Author’s Note: This post is the third of a series. Each post will focus on each day of Building Blackboard Together 2026 and include a final evaluation of the conference based on my preview and thoughts in June’s blog post about the conference.
Day two of Building Blackboard Together 2026 was notable for two reasons. First was that day was my birthday, and the second (and more important reason for all attendees) was the morning conversation between Matthew Pittinsky and Lev Gonick. A highly anticipated conversation for each attendee. As Blackboard sits at an intersection, where it goes from here depends on the views and visions of these two men. What I expected going in was a friendly conversation between an incoming CEO and a board member. What I actually got was closer to an hour of Matthew Pittinsky publicly second-guessing thirty years of his own industry, with Lev Gonick pushing him the entire way. It was probably the most substantive hour of the entire conference.
The setup and the disclaimer that shaped everything after it
Lev Gonick, ASU’s CIO, opened the session by framing it as an “unplugged” living room conversation with the roughly 800 people in the room. Then he introduced Matthew Pittinsky and immediately handed him the floor with a provocation the two of them had agreed on beforehand: why has the learning management system changed so little in nearly 30 years?
Before Pittinsky answered anything, he laid out a disclaimer that ran through the entire session. He doesn’t officially start at Blackboard until November. He’s in a “cooling off period” after leaving Instructure’s board. And for that reason, he told the room directly that anything he said should not be read as a coded signal about where Blackboard specifically is headed. That disclaimer matters. It means everything genuinely interesting in this conversation was offered as personal, historical, and industry-level analysis, not as an announcement. Keep that in mind as you read the rest of this, and as you read my analysis in the next post in this series.
The theory of change, and where Pittinsky says it broke
Pittinsky walked through the original thesis behind the LMS category: make it obscenely easy for an individual instructor to bring a course online, and a ripple effect would follow. First, the learner would eventually get a surface of their own, not just a series of individual course shells. Second, the digital learning environment would become something like an operating system for teaching and learning, with a long tail of discipline-specific tools building on top of it the way apps build on a phone’s operating system.
His diagnosis, thirty years later: neither of those things fully happened. The category, in his words, “I don’t think we fully put the L into the LMS.” It’s still, in his framing, closer to a course management system than a true learning management system. He was careful to give credit to the people who have pushed the category forward at Blackboard, D2L, Moodle, and Instructure over three decades, and he was equally candid that this is an uncomfortable thing to say as someone about to lead one of those companies. But he didn’t walk it back.
Why it stalled: procurement, imagination, and Blackboard’s own acquisition history
Gonick pushed Pittinsky on why, and the answer that emerged was a mix of institutional and vendor responsibility. On the institutional side, Pittinsky pointed to a lack of imagination in how universities adopted the category and specifically to procurement processes and RFPs that reward checklist features (an adaptive question type, a slightly better gradebook) rather than genuinely new capabilities like an intelligent academic planner. Nobody’s job, in his words, is to be the advocate asking for the thing that doesn’t exist yet.
On the vendor side, and this is the part I did not expect a Blackboard CEO to say out loud, even a future one still in a cooling-off period, Pittinsky pointed directly at consolidation. Blackboard grew for years by acquiring other learning management systems, and a lot of the resulting energy went into integration, feature parity, and looking inward, rather than differentiated R&D. “Blackboard, by acquiring many other learning management systems… ended up putting a lot of our energy into how do you then integrate and consolidate and create feature parity… instead of being less acquisitive and focusing more on product innovation.” He called that a choice, and he called it Blackboard’s responsibility to own, alongside the broader industry’s. Many attendees could also point to Pittinsky’s former company, Parchment, which was purchased by Instructure. The majority of Instructure’s growth and development since launching Canvas has solely been on acquisitions and purchases of companies. One may wonder if Instructure’s future will map similar failures.
AI as an ordinary technology, and the Mark Hopkins log
Pittinsky was insistent on this point: AI is an ordinary technology that happens to be capable of extraordinary things, powered by a scale of data and a scale of computing power, and nothing more mystical than that. He pushed back hard on anthropomorphizing it. No “AI tutor.” No “AI teacher.” A tutor or teacher is a human being. He argued the goal should be a human-to-human-to-human learning experience, with AI functioning as infrastructure underneath it rather than a participant inside it.
That led into the framing for his forthcoming essay, built around the old James Garfield quote but with a twist by Pittinsky, “The ideal college is Mark Hopkins on one end of a log and a student on the other… everybody talks about the learner and the teacher and their relationship. What about the poor log? No one ever thinks about the log, the infrastructure.” His argument is that AI’s real opportunity in education is being a better log, not a better version of Mark Hopkins.
While I can see and understand Pittinsky’s viewpoint, the problem is that leaders in the tech sector have bet big on AI. Many stake their careers on the tool and believe in its powers in almost cult-like ideology, and investment companies have followed (including the private equity companies such as the ones backing Blackboard). His comments may seem “prophetic” to many, but the problem is they are a small cry in the “wilderness” of the sector. I hope that Pittinsky’s voice will be joined by more, but we will have to see where this journey goes.
Assessment as AI’s painkiller and why credentialism is the actual disease
This is the section of the conversation with the most direct implications for how Blackboard is likely to build products, disclaimers notwithstanding. Pittinsky argued that assessment, not content generation, is AI’s real unlock in education, for two reasons. First, the fear around AI and academic integrity is loud enough that no other conversation about AI in education can really happen until it’s addressed directly. Second, and this is the more interesting point, he framed AI this way: “I happen to believe that AI technologies are the symptom. They’re not the disease. The disease is credentialism,” and education’s long drift toward chasing the credential instead of the learning underneath it. He drew a direct line from the 1990s moral panic about internet paper mills, through Turnitin, through Chegg’s collapse the moment a technology emerged that let students bypass the work entirely, straight through to today’s AI anxiety. Same pattern, different technology. It’s a strong case. One that many in the room with some history in higher education have seen play out in classrooms and conference rooms on campuses around the world.
He also drew on his own history with Parchment to explain the difference between a “vitamin” and a “painkiller” in ed-tech. For those unfamiliar with Parchment, the company it created the ability to allow students, schools, and employers to securely request, send, verify, and receive academic credentials online. Commonly focusing on credentials like transcripts, diplomas, certificates, digital badges, and comprehensive learner records (CLRs). The comprehensive, portable learner record was the vitamin: a genuinely good idea that almost nobody was actually trying to solve for. Digitizing paper transcripts was the painkiller: a boring, practical problem that unlocked everything else once it was solved. His argument is that assessment plays the same painkiller role for AI in education now, letting instructors use AI to handle feedback on writing mechanics so they can focus their own attention on substance and tightening the connection between specific learning objectives and the credentials students walk away with. These comments can show that, while not officially a part of Blackboard, the ideals that Pittinsky shares mimic the same core values discussed in the product keynote attendees saw the day before.
Matthew Pittinsky, Radical Incrementalist
Asked to explain the term he uses to describe himself, Pittinsky credited it to a UVA librarian whose name he couldn’t recall, and described it as holding a genuinely radical end goal (a much tighter coupling between credentials and actual learning) while pursuing it through a long series of incremental, practical steps, using Parchment’s own path from paper to PDF to machine-readable data as the example. It’s a useful frame for how he takes on challenges, and possibly his management and leadership style when he takes the helm: big ambition, deliberately boring execution.
The customer panel: Mark Booker, Jennifer Jackson, and Nikki Whiteside
The conversation then expanded to include Mark Booker (whose framing on personalization and connecting course content to student experience tracked closely with the University of Phoenix’s broader AI work featured earlier in the conference), Jennifer Jackson (whose BU Virtual team was recognized at this year’s Catalyst Awards), and Nikki Whiteside from San Jacinto College based in Pasadena, Texas, just outside Houston. The most interesting exchange here was a genuine disagreement in real time: Booker asked how to keep students engaged in a world where AI offers a shortcut around the work, and while Pittinsky answered with personalization (connecting abstract topics to a student’s own interests), Gonick countered with something more structural: teaching the “art of the question” as its own competency and giving students the chance to become creators themselves, citing ASU’s own work having students build things like a GPT-driven conversation between historical education theorists as a way of learning the material and the technology at the same time. Two credible answers to the same problem, on stage, disagreeing with each other. That’s rare at a vendor conference.
Is the LMS itself the thing that’s about to be disrupted?
Gonick used his moderator’s privilege to press one of the sharper points of the session: is “LMS” even the right category anymore, or is the industry defending a boundary that AI, and specifically the frontier model companies (he named Anthropic, OpenAI, AWS, and Google directly), are about to dissolve by building agentic AI ecosystems that stitch together learning experiences without needing any single platform at the center? Pittinsky’s response was more measured than combative: he agreed the term “LMS” is probably wrong and said as much, but argued every institution will still need some organizing technology platform underneath its digital learning environment, whatever it ends up being called. Whether that’s a genuine rebuttal to Gonick’s disruption argument or a restatement of the same category under a different name is, honestly, a fair question to keep asking.
The audience Q&A: a global reality check
The floor discussion is where this session earned its keep. One attendee invoked Simon Sinek to ask what education’s “why” actually is in an age when young people have real alternatives to a degree. Pittinsky’s answer leaned on John Dewey: education exists to prepare people for life, and credentialism is precisely what has displaced that purpose with a piece of paper.
Then Malcolm Murray from Durham University stood up and reframed the entire conversation. “If you look at the clients from Central America, from South America, from Africa, from Asia, they’re not closing schools. They’re trying to build schools.” This contrasts with the demographic decline within the U.S. which Pittinsky and Gonick had been discussing. He pointed out, directly and fairly, that he’s been a Blackboard client for 25 years, has paid a lot of money over that time, and increasingly feels like he’s buying the same thing every year. His ask wasn’t hostile. It was a plea for the rest of the world, and for procurement conversations that produce real value rather than repeat renewals. Pittinsky’s response was, to his credit, unusually humble for a stage like this, “What I have spoken to is framed by my experience and very much an American, North American higher ed context and not a global context… I appreciate you flagging that.”
The session closed with one more audience comment worth repeating in spirit rather than in exact wording: institutions in the room described themselves as hungry for what comes next and hungry for genuine partnership and co-design with their vendors, not just being treated as the account that renews every year. Gonick’s response to that was the closest thing to a direct challenge. “If any of our vendor community that are in the category of the LMS are just expecting universities to keep writing checks without there being one real transparency and dialog… we’re way overdue for not only some humility here… but also I think this idea that there’s lots of insight to be gained… from practitioners, from administrators, from the global community.”
If the thoughts and ideas discussed during the session are any indication of how Pittinsky would lead a company, clients and the entire sector should buckle in, the coming years will be transformational.
Where this leaves things
This conversation is why every single conference attendee was here. This session did something the rest of the conference didn’t quite manage: it let genuine disagreement and genuine client frustration into the room, on the record, without smoothing it over. That matters. If the thoughts and ideas discussed during the session are any indication of how Pittinsky would lead a company, clients and the entire sector should buckle in; the coming years will be transformational.
Day Two Wrap-up and Customer Appreciation Party
The conference wound down with more presentations and roadmap sessions. Roadmaps for Blackboard LMS and Ally will soon be held online; check out Blackboard’s Webinars to sign up for them to see what was announced. Then a brief note on the customer appreciation party event, which was held on site.
Having the event on-site was a relief, as getting transported to a venue and back to the hotel made me feel “trapped” at the event. Maybe that’s just me, but it was a relief. Also, the live entertainment was a really outstanding experience. A live band that did karaoke for attendees. It was remarkable to see clients and Blackboard employees perform with this live band. Perhaps we need to have a “Blackboard’s Got Talent” type of show next year. But the highlight for me at the party was all the attendees singing Happy Birthday to me. And yes, I’m still 22. 😉
Technically Yours,
The Blackboard Guru
