Jailbreaking the Degree, Keeping the Pipes: David Blake’s AI redesign for higher ed - David Blake, Degreed

“It is no longer moral for high schools to have the objective to prepare kids for college.”

That is David Blake at his most contrarian. Blake is CEO of Degreed and one of the most battle-tested operators in edtech and HR tech. He has spent years building products that change how people actually learn. So when he says AI renders the old playbook obsolete, it’s worth listening.

In this conversation, Blake argues for flipping the pipeline: less “four years first,” more continuous, modular, experience-first learning tied to real work. He still wants to jailbreak the degree; the twist is that he wants to keep the pipes. The existing higher-ed infrastructure, he says, will be essential to deliver the redesign.

We get into AI’s pressure on the early-career ladder, why ownership will matter more than wages in a world where capital outpaces labor, and what AI-native, human-centered learning design looks like when it coaches, measures, and builds skills rather than just pushing content.

If you work in schools, universities, or companies, this will push you to rethink “career readiness” in the AI age.

This transcript is edited for clarity and length.

On high school’s new moral imperative

A: Welcome, David. My first question: What's a belief you hold that most people would disagree with?

D: It used to be really easy to answer because my thesis on the world was so contrarian - now the world has caught up somewhat. But to double click, my answer is this: I think it is no longer moral for high schools to have the objective to prepare kids for college.

A: It's very contrarian. Say more.

D: I think sending a kid to college is now a net negative for that individual, that it is going to do more damage in their life on average. And so you are pushing kids into something that, yes, some of them will end up having a net positive experience, but on average, it is now net negative. I'm happy to back that one up with all the evidence.

Recent college graduates are employed at about the same rate as high school dropouts. Non-college grad peers who hold high school degrees are experiencing better employment, as a group. non-college grad peers. That's one. Two, in America, our graduation rate is roughly 65% after time and a half. That’s too many kids who go to college are never going to graduate.

Of those who graduate, we have a roughly 45% underemployment rate, which means they will never use their degree. So only a quarter of the people that high schools send to university are going to graduate and use their degree. And most of them are going to end up with college debt, even those who complete and use their degree.

It's no longer moral for the objective of high school to be sending kids to college.

A: And so, especially in light of what you think AI will do to work, what is the moral alternative? What should the new objective be that high schools are anchoring on?

D: I think we have a huge shift that we have to make. An education has largely meant knowledge, and a teacher's job has largely been to impart as much knowledge as possible. That's what's gotten commoditized. I think, instead, a teacher's job needs to essentially become curating students’ skills and experiences. Teachers need to think of it more like you're helping a high school kid build a resume, rather than you are prepping them for AP tests, for a college application, or for college readiness.

To make that happen, we're going to have to increase the rate of experiential and skills-based instruction (at the high school level). Ideally, we will want to blend work and learning more cohesively and create a smoother transition between the learning stage of life and the working stage.

It used to be binary: all learning, then all work. Slowly over the last 35 years or so, we've seen executive MBAs and part-time students, and these worlds have started to blend. But it will have to blend even more so, because we're seeing this increased rate of unemployment for young people, a trend that also precedes AI. And the way to combat that is not more intensive education, knowledge, or even upskilling. It's to break it down into smaller components and start getting a more blended on-ramp into work.

That looks like more experiences, more skilling, and more episodic, smaller on-ramps into work. It's just so risky to go binary all or nothing in any career at the moment.

On the enduring value of higher education - and why it’s overdue for a redesign

A: What is something you've changed your mind about in the last year or so?

D: I have a mentor who would say it's easier to change a lightbulb than a socket.

I've been on record as being an advocate for jailbreaking the degree and reforming higher education. One of the things I've changed my mind on in the last year is that I actually think the infrastructure of higher education is important - and we should be doing more to integrate with that infrastructure than to try and rebuild higher education from the ground up.

A: So just to thread your contrarian view with this view, it's not that you don't think high school students shouldn’t go to college or that college isn’t useful or needed. It's that you think in its current form, it's unhelpful for economic mobility and progress. You want to see it redesigned.

D: Right. It’s currently optimized for knowledge; that's a huge problem. And it costs too much. That's a huge problem. That's it. You add those up, that's no longer good.

A: And if you flip each one of those, it's a huge accelerant to economic progress.

D: Yep. An engine of experience and skills. College becomes a modular, agile, lifelong system that is accessible, low-cost, and democratized.

On what parents should know to guide their children’s learning

A: So, this is one question I’m asking all of the guests on this newsletter, because it’s the one I get asked the most in the school pick-up line, and at happy hours and other gatherings. What would you tell parents that their kids should be learning in school to thrive in 10 or 15 years?

D: That’s a great question. I am a parent - I have a 17-year-old, 15-year-old, and 12-year-old - so I have to think about this for my kids as well. And I’m finding that my thesis on education is getting tested by my children. Gallup is doing a survey right now asking Americans if higher education is worth the expense. A majority now say no. But if you ask, do you want your kid to go to university? It's still like ninety-plus percent say “yes.”

So, clearly, our children are still a litmus test of our readiness to revolutionize education. There's a recognition that the system needs to change, but when it comes to your own kids, it doesn't always matter about systemic change. We just want what’s best for our kids as we navigate the current moment. That’s why it’s really hard to find silver bullets or one-liners in response to this question.

But I have shared a deep conviction with my kids, which is that AI is going to mean labor versus capital. Labor has already been losing over the last 30 years, and AI is only going to accelerate that. In their lifetimes, they will not want to be paying their rent with their labor. AI will accelerate the collection of rents to the capital holders, not to labor. So whatever their dream is, whatever field they want to go into, I am telling them that they will have to pursue ownership.

So my daughter wants to become a chef, and my son wants to be a pilot, right? (The youngest says she wants to be a YouTube star.) That means they will need to own a restaurant, own a plane. So whatever their dream or goal is, my advice to them is to chase it, but become an owner. Because you do not want to be paying your rent off your hourly rate in the future.

On AI’s impact on the early career ladder

A: How do you think AI is currently changing the early career ladder? Especially the kinds of entry-level roles that traditionally gave people their first professional experience?

D: I think there are two lenses on this issue. The first is that entry-level talent is the easiest to displace with AI. The second is that entry-level roles are the most helped and enabled by AI. It's hard to pull out the data on AI’s impact on the early career ladder right now because a lot of the big trends we are seeing in the headlines predate ChatGPT. So at this moment, it’s difficult to assign the impact of AI on the early career ladder.

But if you look at your typical college experience, it’s often about four parts classroom education, one part study abroad or internship, one part experience. And I think we've just got to start inverting that ratio. The job of high school and then universities, and even the early career workforce, is like giving people learning experiences that are like internships on steroids. We need to amplify what internships are. We need to start getting more real-world experience earlier and then augment that experiential learning with core content capabilities.

A: You work with some of the country's largest employers, which would likely be the ones offering these experiences or needing to partner on that. Do you see interest and appetite there?

D: No, not yet. Most employers are, I think, still asking: “How can I reduce my current workforce with AI?” and then, secondarily, “How do I augment my workforce and make them more efficient with AI?”

That said, alarm bells are sounding in the media. But that urgency isn’t being felt by employers because it is a long-term trend. Think about consulting or law firms: their talent pipelines have been so well established for so long. And now all of a sudden, they can carve out the early parts of that talent pipeline, and it’s making their bottom line better. It's making the firm better. It's making billing hours better. But they're only going to suffer the consequences of having carved out their early talent pyramid five, seven, maybe 10 years from now, not next quarter. We know it's coming - but no one's motivated to address it because they haven’t lived through the consequences of those choices.

On human-centered, AI-enabled educational design

A: Okay, let’s shift a little bit to your work and how AI has started to accelerate what you're able to accomplish at Degreed and in adjacent spaces. What new solutions are you building currently, and what is the big thing that they're making possible that wasn't possible before?

D: Yes, absolutely. Happy to share.

We are now in the market with our AI offering, called Maestro. It is an AI purpose-built for learning. To quickly frame the impact of Maestro: it’s already clear that we have experienced a democratization of knowledge in the digital age, through things like Wikipedia, YouTube, and the proliferation of online content. But universities didn't go away, and neither did a lot of the corporate learning infrastructure. Why? Because while content is accessible, there is still a lot to learning that isn’t supported or done in the current media ecosystem.

So that's where we have focused. ChatGPT, Gemini, Copilot - these tools are the YouTube and the Wikipedia of the AI-age - they are focused on democratizing on-demand knowledge, intelligence, and, of course, productivity and efficiency. But just because these tools deliver information, it doesn’t mean that you, the user, have learned from them. There is much more to learning than simply encountering content.

Secondarily, there has been a shift in AI applications that run on the browser to those that run on your desktop; tools that run on your desktop are essentially purpose-built for whatever you’re doing. That’s the step we're taking at Degreed.

Like many other solutions, we started building our AI to do specific jobs, that is, to be purpose-built. But you still had to come to Degreed to experience the benefit of that. Once you were there, you were experiencing AI in a way that was purpose-built for certain tasks, for simulations, for coaching, for finding and curating content.

But now Maestro runs on your desktop, which means that you now have an AI tutor or coach that exists to help you get better in your development, in your skills, at everything you're doing. While most of the rest of the AI co-pilot vertical is about helping you be more efficient and productive, Maestro gives you notes and action items to help you grow your skills in your role.

Think about if you came out of every meeting or interaction and you got two or three minutes of coaching based on that interaction from a partner who has been with you through all of your other meetings, who knows what your goals are because it's also hanging out with you while you're doing all the rest of your work. It’s a massive leap. It’s not simply an on-demand coach, but a kind of sidecar with you as you journey through your day.

A: From on-demand to all the time.

D: That’s right, yes.

A: Amazing. Ok, I need to ask - what are some of the design decisions you made with Maestro to make sure it's not just synthesis of information and is actually instructional in nature?

D: Maestro is rooted in andragogy (the study of teaching adults) and learning science. So many AI tools help us do a task better, but that doesn’t mean we become any more skilled or smarter in the doing of those tasks. And we are seeing some of the research showing a laziness effect of AI - that the more you use AI, the lazier it allows you to become in your task. That means you’re getting less smart, rather than smarter.

So some of the challenges in designing Maestro have been to ensure that we are taking people on the learning journey. They need feedback, they need practice, they need application. They need to be going through that journey, through that cycle. That means that there needs to be friction in the platform for people to learn. You need to struggle, you need to overcome, you need feedback, you need the game to compromise, you need repetition. Those kinds of experiences actually take you on a learning journey.

A: Right - because people learn through challenge, repetition, and often failure - if a solution takes away that layer, it won’t encourage cognitive development.

D: Correct, that’s absolutely right.

One Small Signal

A: Let’s look ahead and do some future casting. What's a small signal in the world right now that you think others aren't paying enough attention to, but will end up mattering a lot?

D: The data I shared above on unemployment rates for college graduates is evidence of just how upside down higher education has become - it’s getting some press, but not nearly what it should be, in my opinion. And yet, I bet most parents of 18-year-olds did not factor that into their decision as to whether or not to send a kid to college this year.

And I think AI is going to prove to be massive - I think everyone will be better off because of AI. But I think the rate at which people get better off is going to diverge.

AI will bring us to a future where everyone is experiencing some lift, but I also believe we are currently constructing a world where the haves have exponentially more than the have lesses. The gap is already growing at an exponential rate. That's a problem that eventually catches up to us at a societal level, and will have repercussions that ultimately I think will change world borders, country boundaries.

A: What's the prediction you're making now that you think you'll either be very right about or very wrong about?

D: I'm going to send my children to a university of my making.

A: Tell me more.

D: It's been a goal I've had, actually, for a long time. I'm either going to pull it off, or my kids probably aren't going to college at all. So it's going to either be very right or probably look entirely different from what I would have ever imagined.

A: So, ok then - it’s Dad's university or no university at all.

D: Yes, that’s right. We will see if I can make it happen.

A: That’s a tall order, but I can’t wait to see how you tackle it. Thank you so much for this interview, David; I’m thrilled to share this with our readers.

D: You bet, Allison. Happy to do it.