Blackboard Goes Back to the Future (Sort Of): Matt Pittinsky to Return as CEO

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In the Mid-week Follow Up for premium subscribers in mid October, I noted that the specific terms of the Anthology bankruptcy deal, specifically the multi-tiered board rights and control structures, signaled that the controlling owners Nexus and Oaktree were planning a long-term play. These are not creditors looking to flip a distressed asset for a quick cash recovery in 12-24 months; they are structuring the new Blackboard most likely for a 5-to-7-year holding period.

The biggest open question, however, was leadership. If you are keeping the company for the long haul and refocusing on the core LMS, who do you bring in to steer the ship?

Based on my sources, I believe the decision has been made, and it is quite interesting. The new CEO of the post-bankruptcy Blackboard will be none other than Matt Pittinsky.

The Return of the Co-Founder

Yes, that Matt Pittinsky. The co-founder of Blackboard, who recently left Parchment following its acquisition by Instructure and subsequently stepped down from the Instructure board.

At first glance, this looks like a "Back to the Future" moment, bringing back one of the two original visionaries, to restore the brand. But based on what I’m seeing, this is only partially about nostalgia. This is much more about the future of the LMS market.

As readers of this newsletter know, Matt recently wrote a two-part guest series for On EdTech titled "The LMS at 30". In those posts, he argued that we are standing at the precipice of "LMS 2.0," where AI will finally allow the "Learning Management System" to live up to its name, moving beyond simple course management. His argument wasn't just a history lesson; it was a strategic thesis for where he believes the market is going.

Job #1: Stop the Bleeding

However, despite this "LMS 2.0" view of the future, the new leadership faces a stark reality on the ground. Blackboard’s first and most important job is retention of current clients, to stop the bleeding. While Blackboard and Anthology have managed to slow the decline of the install base in recent years, they have not stopped it. Stabilizing the core business is the absolute prerequisite for any future innovation, and given the competitive headwinds, this will not be an easy first job.

This appointment confirms my analysis of the new owners' intent. You don't hire Matt Pittinsky to strip assets and manage decline. He is a strategic thinker, and while he built up and sold Parchment, he is not a financial manager. You hire him to compete, but he has to secure the foundation first.

A Note on Timing

I need to make one thing clear: On EdTech is not becoming a CEO finishing school.

When I published Matt’s guest posts in August and September, neither he nor I had any knowledge of this upcoming role. There was no grand plan. In fact, at that time, there was no "post-bankruptcy Blackboard" role to fill yet. Matt was writing as an observer with a wealth of historical knowledge, and I published it because it was valuable insight for the community. The fact that his thesis on the "AI Era" of the LMS is now likely to become the roadmap for a major competitor is a fascinating twist, but a coincidental one.

What Comes Next

While the decision has been made, it is not known exactly when the transition will occur. Matt is coming directly from the board of Instructure, one of Blackboard’s two primary rivals, and I am sure Instructure’s legal team will be looking closely at non-competes and NDAs and transition timelines. Expect some delays as the lawyers do what lawyers do.

Throughout 2025, some of the biggest questions for the LMS market have been:

1. Will Anthology collapse?

2. Will someone buy Blackboard?

3. Will it survive the stigma long enough for universities to stay?

We now have answers:

1. Yes, it collapsed but in a structured, court-supervised way.

2. No, Blackboard will not be sold; it will be recapitalized and held.

3. And now, with Pittinsky stepping in, Blackboard has a credible narrative for stability and reinvention.

This doesn’t instantly solve product issues, migration fatigue, Ultra adoption concerns, or the ground lost to Canvas and Brightspace. But the post-bankruptcy Blackboard no longer appears to be merely a distressed asset. It’s a company with a founder-CEO, an owner group playing a longer game, and a debt-free runway to rethink the future of learning systems.

The LMS market just got a lot more interesting.

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