Matthew Pizzi is Director of Product, Academy and Head of Documentation at Contentstack. Matthew previously built a company, Train Simple, that provided video-based training solutions for Adobe products and web technologies. After its successful acquisition by Pluralsight in 2016, Matthew continued in curriculum and product development with the company. In his current role at Contentstack, he unites AI-powered content and custom LMS development to create learning experiences that meet people where they are.
In our conversation, Matthew shares how he helped strategize and build out Contentstack’s Academy, a learning management and training and certification program. He emphasizes the importance of personalization, especially with an audience that has a wide variety of backgrounds and learning preferences. Matthew also discusses scalability and flexibility as core pillars of Contentstack’s initiatives.
Sure. When I first joined Contentstack, there was an existing learning management system (LMS) in place that the company wasn’t pleased with. My first couple of months involved researching LMS solutions to find what could potentially make sense for us to pivot to. Contentstack has a world-class headless CMS, which had around 80 percent of what we needed. Once I realized that the missing 20 percent was just a presentation layer mixed with logic, I became adamant about building versus buying a new platform.
It took a bit of persuasion, but eventually I got buy-in to build Academy with Contentstack’s technology. We knew we needed omnichannel flexibility to distribute content anywhere and everywhere, as well as to support users with varied learning styles. We also knew that this approach would help us future-proof the platform and enable us to continue to work modularly. We were able to develop the platform such that Contentstack could use the Academy as a real-world test bed and a place to showcase the company’s offerings.
Today, we use Academy to educate users about Contentstack’s platform, as well as to deliver the experience. If our customers want to see Contentstack in action, they can see how Academy utilizes all of the capabilities within Contentstack to deliver a flexible learning experience. I hope to one day make Academy open source for our customers. That way, they can create their own academies and leverage them in the same way.
We knew that the one-size-fits-all approach of a traditional LMS wouldn’t work for us. Our audience spans a variety of different roles — we need to provide content for people in both ICP and leadership positions who are exploring digital experience platforms for the first time. They want to determine if it’s the correct solution for their organization. We have developers deep in implementations and trying to get immediate answers to a problem, as well as traditional users and content editors who need up-skilling on how to use the platform.
Our audience also has different learning needs and styles, and we wanted to make sure that the Academy could accommodate all of them. For example, leaders often need to solve a problem quickly — they don’t want the friction of a login system. They want to be able to get to the piece of content that they need to solve their particular problem. We didn’t want to force a login, which most learning management systems require.
On the other hand, we also have users who want to go through a learning journey and track their progress. For this group, we did need a login mechanism. We need to serve both audiences, and Contentstack in and of itself made that possible. By using Contentstack technology, we’re not confined to the rigidity of a traditional LMS experience — we can build flexible learning workflows.
From the very start, we treated user feedback as a core part of our development process. Our audience spans across many roles, from developers to marketers to executives. We knew that working off of assumptions wouldn’t cut it. We gathered feedback continuously from a variety of channels, and started by embedding lightweight feedback mechanisms directly into Academy, such as forms where users could submit feedback about their experience. That steady stream of insights helped us understand what works for users and where they get stuck.
We also ran targeted user interviews, especially with early groups and internal stakeholders, to see how people were navigating the platform. It’s one thing to ask someone what they think, but it’s a completely different thing to observe them in real-time. That helped us identify some friction points that surveys and user feedback didn’t surface.
Further, we employ behavior analytics. We look at drop-off points, different engagement patterns, search queries, etc., to better understand what users are trying to accomplish when they are in Academy. This helped us understand where we should refine the product. On the content side, these insights helped us understand what learners were really looking for, so we could satisfy those needs as well.
One of our biggest challenges when creating this platform was balancing scalability with flexibility. We knew we needed to support different types of learners, which meant we couldn’t design a rigid one-size-fits-all system. And with that, we had to create a platform that could scale as our content, audience, and use cases grew.
On the technical side, that’s why we leaned into the composable architecture of Contentstack. It gave us the flexibility to structure our learning in that modular, reusable way. The importance of that is the ability to deliver it across multiple channels without duplicating effort. That’s a critical component for scale. If we have a piece of content that satisfies some requirement on the Doc site, it can also be reused in the Academy and vice versa. We can author and create content once and distribute it everywhere.
In terms of trade-offs, designing these flexible content models sometimes adds upfront complexity. We had to resist the urge to over-engineer and account for every use case. Contentstack gave us the ultimate flexibility, but with that, we could easily overdo it and bite off more than we could chew. We had to maintain a simplified layout and standardized formats, not because we couldn’t support more variety, but to promote consistency so we could scale faster and without an enormous maintenance burden.
This is the challenge of product management as a whole, and this initiative was no exception. Academy touches so many parts of the organization, from product to marketing to customer success. Our approach was built around transparency, open collaboration, and momentum. From the start, we established a clear vision for what Academy would be, and we communicated that often, especially by promoting it within the organization.
We needed to communicate the narrative around why the Academy mattered. We shared that our vision is that it would be more than just a learning platform — it would be a strategic driver of adoption, retention, and customer satisfaction. Painting that vision helped us get buy-in early on from our stakeholders and keep them invested in the project.
Throughout the entire process, we had regular touchpoints with all of the core contributors. We communicated with our internal communication tools like Slack, which gave stakeholders something tangible to react to. This approach helped us maintain alignment, even when the roadmap had to make a flex here or there.
Yes, and with Academy, there are two aspects — the content creation piece and the platform piece. Sure, AI is a powerful enabler of content creation, but trust is most important. As a content author, it’s natural to be skeptical of AI-generated content — it often feels generic or “off.” We’ve made it a priority to ensure that our AI outputs are grounded in vetted, high-quality source material.
We use AI to accelerate our content creation, such as to suggest drafts or other documents, or tailor content for different roles. It’s a great partner — it’s like having an editorial team at your fingertips. With that said, there should always be a human in the loop to make sure that anything that’s AI-generated is reviewed and vetted for accuracy.
At the moment, Academy is powered by Contentstack’s personalization product. This enables us to target experiences for different user roles. We can surface developer content for our dev audience, for example. We haven’t relied on AI for this just yet, but there’s potential in the future to use it to show content to users based on their behavior. Further, Contentstack recently acquired Lytics, a personalization CDP. With that addition, we have the potential to create a highly personalized, curated learning experience that adapts to individual needs and behaviors.
I would really like to get to the Academy 3.0 vision that I have — a reimagined user experience that really showcases the power of Contentstack, and also incorporates advanced personalization. Of course, the business will ultimately decide if this is the direction we want to head in.
One of the biggest opportunities we have is to leverage Lytics to power more personalized journeys. I think we’re entering a “post-Lytics” era where only referring to Contentstack’s real-time data activation capabilities. Today, we can tailor content by role, but in the future, we will be able to go much deeper. Ideally, we’ll have adaptive learning paths based on behavioral interests. I think this level of personalization will help users find the right content faster, which will hopefully keep them engaged in the platform longer.
I also see AI playing a bigger role in enhancing the learning experience. We have the opportunity to automate transcriptions and translations, which makes courses more accessible to a global audience. That required a massive lift not too long ago, but now it’s something that AI can handle pretty easily. As AI continues to mature, there’s a real potential to assist with content recommendations and even learner support.
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One Reply to "Leader Spotlight: Building a scalable, flexible LMS, with Matthew Pizzi"
nice post