Note: I am sharing today’s post in front of the paywall for two reasons: 1) to share a correction to the Matt Pittinsky story more broadly, and 2) to share important information previously shared with premium subscribers regarding the accessibility rules. Interested in hearing this information directly? Upgrade to the On EdTech+ newsletter.
Important Update on Pittinsky Story
Earlier this week I shared the news that Blackboard co-founder Matt Pittinsky was heading back to lead the post-Anthology Blackboard.
After that post I heard from multiple sources as well as a Bloomberg article that the story was not as clear as I thought, and I added the following update to the post.
Update 19 Nov: I’ve heard from several sources that the role is executive chairman, but I’ve also heard that Pittinsky would be leading the company. In other words, technically not CEO. I am working to get clarity on this issue and will send out an update. But in the meantime, I have changed the reference from CEO to executive chairman leading the company. I apologize for the confusion.
Most people read On EdTech as an email newsletter rather than going to the website, and I wanted to share this correction more broadly.
Having said that, I want to emphasize that an executive chairman of a company board is not the same as a chairman. While a chairman leads the board and provides oversight, an executive chairman is a quasi-operational role, a senior executive who also leads the board. It is more powerful, and often transitional.
I think that we’ll find the transitional nature to be of interest in this case. For how long will Pittinsky be an executive chairman, when will a CEO be appointed, and who will take that job.
Anthology’s Bankruptcy Plans Now Set
As a reminder, the Anthology bankruptcy plan was to sell off the Enterprise Operations business line (SIS and related offerings along with the Anthology brand) to Ellucian, to sell off the Lifecycle Engagement business line (CRM, alumni engagement, and related) along with the Student Success business line (help desk, OPM-like services, enrollment support) to Encoura.
The process was based on stalking horse bids by Ellucian ($70 million) and Encoura ($50 million) subject to an auction process. As of the end of last week, those two bids were formally accepted as the successful bids. In other words, no new offers of any credibility. So the sale plans are formalized, and the post-bankruptcy Anthology will essentially become the new Blackboard, focused on the Teaching and Learning business line.
We don’t cover ERP stuff too much at On EdTech, but I will note the biggest three open questions with the breakup / sales.
Will Ellucian retain the Anthology Student (SIS) product line or instead force a migration to Banner or Colleague?
Relatedly, what percentage of Anthology clients will Ellucian be able to retain during this integration process (and which ERP companies will benefit from any attrition)?
What will Nexus-owned Encoura (and other Encoura EdTech portfolio companies) do next with its expanded footprint in the ecosystem?
Instructure’s Improved IgniteAI Messaging
As part of my coverage of InstructureCon this year, I had a significant complaint about Instructure’s messaging around its AI announcements (which dominated the conference news).
Very few features or products promised last summer have made it to production, and Siri is as bad as ever. The overall Apple Intelligence has shown that the company has something deeply wrong in its product approach, at least within the emerging AI world. Apple executives get defensive and claim some wins in the AI space, but its credibility took a major hit due to this lack of delivery - even if Apple is still financially successful.
That is the risk that Instructure faces. It is not necessarily that it faces the loss of its revenue or market lead, but having an AI story on stage with little to actually show for it in production is not going to work much longer. You don’t want to be the Apple Intelligence of EdTech.
During InstructureCon, there were no timelines mentioned for the big announcements. None of the news is referenced in the public roadmap. There were whispers that the touted early adopter testing of the Ignite Agent saw something quite different than what was presented on stage - from just one month ago.
This raises one of the two big questions for the rest of 2025 in the LMS market (the other being Anthology’s debt restructuring). Is Instructure’s bold AI vision real, or is it half-baked and missing timelines because the company itself does not know what is left to finish products?
I should give credit where it’s due - Instructure put out a video this week on its IgniteAI product plans, and it is much, much better. Instructure is now listing specifics on release dates - what is available now, what is due from December through early 2026, what is free vs. what might have an additional cross-sell fee after June 2026.
Now we can see specifics on the reality of product updates.
Kudos to Instructure for the messaging improvements. I’ll evaluate the specifics of the announcements across the LMS market in the coming weeks.
About the DOJ Accessibility “Deadline” (re-sharing after last week’s post)
The post “The Other Regulatory Time Bomb” about the upcoming DOJ accessibility rules, with effective dates of April 2026 and April 2027 (depending on population served) has stirred up a lot of conversation. The basic idea is that public institutions need to comply with WCAG 2.2, Level AA, which means accessibility requirements for all actively-used website information (including on LMS and other password-protected sites) - and the two biggest issues for universities is remediating hundreds of thousands of PDF files and the new audio description requirements. Few colleges and universities are prepared, and few vendors are fully supporting the requirements.
Perhaps the biggest question I hear is whether this is truly a deadline (hence the scare quotes), in other words, whether all content and websites need to be compliant as of April. A lot of people believe that there will be an on-ramp period, where institutions can show progress and have processes in place and this will be enough. Other people believe April is a true deadline and full remediation is due in six months.
The more I look at the details, the more I believe the latter position is (mostly) correct. Full remediation. Why do I say this?
Conceptually, we are already in the transition period and April is the “time’s up” moment. The regulations were published in April 2024, and the two-year period is the on-ramp.
Specifically, a lot of people are relying on an apparent exemption in the rules for “preexisting conventional documents” that includes PDFs. But this exemption only applies for archival, non-used content. This was described in an Ogletree 2024 post. [Emphasis added]
The regulation also defines and exempts preexisting “conventional electronic documents,” which are defined to include PDFs, word processing documents, presentation format documents, and spreadsheet file formats. Again, this applies only to documents in existence at the time of the regulation’s compliance deadline, as long as the documents are not later needed or used to apply for, or gain access to, the entity’s ongoing programs, services, or activities. Any documents still needed in the post-compliance deadline period - that is, for current purposes - must be made accessible, even if they are preexisting conventional documents.
In a related note, a lot of people are assuming that the DOJ will delay the rule, partially based on its Spring 2025 agenda item talking about a delay or change in the rules. But there are three big problems with anyone relying on a delay.
There has been no update since the Spring mention, and the clock is ticking.
Any changes to the regulation would need to follow Administrative Procedure Act (APA) process (notice of changes, public comment period, revisions, etc). It’s not clear that the DOJ would have time to make changes before April.
A counter-argument is that the DOJ could just issue a stay or delay the effective date for the rules. Theoretically this is possible, but to do this by not follow notice-and-comment would require the DOJ to rely on a “good cause” for an immediate stay. And the courts have been quite restrictive in allowing these exceptions.
Even if the DOJ intends to delay the rules, there would likely be a confusing period between April and when the final rule changes could be implemented or a new effective date defined, which is risky.
Everything I’m reading indicates that April 2026 is a real deadline with few exceptions other than archiving of content.
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