Jake Friedberg

Keeping Customers Engaged Beyond Initial Sign-Up

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All of us want customers on our platforms. However, a sign-up is very different from an engaged user who keeps returning and finding value over time.

Creating the right user experience, without being too intrusive, spammy, or “in your face”, can significantly improve engagement, increase conversions, and reduce churn. In my experience, a platform’s success is defined far more by its active users than by the total number of people who have ever signed up.

Below are a few approaches I’ve seen work well, along with some that haven’t been as effective.

Whats Worked for Me

  • Upgrade banners within the product

  • Re-engagement emails for inactive users

  • Milestone-based emails

  • Short video demos

  • Keeping active online communities

What Hasn't Worked as Well

  • Affiliate Links

  • Overloading users with notifications

  • Paywalls before getting meaningful usage

  • Too many CTAs


As I'm looking to keep my users engaged, I'm curious for your on thoughts:

  • What has worked best for you in keeping users engaged past sign-up?

  • Do you agree with these approaches, or have you seen different results?

  • What’s something you tried that surprised you, either positively or negatively?

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Hossein Yazdi

It’s difficult to keep customers engaged these days, very difficult. Indirectly, your app or website is competing with giants like Instagram, X, other social platforms, and even gaming platforms, where almost everyone is somehow addicted.

But in general, for SaaS platforms alike, I think the best way to keep users engaged (and make them come back) is to provide a source of value for them: create something that gives them direct or indirect benefit, just like PH, here :)

Jake Friedberg

@hosseinyazdi yep, always driving back to that core principle of "the customer is always right".

Thomas P.

I've been meaning to try nudging the user through notification reminders since I've built browser extensions. They allow more flexibility and also allow to make the app invisible when it's not needed, like Honey for example, but I haven't seen many extensions giving minimal reminders to users when they haven't used it in a while. I also think the trend of using AI to dictate what / when to show something in the UI of your app is totally underrated right now, since it'll allow for more enjoyable ui/uxs!

Jake Friedberg

@thomasp0 interesting point on the last part. What are some examples of using AI to show up in the app when relevant, like a contextual intelligence? Have you seen this in other platforms?

Thomas P.

@jake_friedberg I can't tell you exactly which product uses it since it's usually under the hood if it is implemented at all. But for me (I built a youtube learning assistant browser extension) an example of what that would look like would be: log the usage pattern (like when the user has the extension disabled for some time) and then show a reminder notification when they go on youtube every now and then (not all the time) like "Remember you can get explanations as you watch with Gloss, try it again!". That might be overkill, but other more complex apps use it to dynamically switch dashboard options or just the copy of their CTA to fit the current user's persona

Ksenia Sh

I agree that focusing on purchase with CTAs and paywalls is a big no-go. We usually try to look at our product from the perspective of the users and ask ourselves a question: "if we used the platform, would we be happy if..." and it generally helps to switch the mindset. We also noticed that personalised emails help when just starting and getting first customers.

However, i wanted to as you how and where do you manage to keep your communities active online? i feel this is where we struggle the most.

Jake Friedberg

@ksenia_sh yes, being customer centric is key to success and really understanding them and taking their input in, because you they're not always going to be so gracious to work with you especially as you're getting started.

Tbh, right now I use mostly communities of the tools I've used to build One Pager, but I would like to incorporate something like this on my platform someday. (no-affiliated plug for them, but their platform looks nice to encourage community engagement)

Ksenia Sh

@jake_friedberg Thanks for sharing the platform! It does look very nice

Charlie Hopkins-Brinicombe

Lots of thoughts here. But I think you hit the nail on the head with this "a platform’s success is defined far more by its active users than by the total number of people who have ever signed up." 👍

My experience is on the consumer side (mobile and consumer web platforms) so I can speak to that.

The one thing that will always hold true for getting users to keep using a product, more any feature, widget or trick, is making sure the product is 100% aligned with the users core motivations for using it.

For example a fitness app, the reason people use it isn't to workout everyday of their life, it's to live a healthier life from a holistic sense. The route to get their might be to workout more often, keep track of your food intake so you can watch what you eat etc, but that's not the point, or where motivation comes from.

Once that's clear you can use features like reminders, schedules, streaks, achievements, reactivation emails etc to naturally help users get to where they want to be but those things are never the point. They just help users.

At the end of the day attention is expensive, everyone is busy so the more you can help users keep their motivation the better. But the minute you go too far, do something that feels like an 'engagement hack' rather than actually helping, you erode trust and people vanish.

Long term, as long as you stay true to that motivation users will stay with you.

Jake Friedberg

@charlie_hb I agree and really zeroing in on a pain-point without getting sideways is a lot harder than people make it out to be.

In-fact your post has given me some ideas for my own product. But when you can address a pain-point, its a "if you build it they will come situation".

AJ

I think the biggest unlock is making the value something that is easy to make into a habit.

If I have an app where I need to switch context completely to get value vs one that doesn't require it, I'll pick the smaller cognitive overhead any day.

Jake Friedberg

@build_with_aj I see you've built quite a view apps. Have you found this principle true as a lesson learned along the way. Any tips on narrowing down the simplest product a consumer would use?

AJ

@jake_friedberg 

My biggest lesson is a bit counterintuitive. Everyone says solve your own problem the way you want it solved. That's not applicable for most products. You are most likely not representative of most groups of people.

I can't say for certain but the closes I've com to succeeding has been by asking people what they would want to happen, seeing what outcome they want and working from there.

Example, for a flight booking page, what do they want to happen, maybe it's booking in under a minute with email confirmation. But you only know this by asking the right question to your target audience. Don't ask how they want to solve it, ask what solved looks like

Viktoriia

Great breakdown, especially the point about paywalls before meaningful usage.

I'm building a life planner app and made a deliberate choice to give users full functionality for the first few modules before asking them to upgrade. The idea is: let people actually feel the value first, not just see a locked screen. Early numbers show decent session engagement (22+ sessions per device), so it seems to be working so far.

One thing that surprised me positively just responding to App Store reviews personally. It's such a small thing, but a couple of users actually reached out after seeing the developer reply. Turns out people notice when there's a real human behind the app.

Curious with milestone-based emails, how do you decide what counts as a milestone? Is it feature usage, time-based, or something else?

Jake Friedberg

@virtualviki do you have a website, I tried finding your product but couldn't and the idea sounds interesting.

Couldn't agree more about when a real human is behind something people will be more included to engage (I personally get infuriated at the idea of even waiting my time talking to a bot or an avatar, its like the entire internet will become auto-attendants.

My company One Pager is entirely based on putting the human first for better outreach and engagement of customer relationships, it may be helpful for your project as well.

For milestone emails, I've worked in a few saying things like "congratulations on creating 10 One Pagers, can you make 50", etc.

Viktoriia

@jake_friedberg The app is called SelfOS - it's on both App Store and Google Play. Still very early stage (3 weeks live), so no website yet.

Really like your point about "congratulations on creating 10 One Pagers." That's smart - tying the milestone to actual product usage rather than time.

I'm actually about to implement something similar - an in-app review prompt that triggers only after users complete a certain number of tasks. The idea is the same: catch them at a moment when they've already experienced value.