy, otherwise, I would not sweat it.
Automating your campaign
- Adjust your messaging to be evergreen (remove seasonal messaging or recent stories)
- Make sure you have a reliable label for “downgraded” or “cancelled” in your tool (or use Zapier to add that label)
- Add your emails and add any delays (0-24 hours for immediate notes) and 3-6 months for delayed emails—whatever you want to try and whatever your tool will allow!
- IMPORTANT: add exclude labels/tags or true/false branches that opt anyone who upgrades again out of the rest of your win back campaign
Tool based tips for automations
- Buttondown: Use “When a subscriber cancels their paid subscription” as the trigger
- beehiiv: Use Downgraded from any paid tier as the trigger
- Ghost: Use Zapier (with Stripe → Canceled subscription as the trigger) and make the action Find a member, then Update Member and add a label that designates them a canceled subscriber
- Zapier: Use Zapier to send emails from your Gmail/personal email for immediate cancel win back notes (Trigger is Stripe → Canceled subscription and Action is Gmail → Send email)
- Andy pointed out you can have Stripe notify subscribers of cancellations too. Check that out at https://dashboard.stripe.com/revenue-recovery/automations?create=automation
Stripe’s cancellation email
📺️ Catch up on the live sprint sessions!
Session 1: Plan your campaign
Session 2: Get your campaign ready to run
Session 3: Automate your win backs!
