Q: If you had the opportunity to redo your membership site, what would you do differently?

From time to time, folks reach out to me with questions about building a successful membership site. While I certainly don’t consider myself an expert, I’m more than happy to share some of the lessons I’ve learned the hard way while building WP101.com, my community for WordPress beginners. Here’s an example of one of those questions…

Q: If you had the opportunity to redo your membership site, what would you do differently?

For the most part, WP101 has been a “work in progress,” continually evolving since its launch in 2008. As a result, there are many things that I’ve learned the hard way… things I would have done differently if I were to launch the same site today.
1. Choose a robust membership plugin that will grow with your site.
I made the mistake of using a popular membership plugin that made use of obfuscated code, making it impossible to customize as my site matured. The same plugin also did not include support for one of the most popular payment gateways (Stripe), which created additional problems down the road (see below).
Eventually, I abandoned this plugin for a proprietary system that I customized heavily for WP101 — another route I strongly recommend you avoid.
If I were to build a new site like WP101 today, I would choose the excellent LifterLMS. It’s by far the best WordPress plugin for building an online learning site. You can sell courses, create quizzes, track student progress, and much more.
But what I love most about LifterLMS is the ability to create “engagements” — touch points with your students as they progress through a course. You send a personalized email when a student completes a particular lesson, for example. Or award them a badge or certificate of achievement when they complete an entire course. These engagements help restore the human element to online learning, something that is conspicuously absent from most online learning sites today.
Update: We recently migrated WP101.com to LifterLMS! You can read the blog announcement including all the details on how our move went!
But don’t stop with this single recommendation. There are dozens of membership plugins available to you today. My friend and mentor, Chris Lema, has created a beautiful infographic that will help you choose the best membership plugin for your needs, and has written a number of articles comparing WordPress membership plugins.
2. Choose a payment gateway that won’t lock you into your current membership plugin.
While PayPal is certainly the most popular payment gateway worldwide, carefully consider other options before committing to them. In addition to countless nightmarish stories of frozen accounts and suddenly disappearing funds, their support is among the worst in the business, driving many to the brink of insanity.
NOTE: My personal story, along with some technical jargon follows.
TL;DR: Avoid PayPal. Choose a membership plugin that supports Stripe, one of the most reputable and flexible payment gateways out there today.
Initially, I chose PayPal’s Website Payments Pro plan, which integrated nicely with my original membership plugin. What I didn’t realize at the time was that this choice would come back to haunt me down the road.
You see, whenever a recurring subscription is created in PayPal, there’s an important piece of data, called an IPN (Instant Payment Notification) URL, that is saved along with the subscriber’s payment details. Every time a subscription payment is processed, PayPal ‘pings’ the IPN associated with that subscription to let your membership plugin know that the payment was successful, and the subscriber’s account is still active.
The final step in this ‘handshake’ is that your membership plugin must confirm receipt of the IPN details. If PayPal does not receive this automatic confirmation of a successful Instant Payment Notification, they conclude that your account must be fraudulent… and subsequently revoke your ability to process future web payments. Yikes.
Each and every membership plugin creates their own IPN URL, which means if you should ever choose to migrate your site to a new membership plugin, all your existing subscriptions will contain an invalid IPN URL, which means future recurring payments will fail, putting you at risk of having your PayPal account shut down.
You cannot change IPN addresses for existing recurring subscriptions, which means you’ll have to cancel every one of your existing subscriptions, then politely ask all your subscribers to sign up again… a step that will absolutely cost you a number of subscribers, resulting in a loss of recurring revenue.
When I migrated away from our original membership plugin, I chose a 3rd party payment gateway (Spreedly) that specialized in recurring subscription payments. This service handled all the payment details on their own site, eliminating the need for secure sign up forms and SSL certificates on my own site, which I thought was a bonus.
Fast forward to today. We’re stuck again.
Spreedly has been sold to Pin Payments, giving me reason to believe the future of the entire gateway is uncertain. But now that all our members’ payment data is stored on their servers, I have no options for migrating to another membership platform. This particular gateway is far too small to be supported by any of the major membership plugins, so I’m stuck either continuing to use my hacked-together, proprietary membership solution together with this current payment gateway, or migrating to a new membership plugin, which could result in losing most — if not all — of our existing recurring revenue.
Moral of the story? Choose a reputable and flexible payment gateway that will enable you to change membership plugins down the road, should you so choose. If I were building WP101 today, I would use Stripe as my payment gateway, because of their stellar reputation, which is second to none, along with their powerful API and developer tools.
3. Start building your email list from day one!
Because our original membership plugin included the ability to email members directly from within the plugin’s own options panel, I didn’t feel we needed a 3rd party email newsletter service. I was wrong.
Now that we’ve changed membership plugins, I no longer have the ability to email our 15,000 members. My only option is to manually import 15,000 email addresses into a service like MailChimp, requiring every recipient to double opt-in once again, a hassle that will likely result in a significantly reduced audience.
Numerous studies have demonstrated the benefits of emailing your audience on a regular basis. It’s probably the best way to ensure you stay “top of mind” with your members, make yourself available for two-way conversations, and let them know about new products and services that will benefit them.
But beyond the ability to communicate with your current members, inviting new people to subscribe to your email newsletter list before joining your site is a great way to let them sample some of your content and get a sense of who you are. Folks will be more likely to join your membership site if you’ve already offered something of value up front.
MailChimp is a popular email newsletter service that lets you create multiple lists or categories of subscribers, enabling you to send strategic, focused emails to specific groups within your audience (see ‘segmentation’ below).
Then, use a plugin like OptinMonster to include an unobtrusive subscription form on your site that will enable folks to sign up for your email newsletter.
Finally, consider creating a series of pre-written emails that will be “dripped” automatically at pre-determined intervals, incrementally introducing yourself to new subscribers, while also providing valuable tips and insights up front that will add credibility to you and your offering.
4. Get to know your audience. Focus on segmentation from day one.
I’ve only recently begun to focus on this, but I wish I had understood the importance of this practice from day one, because now I have questions about how to better serve our members, and I realize that I can’t say with confidence who our members are.
How many of them are primarily bloggers? What percentage of loud members are wanting to learn how to build an e-commerce site? How many are professionals using WordPress to build a business site, versus amateurs who just enjoy writing blog posts in their spare time?
As you can see, these questions are critical in determining the type of content we create next, how we continue to serve our members in the best way possible, and even what we choose to charge for a membership to our site.
So, what is segmentation? In short, it’s getting to know your audience so you can speak to each member in the way that best connects with and serves them.
Practically, it means dividing your audience into groups based on geography, behavior, events or occasions, or other similarities that allow you to connect with them in the best way possible.
Look, nobody enjoys being mass-marketed.

“You want to go where everybody knows your name,
and they’re always glad you came.
You wanna be where you can see,
our troubles are all the same.”

You can’t afford to treat every person the same way, or communicate with every individual using the same, one-size-fits-all approach. No, you need to communicate with each person in the way that best connects with them, lets them know you understand their specific frustrations and needs, and that you can help them.
No matter how small your audience may be at first, you need to begin focusing on segmentation. Do you know who your whales, dolphins, and minnows are? Not all customers are created equal, and you need to know who you best serve from day one.
Read more from Chris Lema about segmentation.
5. Avoid the temptation to offer cheap or lifetime memberships.
When I launched WP101, I had no idea it would become as popular as it has. Because I thought too small, I initially offered a lifetime membership for just $19.
It was a “no-brainer” price point, which enabled us to build some early traction, but resulted in a tremendous loss of revenue over the years… revenue that would have enabled us to grow much quicker, and better serve our members today.
I knew nothing about the LTV (lifetime value) of a customer, so I didn’t fully realize that a one-time payment of $19 from a member would not enable me to continue creating new content or providing support for that member years down the road. Rather, those initial members eventually become a “drain” on your resources, and wind up costing you more money to support.
It’s a bit of a Ponzi scheme because you quickly become reliant on the income of new members to cover the cost of creating content and supporting your original customers, who are no longer paying you. And it never ends; you’re only able to stay afloat if you have a constant stream of new members, and you’re only as financially stable as your last month.
Today, we offer recurring subscriptions, which enables us to build on a constantly-growing base of revenue so that we can eventually afford to bring on new staff and other resources that will better serve our members for years to come.
Hey, I’m still learning, but hopefully some of these tips will help you avoid some of the pitfalls that I’ve encountered along the way! If so, these hard-learned lessons will all be worthwhile.
Got questions? Suggestions? Post them in the comments below. I look forward to the continued dialog!