ProsperStack

Nearly 6 years ago I burnt the ships and launched ProsperStack. Since then: AI everywhere, interest rates 7-8% higher, and more competition than I've ever seen. If you asked me what matters MORE now than it did in 2020 (not less), it's these two things nobody wants to talk about: 1. Financial discipline AI has completely collapsed build times. What used to take quarters can be cloned before your next board meeting, which means there are going to be a lot of companies competing in every category. The ones that win are going to be the ones that are more economically disciplined. - Best go-to-market strategy - Best pricing strategy  - Tightest CAC (Not the ones shipping the most features) The growth-at-all-costs era is over. Competition is through the roof, acquisition costs are brutal, and you just have to make the unit economics work to build something that lasts. 2. Retention - WAY earlier than you think you need it I see it happen all the time. Founders wait until churn becomes a thorn in their side to take it seriously. Then they wake up one morning and realize all of their newly acquired revenue is being completely washed out by lost revenue from churning customers. Even scarier, they don't even know the main drivers of churn because they never invested in learning them. The companies pulling ahead right now are watching the long-term signals (NRR, expansion, cohort health) long before those numbers become emergencies. They're treating retention as a growth lever 2-3 stages earlier than they were just a couple of years ago. Building the product was the hard part in 2020. In 2026, everyone can build. The companies that'll survive (and win) over the next 2-3 years are ruthlessly focusing on the fundamentals.

Mobile subscription apps are leaving money on the table. For years, subscription apps were boxed into Apple and Google’s native in-app purchases. That meant: 👎 high platform fees 👎 limited control over pricing 👎 zero visibility into why users cancel That changed with the Epic v. Apple and Epic v. Google rulings. Apps can now guide U.S.-based users to manage subscriptions on the web. That single shift moves payment, upgrades, and cancellations out of closed systems and back into your control. And the the upside is material. Moving subscriptions to the web allows teams to: 💰 Save 15–30% of revenue instantly by avoiding app store fees ✍ Understand why users cancel through structured churn data 🤝 Reduce churn at the moment of cancellation with smart offers Web deflection also changes how cancellation works. Instead of losing users inside native app store UIs, teams can route cancellations to the web and finally learn, test, and intervene when it matters most. Web billing creates the opportunity—and ProsperStack is what turns that opportunity into measurable retention, helping teams capture churn insights, personalize save offers, and track revenue recovered from would-be cancellations. We break this down further in our latest blog post. Full guide linked in the comments 👇

👀 Most subscribers who click cancel aren't actually done with your brand. On December 16, our very own, Tony Sternberg, will join Jay Myers of Bold Commerce to talk about why customers cancel and how to consistently save 25-30% (or more) of at-risk subscribers. The agenda: - What a high converting cancellation flow really looks like - The silent killers inside most subscription churn journeys - How to turn cancellation flows into retention, feedback, product discovery, and upsell engines If your brand relies on recurring revenue, you should be in this room. 👉 Sign up for the webinar here: https://lnkd.in/gENPHMVP

I spent seven hours one day cancelling subscriptions. SEVEN HOURS There were a handful. Less than 10. They were all subscriptions I would have cancelled long ago had the process been easier. The difficulty, and my lack of patience for clicking through screens to find buried buttons, kicked the can down the road. Why? "It's only $1.99/month." "I'll do it later." "I didn't plan for it to take this long." ...or... sheer frustration and apathy This is by design. Recurring revenue is the lifeblood of subscription business. If your business uses intentional friction to protect profitability, you've completely missed the point. Relationships are based on a mutual exchange of value. Are there valid reasons for friction? Sure. In some cases. Security, return of equipment, discounts that were based on commitment... I get it. But...if it's easy to access a subscription, it should be easy to cancel. #subscriptionfatigue #clicktocancel #digitaltransparency

🎙️ New episode of Retain or Die What if we told you you need to re-earn your customers every 30 days to keep them hooked? This week, Tony Sternberg, Co-founder and CEO of ProsperStack, joins Peter to talk about how better cancellation flows can actually boost retention — and why the best SaaS teams never take renewals for granted. 🎥 Watch the full episode: https://lnkd.in/gsajTXtE #RetainOrDie #SaaS #CustomerRetention #ProductAnalytics #AccoilAnalytics

When Tony Sternberg and his co-founders launched ProsperStack, their MVP was too basic. It didn’t work as planned, and the few signups they got weren’t the right customers. They had two choices: quit or adapt. They chose to adapt. 👉 Rebuilt the product 👉 Moved away from self-serve 👉 Focused on demos & high-touch onboarding 👉 Learned who their real customers were In just 18 months, they turned those lessons into a growing SaaS business. In this episode, Tony shares the ups and downs of finding product-market fit, learning when to pivot, and why sometimes manual beats automation. 🎙️ Listen here: https://saasclub.io/309

We’re excited to announce that we now integrate with Piano — helping publishers combine Piano’s billing and paywall expertise with ProsperStack's subscriber retention tools. One of the first to put this integration into action? The Minnesota Star Tribune. A huge thanks to Toby Collodora, Director of Subscriber Engagement and Retention at The Minnesota Star Tribune, for showing how bringing our platforms together can deliver more flexibility, smarter retention strategies, and a better experience for every subscriber.

Over the last 5 years alone, I've cancelled 150+ subscriptions - and observed or consulted on 100s more. Here's the difference between a good, great, & exceptional Cancel Flow: As a refresher… Cancel Flows are the process customers go through to cancel or deactivate an account. It’s also the business’s final chance to save the customer, collect feedback and leave a lasting, positive impression. Here’s the difference between good, great, and exceptional: __________ GOOD: A good flow asks customers 1-2 questions about why they’re leaving and aims to get to the root cause of churn so that they can potentially address issues later. They’re collecting data, but not necessarily acting on it in real-time. While basic, “good” is better than nothing - and it leaves a solid lasting impression on customers. __________ GREAT: A great flow incorporates save attempts and offers directly into the experience, making it dependent on each customer’s stated reason for leaving. For example, if a customer mentions “price” as an issue, they'll probably get a coupon offer. Alternatively, if a customer says they “need a break,” maybe they’ll get the option to pause billing on their account temporarily instead of full cancellation. __________ EXCEPTIONAL: An exceptional flow dives into customer segmentation with more variations and tailored offers. A few examples: ✅ They tie customer segment AND cancel reason into offers. In other words, decisions are based on multiple data points (e.g., plan type, MRR value, customer tenure, etc) ✅ They incorporate continuous A/B testing to iterate and optimize what moves the needle the most for retention. ✅ They experiment with different offers, discount variations, and copy to maximize effectiveness. These small changes can really add up.

🤔 Did you know nearly half of subscription churn is caused by payment failures? This can quietly eat away at your revenue... Unless you have an effective dunning strategy. Done right (combining automated payment retries and carefully-crafted customer communication), you can recover 50-80% of failed payments—instantly. To learn more, check out our latest blog post here: https://lnkd.in/gpXgZnEA It covers the "what" and "why" of dunning, the key elements of a dunning strategy, best practices for dunning communications, and how to choose an automated dunning platform. See you there 👊