You’ve got a growing membership, but you’re worried about churn. When those annual renewals come up, it’s nerve wracking. You’re wondering what else you can do to keep members with you year after year. More automations? More stories? More events?
We hosted membership pro Andy van Bergen to talk about to keep your members renewing and how to win back ones who have cancelled. Andy’s the Head of Membership at Escape Collective. He and his team use Outpost to the max, running one of the most robust renewal and win back programs we’ve seen. We’ll discuss how Escape set up their system and what you need to know as a member-backed publisher. Check out the recording or read the highlights below.
Watch the recording
Highlights from the Fireside Chat
Q: How is Escape's membership system structured?
It's essentially one big funnel. Visitors hit a registration wall, and once Escape has their email, they enter a free welcome flow. If they convert, they get a paid welcome flow, weekly newsletters, perk reminders, and, if they cancel, a win-back sequence. Most of it is automated through Outpost (free and paid welcome flows, renewal reminders, cancellation flow), and the whole thing runs on a very small ops team: Andy plus a product manager, a dev, and a hands-on CEO.
Q: What's the key to a good welcome flow?
Help people find the one thing that resonates rather than throwing everything at them at once. Escape spreads its welcome flows over 90 days, introducing offerings gradually. If you do nothing else, send one personal welcome email from a real person that invites replies.
Q: What did Escape prioritize early?
Email automations from day one, and a members-only Discord so members could connect with each other, since a membership is a two-way "club" rather than a transactional subscription. Perks came later: a forum and "pro deals" (discounts at cycling brands) that can pay for the membership in one or two purchases.
Q: How do monthly and annual cancellations differ?
Annual members churn at under 1% per month, while monthly churn is over 10x that. Monthly members tend to join for event moments (like the Tour de France), so on cancellation Escape offers a discount immediately. Annual members are almost never discounted up front; discounts are introduced later based on their cancellation reason. Andy also says not to send renewal reminders to monthly members ("don't wake the sleeping bear").
Q: What happens when someone cancels?
A pop-up appears. Monthly members get an on-the-spot discount offer. Annual members choose one of five reasons (too expensive, not using it enough, taking a break, temporary need, or a free-text field). The reason determines which win-back message they get, so no discounts for people who cite low usage and no non-price pitches for people who cite price. Without custom pop-ups, you can pull cancellation reasons from Stripe.
Q: How do you avoid guilting people with too many post-cancel emails?
Andy's strongest window is before the cancellation takes effect, since many people cancel auto-renewal on day one with no intention of leaving. Escape sends one email immediately and two more before the churn date, and it's much easier to get someone to reverse a cancellation than to win them back afterward. After churn, start softly, then push harder, since there's nothing to lose. Ryan added that Outpost holds retention offers until close to the churn date (e.g. not within the first 45 days), and now lets readers opt out of individual flows without leaving the newsletter.
Q: What win-back messages work best?
- Passive churn (failed payments): Use Stripe's dunning flow. It automatically retries cards, even timing retries around likely paydays. This is the churn that "cuts the hardest."
- Active churn: The most effective email is the very first: "Did you mean for that to happen? You've lost access, please come back." Average win-back time is around 60 days. Escape stops the automated flow at about 3 months, then runs occasional one-off campaigns to past members based on their original reason for leaving.
Q: How much is automated vs. manual?
Nearly all of it. The main manual piece is the free-text cancellation reason, which is time-consuming but highly effective because members give precise reasons you can often solve.
Q: How do you handle the "membership cliff" (lots of annual renewals at once)?
Escape launched with 5,000 annual members, so renewals bunched up. Over the years, they used incentives (early renewals, pushed-out renewals) to stretch the cliff to roughly a 2.5-month window. The broader advice is to never pitch only at the finish line. Remind members of value constantly, and use two Outpost renewal reminders (30 days and 7 days out) for annual members. Ryan added that having both reminders also helps cover varying state legal requirements in the US, and that they should be used to reinforce value, not just serve as a legal notice.
Q: How has Escape's mix of supporters vs. perk-seekers changed?
Founding members are the stickiest, driven by the mission rather than transactional benefits. As Escape matured, it added perks (Discord, forum, pro deals) to give a rational reason to stay. The member purchase program saw a "hockey stick" in usage after Escape made a dedicated effort to promote it.
Q: What about members who don't use perks but support the mission?
Escape has a dedicated stream for them that explains what their money enables (funding women's cycling coverage, industry investigations, ad-free independent journalism with no affiliate links). It focuses on the buckets of impact rather than specific content. Lex shared an example: reminding a would-be canceler that $99/year supports 2,000 small businesses kept them on. A little emotional connection is fine. Andy is also working toward a "membership ladder" (tiers by financial support, plus merch and events).
Q: Do you do list cleaning on free members?
Yes, but not aggressively. They're included in targeted promotions, and people who haven't opened or engaged for a long time get removed, since it affects costs and open-rate stats. Granular targeting converts better than scattergun sends. Outpost has a cleanup tool for people who've unsubscribed but are still site members.
Q: How important is the member newsletter?
Very. Escape's weekly member newsletter has a 65-70% open rate, and ~80% of members subscribe. It has the same structure at the same time every week: an intro from a senior team member (behind-the-scenes insight), an editor-in-chief wrap-up of the week's 40-50 stories, announcements and perk callbacks, and a "fun stuff" section buried at the bottom because it's the most clicked. It's 52 reminders a year of what the membership is.
Q: What's Andy's #1 advice for a membership operator facing churn?
- Don't wait until renewal to make your pitch. Stay in constant contact (email, homepage highlights, newsletters) and watch open rates to gauge frequency.
- Have confidence in your product. Give annual members a heads-up before charging them, and don't sneak renewals through.
(Event summary compiled with the help of an LLM)
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