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Intro to AI Webinar

The decision to rebuild Sidecar’s tech platform wasn’t so much the result of a single frustration or a lightning bolt of clarity. Instead, the realization came on slowly in how we used our website and interacted with our members day-to-day. In almost every touchpoint, we were left wanting in the data we gathered, the experience we offered and the capabilities we had to expand. 

Eventually, we had to ask the question: Is there something better out there? 

Turns out, the answer is yes. But first, we’d need to build the structure for it ourselves.

We want to be able to tap into best-in-class products and platforms as we grow, and we want to consider products beyond the membership and association markets to include the true best-in-class tech broadly adopted around the world and in multiple industries. Today, that might mean using a CRM like Hubspot, a virtual event platform like Airmeet and an e-commerce tool like Shopify. We also know that 3 or 5 years from now, we may look to platforms that don’t even exist today. Running a membership organization in today’s world means we have to build flexibility into the very bones of how we do business, and that means we need control of the central data architecture that makes it possible. 

That does not mean, however, that we’re creating a home-grown membership solution — far from it. While Sidecar is part of a family of companies that includes a number of organizations with deep technical expertise, the reason we’re doing this is actually because of how easy it is for a relatively non-technical organization to build something like this.

It all starts with what we’re calling our “Common Data Platform,” or CDP, which will be the single source of truth for all things Sidecar. From there, we can plug in whatever platforms we want to create the user-end experience — and swap them out over time when we want or need to change things up. 

That means every single piece of content in Sidecar’s universe will be easily accessible, and we’ll be able to use cutting-edge AI to recommend the most appropriate content for each user exactly when they need it. At Sidecar, our content spans from blog articles (like this one!) to courses, videos, white papers, discussions in the Sidecar Community, downloadable resources, past and present events, conferences and more. 

In the past, a disparate set of content types like this would mean the end-user (a.k.a. you, our audience!) would pay the price with a disjointed experience, and we’d lose engagement along the way. Building our own flexible CDP as the foundation of our new platform will allow us to layer on top the best-in-class systems for a simple, unified user experience that brings together all things Sidecar in one website and app.

So, why am I bringing you behind the scenes? Because we’re taking you along for the wild ride of creating it. 

Here’s why: One of the key things I tell the staff here at Sidecar is that we have to practice what we preach. If we’re going to urge membership organizations to experiment and be willing to try things that don’t always work out, then we, too, need to make sure we’re up front and honest about when the things we try don’t always work out. We believe there are so many lessons in those stories, and it’s for the betterment of all of our organizations if we can share them. After all, there’s no good in being the first to open a door if you don’t hold it wide for the folks who come after you.  

Think of it like the real world version of “Instagram vs. reality:” There’s the polished, finished product that we all see, and there are the many earlier iterations that got us there. It is in those outtakes where the lessons are, and there’s no reason we can’t all learn from each other as we all seek to help and engage our members. 

What is Sidecar membership?

Let’s start with the basics: What are the capabilities Sidecar membership needs to have? At Sidecar, we create content to help association professionals grow themselves and their organizations. That means all Sidecar members have access to live and virtual events, step-by-step courses, a virtual community, a library of guides and tip sheets, and an archive of all our video content. Plus, we have an organizational membership through Sidecar Teams, which means — at a minimum — some of our members have to be able to add and remove people from their organizational account.

Plus, it’s a functioning subscription, which means we need a tech stack that enables us to stay in touch with members, charge them for membership, offer group rates through Sidecar Teams, create notifications for expiring subscriptions, and market to new members. 

In short: We need to do all of the things a traditional association would want to do online.

Sidecar Membership: First Generation

The journey to our rebuild decision really started in 2019 when the first generation of Sidecar membership kicked off. Back then, we had just a few courses in our learning management system (LMS) and we cobbled together software to manage subscriptions using off-the-shelf WordPress plugins. Our first members came on board after SURGE Growth, and they were able to get started immediately even while we were still figuring out exactly where we wanted to go. 

  • Subscription software: MemberPress
  • LMS: LearnDash
  • Email marketing: MailChimp
  • Newsletter:
  • Payment processing: WooCommerce
  • Community: Discourse

That tech stack lasted us only about four months, as we quickly grew out of it and wanted to offer even more to our members. We also wanted to elevate our marketing strategy and begin to really grow our audience. At the time, we were also dabbling with gated content — that is, asking readers to subscribe after reading a certain number of articles per month. 

Sidecar Membership: Second Generation

Soon came along the second — and current — generation of Sidecar membership. In today’s version, we have all the capabilities we mentioned above thanks to two platforms that are deeply integrated with each other: Ontraport and AccessAlly. We picked Ontraport, our CRM, because it allowed us to create automated email campaigns triggered by interaction within the membership, as well as additional marketing automation features. And AccessAlly was an easy pick because it integrates with WordPress in such a way that, if it ever disappeared, we’d easily maintain all of our data and content. 

  • Subscription software and LMS: AccessAlly
  • CRM and payment processing: Ontraport
  • Community: Tribe
  • Newsletter:
  • Virtual events: BigMarker
  • Integrations: Zapier

The trouble is, the list of new features we want to add is growing … and growing, and many new platforms we want to the tech stack don’t natively integrate with that core pairing in our membership tech. Additional integrations, made possible through Zapier, are only getting us so far. Plus, our membership roster has grown too (yay!), and as we’ve gotten more people using Sidecar, we see and hear about the features that would make our members’ lives easier. 

We’re growing up, and we’re growing out of our current tech stack. 

Sidecar Membership: Third Generation

There are tons of new features we’re looking to build into the next generation of Sidecar membership. (I’m not kidding: The document that details all of them is currently 14 pages long.) But one of the core features of this new platform edition is that we want to create a robust common data platform, a single source of truth that pulls together everything we want to know about our members, including: 

  • Seamless, friction-free user experience for our audience to access every single piece of content Sidecar has to offer
  • Basic contact information and form fill-outs
  • Interaction details with our website, like page visits, downloads and time spent
  • Past and current subscriptions and purchases
  • Organization details based on what’s publicly available via LinkedIn and 990s
  • Work history (important for a professional development platform!)
  • Social media links, like LinkedIn and Twitter

This CDP will be the “brain” in the system, storing everything we want to know about our audience and fed by all the different platforms we end up using to create our Third Gen tech stack. It’s this core functionality that will allow us to plug and play with all the best-in-class tools at any given time, because we always own the source information. Think of it this way: We own the oil and we control the pipelines, which means we can turn on, shut off and redirect supply to the factories that refine it anytime we want to. 

Now, we don’t mean that it would be easy. For example, we’re moving onto Hubspot for our CRM, and as anyone who’s made that kind of transition before knows, it’s not a switch off, switch on process. It takes work! But we want to be able to unplug one platform in a way that we can’t currently, where our current LMS is also our membership management system. 

If this sounds familiar, that’s because it should. The same conversation is playing out in associations around the world who are wondering if an AMS is the end all, be all solution. For us, the answer is easy: No. An AMS or any other type of “all-in-one system” wouldn’t suit our needs, nor give us the level of long-term control or flexibility we need to create the best experience for our audience. Even a relatively flexible AMS and or similar system still exists as the center of its own universe. 

We just need more.

This approach — using a mosaic of best-in-class platforms to support all of your organization’s operational needs — has historically been difficult if not sometimes impossible. Tools like Zapier help make some integrations possible, but those are limited limitations. Native integrations, which allow you to sync data across two platforms without a middleman and without compromise, are finally becoming easier and maintainable. That’s what’s making it possible for Sidecar to experiment with this kind of structure — and if it’s possible for us, it’s possible for many associations to try it, too.

Here’s a quick idea of some of the new features we’re looking for in the next generation of Sidecar: 

  • A robust data platform that pulls together a 360-degree view of our audience
  • Improved capabilities and data gathering for our Teams users, including the option to “assign” courses to team members and download progress reports
  • Global search functionality such that members can search for a keyword and we provide answers regardless of where they’re found on the site, vs. the currently siloed search functionality we have now
  • Improved accessibility for screen readers and captions on all videos (including global search for the video captions, too)
  • Tracking information for members so they know if they’ve watched a video before or downloaded an eBook
  • Wider community functionality with comment streams on all content
  • Improved virtual event delivery allowing logged-in members to avoid logging into another platform
  • AI powered recommendations engine to allow us to suggest the right content at the right time, to each user

And tons more. (Did I mention the 14-page document with all the features?) 

What’s Next for Sidecar Membership

Here’s the thing: All of this won’t happen overnight. In fact, we’ve been working on this project since the fall of 2021, even while we were organizing the digitalNow conference. But we are ready to talk more about it, and that means sharing with you about the journey we’re on to build a better membership experience. 

Our ultimate goal is to unveil the first look at Sidecar’s Third Gen in the summer of 2022. We’re aiming for something clean, easy to use and, frankly, good looking. We want Sidecar members to know they have an unparalleled online membership experience, and we’re creating it with the intentionality and quality of a consumer-grade product of the type you’d find from Apple or Amazon.

So, what’s next? You tell us. We’d love to hear what you think and what you’d like to see in the next version of Sidecar. Email me at with the features you’d love to see in Sidecar, and get a guaranteed first-look at what we’re building by joining us at Sidecar, either as an individual or bring your entire team along. 

We can’t wait to show you what we’re up to.

Chelsea Brasted
Post by Chelsea Brasted
March 15, 2022
Chelsea is a local reporter in New Orleans for Axios, a new media company.