Back in June, I wrote a post called “What Blackboard Needs to Say at Building Blackboard Together 2026”, laying out five things I thought the company owed its client community heading into Dallas.
- Strategic clarity.
- An honest case for why existing clients are the real growth engine.
- The new support model was presented and put in front of the room, not just promised.
- The leadership transition was addressed head-on.
- The internal political posturing that’s been quietly eroding confidence, named and fixed.
Now the conference has happened, the fireside chat has been reviewed, and it’s time to grade the whole thing rather than half of it.
Part One: The Conference – in Brief
For anyone who wasn’t in Dallas, or who just wants the headline version without wading through three days of my notes, here’s what mattered.
DevCon came back, and it delivered. After a seven-year absence, Blackboard revived its technical conference track, and sessions on AI-DLC, the new Blackboard MCP server, and Trustworthy AI gave admins and developers the deep, in-the-weeds content a general session never can. This wasn’t a token gesture either. Rich Desiano and an AWS architecture counterpart walked the room through how AI is actually being used to build Blackboard itself, Scott Hurrey demoed an official MCP server that validated months of work admins have been doing on their own to connect Blackboard data into the broader AI tooling ecosystem, and the closing panel opened the floor to unscripted audience questions instead of a scripted wrap-up. Years of public and private pressure from this community, including from this blog, paid off, and Blackboard deserves real credit for actually following through rather than treating it as a one-year experiment. The one wrinkle worth flagging is that DevCon ran opposite the Strategic Leadership Institute, which meant attendees had to choose between them, and that scheduling conflict is worth fixing before next year.
The leadership situation got named, but it took the whole conference to get an answer with any real weight. Bruce Dahlgren confirmed on day one, in a single line during his opening remarks, that Matthew Pittinsky, one of Blackboard’s original founders, is coming back as CEO, likely by year’s end. He wrapped it in a “Back to the Future” line and called it a story you couldn’t have written better, which is a genuinely compelling way to frame it, but it was still an announcement and not much more. It took day two’s hour-long fireside chat with ASU CIO Lev Gonick for Pittinsky to actually show the client community how he thinks, walking through where he believes the LMS product sector has stalled for thirty years and what he plans to do about it, disclaimers about his post-Instructure cooling-off period notwithstanding. Two very different data points from two different days, and the second one mattered a lot more than the first.
The opening keynote set a tone the rest of the conference had to live up to. Stanford’s David Labaree spent an hour walking through the history of how American higher education grew into a massive, loosely coupled system that survives precisely because it resists rapid change, then turned that lens directly on ed-tech and AI. His warning was blunt: tools that let students bypass the actual cognitive work of writing and reading aren’t solving education’s problems; they’re accelerating the field’s worst habit, chasing the credential instead of doing the learning. He compared it to fast food versus a slowly made meal, and he reminded developers and tech visionaries to at least do no harm to a system they don’t fully understand yet. It was a genuinely uncomfortable talk, forcing attendees out of their comfort zones, and I mean that as a compliment. That push to think “outside the box” ran underneath everything that followed, from the product keynote’s own framing straight through to Pittinsky’s argument two days later that credentialism, not AI, is the real disease.
The product roadmap landed as a coherent story, not a features list. Dom Gore’s “reach, teach, demonstrate” framework tied every announcement, the rebuilt Gradebook with its single-click post-all-grades action, Ally’s new PDF auto-tagging, and AVA’s flashcards and pulse quizzes, back to the same three pillars: Learning, Accessibility, Evidence. The scale numbers backed it up too: over a million users across 76 countries, Ally scanning more than 114 million courses, and AVA logging well over 10 million interactions. Security got real airtime as well, and to Dom’s credit, he didn’t try to make it flashy, just direct about the fact that nothing else on the roadmap matters if the foundation underneath it isn’t trustworthy. It landed with noticeably more weight than it would have a year ago given Instructure’s 2026 breach, and Jennifer Ziegenmier’s support model overhaul followed right behind it in the same spirit.
Two new products signal Blackboard is diversifying past the core LMS, for better or worse. Cursive, an authorship-verification acquisition built around keystroke behavior and revision history rather than after-the-fact AI detection, is designed to work alongside Turnitin, not replace it, and it’s already deployed at more than a hundred institutions outside the Blackboard ecosystem. Scholar, a new AI-native academic planner led by a former Picmonic co-founder, is launching deliberately small this fall with a select cohort of institutions rather than a full rollout. Both are smart, well-reasoned bets on their own terms, and both mark the first real product diversification since the Anthology unwind. But they also raise a fair question clients are entitled to ask out loud: how much of the company’s development capacity, and how much of the “debt-free” balance sheet Blackboard has been touting, is now split away from the core LMS product clients actually pay for every year.
The new support model got specifics instead of a promise. Jennifer Ziegenmier laid out single-ticket ownership from intake to resolution, an AI-assisted intake layer, a new customer-facing support portal, an internal Agent Health Center, expanded language coverage to over 40 languages, and a new customer-effort metric tracked alongside the standard SLA and CSAT numbers. That’s a real mechanism, not a vague reassurance, and it’s the kind of granular detail this community, myself included, has been asking for after a year of noticeable quality complaints. She was also candid that the redesign is still rolling out and asked the room for patience, which is a reasonable thing to ask for as long as the follow-through actually shows up over the coming months.
And the fireside chat was, by a wide margin, the most substantive hour of the conference. Pittinsky’s public self-critique of thirty years in the LMS category, including his own admission that Blackboard’s acquisition-heavy growth strategy pulled focus away from real product innovation, his “radical incrementalist” framing for how he approaches big goals through small, deliberate steps, and his argument that assessment is AI’s real unlock while credentialism is the actual disease, all of it went further than anything from day one. Lev Gonick pushed him the entire way, including on whether “LMS” is even the right category anymore, and the customer panel produced a genuine on-stage disagreement between Mark Booker and Gonick about how to keep students engaged. Then a 25-year client from Durham University stood up and told Pittinsky plainly that renewal isn’t partnership, and Pittinsky answered with real humility instead of a deflection. That kind of unscripted friction doesn’t happen often at a vendor conference.
That’s the version for anyone who wasn’t there. Now, the grade.
Part Two: Grading the Conference
I built the rubric below directly against the five asks from June.
Rubric: Did BbT26 Deliver on What Blackboard Needed to Say?
Scored against the five asks from “What Blackboard Needs to Say at Building Blackboard Together 2026,” published June 16, 2026. Updated with evidence from Building Blackboard Together 2026.
| Criterion | What Was Asked For | Evidence Observed at BbT26 | Score |
|---|---|---|---|
| Strategic Direction & Vision Clarity | A clear answer on what Blackboard stands for in 2026, its product vision, and who it’s building for. | The product keynote framed the entire roadmap around three questions (reach, teach, demonstrate) mapped to three portfolio pillars (Learning, Accessibility, Evidence), tied directly to David Labaree’s opening themes. On day two, incoming CEO Matthew Pittinsky independently landed on the same argument: assessment, not content generation, is AI’s real unlock, and credentialism, not AI, is the actual disease. Two separate voices, two separate days, one consistent answer. | 5/5 |
| Existing Clients as the Growth Pathway | Explicit acknowledgment that peer trust among current clients, not sales outreach, is what will win new institutions. | Kelly Herman’s University of Phoenix testimonial reinforced the partnership narrative but stayed implicit. Day two closed the gap without Blackboard having to say the thesis itself: a 25 year client challenged Pittinsky directly on renewal versus real value, in front of roughly 800 peers, and the exchange stayed on the record rather than getting smoothed over. The Catalyst Awards drew 136 submissions from 19 countries, real evidence that existing clients are engaged enough to compete for recognition, not just renew. | 4/5 |
| New Support Model Shared & Feedback Collected | The new support process needed to be presented to clients directly, with a real mechanism to gather feedback rather than just announce a promise. | Jennifer Ziegenmier laid out specifics: single-owner tickets, AI-assisted intake, a new customer effort metric, and an expanded language footprint. Strong on presentation; the room wasn’t visibly used as the “focus group” the original post called for. | 4/5 |
| Leadership Transition Addressed Directly | A direct, contextualized statement on the Pittinsky CEO timeline, rather than continued ambiguity. | Bruce Dahlgren’s day one confirmation was informal and hedged. Day two gave clients nearly an hour of Pittinsky examining the LMS sector’s failures and his own management philosophy directly, though he opened with a disclaimer that his remarks were personal and industry level, not a coded signal for Blackboard specifically. While given a bit clearer start date for Pittinsky, a hard start date remains unaddressed. | 4/5 |
| Internal Unity & Political Posturing Addressed | A direct acknowledgment that internal factional behavior was undermining client confidence, and a visible commitment to fixing it. | This item will always be difficult to score. Internal politics (with a small p) isn’t something that marketing and leadership want clients to see, especially at a conference. However, in passing conversations with employees, there appears to be internal conflict on managing development resources for features and improvements. Will the retirement of the Original experience help with this? One can’t be sure, but clients should keep a close eye not on what features are being delivered, but how previous features have seen delivery timelines slip. A cloud of uncertainity remains over this topic. | 2/5 |
Scored based on data (recordings, transcripts, conversations, and personal evaluations) collected during and after the Building Blackboard Together 2026 conference.
Where Blackboard delivered.
Strategic direction is the criterion that hit the strongest mark on the board. Dom’s product keynote didn’t just list features; it organized the entire roadmap around a repeatable framework: reach every learner, teach well in a world of AI, demonstrate that it’s worth it, mapped onto Learning, Accessibility, and Evidence categories. That’s a real answer to “what does Blackboard stand for” on its own. What pushes it to a 5 is that the incoming CEO said essentially the same thing from a thoroughly different angle a day later, without appearing to coordinate the talking point. Pittinsky’s argument that “assessment, not content generation” is AI’s real opportunity, and that “AI technologies are the symptom… the disease is credentialism,” is the same worldview Blackboard’s product team already shipped, just arrived at independently. When your product keynote and your incoming CEO’s personal philosophy say the same thing without appearing to have compared notes, that’s not a coincidence of messaging. That’s a company and its next leader actually aligned.
The new support model also earned its mark. Jennifer Ziegenmier didn’t just say support is improving; she named the mechanism: single ownership of tickets from intake to resolution, AI-assisted triage, a new customer effort metric alongside the usual SLA numbers, and a real expansion in language coverage to over 40 languages. That’s more substance than “We hear you and we’re working on it.”
Existing clients as the growth pathway lands at a 4 because of something Blackboard didn’t script. Kelly Herman’s testimonial on day one was warm but stayed close to the surface, focused on the Idea Exchange and Office Hours rather than making the explicit “clients are the sales channel” case. Day two made the case for her. When Malcolm Murray from Durham University stood up in front of roughly 800 people and told Pittinsky directly that he’s been a Blackboard client for 25 years and increasingly feels like he’s “buying the same thing every year,” and Pittinsky responded with genuine humility instead of a deflection, that’s the peer-trust dynamic playing out live. It’s harder to fake than a stage testimonial, and 136 Catalyst Award submissions from 19 countries back up that existing clients are engaged enough to compete for recognition, not just renew on autopilot.
Where it still fell short.
The leadership situation comes in at a 4, and it deserves that credit, but it stops short of a 5 for a specific reason. Bruce confirming Pittinsky’s return during his opening remarks, folded into a “Back to the Future” line, was an announcement and nothing more. Day two was different in kind. Pittinsky spent close to an hour walking the client community through where he thinks the LMS category has failed for thirty years, where he believes Blackboard’s own acquisition strategy contributed to that failure, and how he plans to operate once he’s actually in the role. That’s a genuinely substantive look at the person about to lead the company. What keeps this from being a full mark is the disclaimer he opened with: anything he said should not be read as “a coded signal about where Blackboard specifically is headed,” since he’s still in a cooling-off period after leaving Instructure’s board and doesn’t officially start until November. What was left out was a hard start date for Pittinsky. With keynotes stating his start is still “likely toward the end of the year.” Clients got a real person. They didn’t get a real transition plan.
The internal unity question is the lowest mark on the board. Nobody at Blackboard, on any of the three days, stood up and named internal factions, political posturing, or misaligned priorities directly. That part of the June ask remains unmet. This is always going to be the hardest of the five to score, since internal politics, small p, isn’t something leadership puts on a stage at its own conference. What earns this a 2 instead of holding at a 1 came from side conversations with employees away from the keynotes, where more than one person hinted at real friction over how development resources get split across features and improvements. Whether the retirement of the Original experience eases that friction or just moves it somewhere else isn’t something I can answer yet. The tell for clients to watch isn’t which features get announced next; it’s whether the delivery timelines on the features already announced start slipping. Right now there’s a cloud of uncertainty over this one that I can’t clear up with what I have in hand.
The overall read.
A 3.8 out of 5 is a meaningfully good grade, and leaves room for improvement. Let’s hope the company continues in that direction, and overall, Blackboard did the easier half of what I asked for back in June. Then, once Pittinsky took the stage, he did more of the harder half than day one suggested it would. What’s still outstanding is specific: a firm date and a direct acknowledgment from current leadership, not just hallway comments between sessions, that internal alignment is a problem worth naming out loud. If that shows up before Pittinsky’s official start in November, I’ll say so plainly. If it doesn’t, I’ll say that too.
Technically Yours,
The Blackboard Guru
