Q&A: Katy Knight’s Quest to Fund Ed Tech’s ‘Deeply Unsexy Things’

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Over the past year and a half, Katy Knight has been on a quiet quest to uncover good education-related tech tools, often powered by artificial intelligence. With access to a bank account nearing half a billion dollars, she’s got money to spend if she finds something she likes. 

But she’ll readily tell you, “There’s just not a lot of stuff that’s worth funding.”

Knight is president and executive director of the Siegel Family Endowment, created by computer scientist David Siegel, a co-founder of the embattled, $60 billion quantitative trading firm Two Sigma. A former Google and Two Sigma employee herself, Knight sees her role as helping to bring evidence-backed tools to market — tools “that we can learn something from.” 

That has led her to underwrite small, often experimental undertakings such as Project Invent, which works with students and teachers to promote design thinking, focusing on student needs and inputs. For instance, if students want to improve the quality of school lunches, instead of asking nutritionists or school staff to design menus, a school would turn to kids to study the problem and suggest solutions. 

She also supports Building 21, an innovative high school network in Pennsylvania, and the Modern Classrooms Project, a nonprofit that promotes instruction paced by students, relying on mastery rather than seat time.

Knight has espoused an approach that she calls “inquiry-driven philanthropy,” searching for schools and startups doing important work — and treating grantmaking “as almost field experimentation” alongside more traditional research she funds. “Everything has an orientation toward, ‘What can we learn from this, success or failure, to give back to the field?’”

She has also said educators and policymakers are missing something in the conversation about classroom technology, reducing it to an “all or nothing” question. “We either have to say ‘No tech’ or ‘Very low tech — lock away the phones, keep the kids disconnected, ban ChatGPT, etc.,’ or it’s ‘We’re all in. Every kid gets an iPad. They’re going to learn on technology all day.’ ”

Accordingly, she has many thoughts on AI, the current panic about phones in schools, and how she separates good ed tech from bad.

This interview has been edited for length and clarity.

The 74: You’ve said your goal is to fund “deeply unsexy things” in ed tech to invest in. As someone who gets email pitches every morning about deeply sexy things that I’m very skeptical about, that was a breath of fresh air. What are “deeply unsexy things?” Why is that important?

Katy Knight: Philanthropy can be very much like the private markets and everything else, consumed by Shiny Object Syndrome. We are just as fallible and just as susceptible to chasing the Next Big Idea, the next sexy thing. And I think that’s fine in some respects. Philanthropy should be risk capital, which means sometimes there’s going to be a sexy thing that will impact the social sector — and we should fund it.

But more often than not, change is happening on the back end. It’s not always something new, and it’s not always using the latest and greatest technology. Sometimes we’re talking about the reality of the digital divide in a place where people want to be talking about generative AI, and that’s not capturing attention. So it’s even more important that we, as a philanthropy with the bully pulpit, are thinking about what are the layers of the bureaucracy that we can tackle to achieve systems change? Even though they’re unsexy from a news perspective or a razzle-dazzle perspective, I think they are actually impactful and interesting.

Let’s talk about some of the things you’re funding, starting with Quill.org, the non-profit that offers free AI-powered writing, reading comprehension and language skills lessons. What’s your thinking there?

Quill is sexy, in that they’ve got this front-facing technology. Everyone wants to talk about consumer-facing tools. What’s less sexy, I think, is that we’re not talking about how it’s the latest ChatGPT model. This is about years and years of actual teacher feedback. It’s about training something really specific. It’s relatively niche. And those are the kind of AI applications that I think actually have the highest potential: Applying a powerful technology to something niche should have outsized impacts. That kind of thing makes sense to me. I think there’s a lot of opportunities for us to think about, “O.K., if we weren’t just chasing the best, coolest image-generating technology, what might we be doing to actually serve student need and teacher need? It starts from asking questions about what matters, what the actual challenges are, and then you get to something that’s useful — even if it’s not as shiny as some of the other ed tech startup things that are coming across your inbox.

You’re also funding Quill and others to develop a “Responsible AI Playbook.” Say more about that.

Even though the social sector is smaller than the private markets in terms of investment in new ed tech tools, if we have even a small chorus of people thinking about responsible AI and pushing back against this overarching narrative that we just have to let it run amok, that’s net beneficial to the field.

Talk about the small chorus. Who are the other singers? 

The big one is the Learning Engineering Tools Competition. The other network we’ve been involved with is the Global Ed Tech Trialing Network. The Jacobs Foundation (based in Zurich, Switzerland) helped found this group of funders, developers and researchers globally who are now thinking together about responsible development, specifically through the lens of “How do we create real-world environments for developers to test their tools and hear feedback from teachers and young people more directly,” rather than just building things that sound like they’ll capture a lot of market share.

Can you say more about the trialing network?

We are funding some of the U.S. work, particularly through our partners at Innovate Edu and Leanlab. Leanlab has been crucial because what they do really at their core is very much aligned with this vision of having real live environments where there’s some co-creation of these tools. We’re funding that work through them. They’ve had two global meetings that I participated in. 

Leanlab Executive Director Katie Boody Adorno has built a very cool, small, nimble organization that’s focused particularly on the notion of the co-design of ed tech tools. They work with startups that are really genuine about wanting to design for impact, not just for investors. And they create relationships with schools to have teachers be paid for their participation and to have teachers actually be testers and provide feedback directly to the designers at these startups. I think it’s just a very cool model for almost an accelerator for impact, rather than an accelerator for marketing.

Do you have thoughts on phone-free schools?

It’s a simple solution to a complex problem. On the one hand, in a vacuum, I might say “Absolutely, we need to be more distraction-free.” And much like when I was in elementary school and they were taking our Tamagotchis away, we’ve got to put the phones away. On the other hand, I understand the complex issues of school safety, of child care arrangements in a world where parents have to work. Thinking about what students are in school for — and what we want them to be doing, and how we want them to be learning, and whether or not we want them to feel so attached to these devices — is a really important conversation. But we can’t divorce it from reality: We live in a really uncertain and sometimes dangerous world, and I understand the perspective of parents who might want to be able to reach their kids during the day in the event of an emergency and other things. 

When I was at the ASU+GSV Air Show last spring, somebody I was with said, “Take a good look around: Half of these guys will be gone by next year.” On the one hand, that seems like a very cynical thing to say. It also seems entirely right. Is it a good thing that companies come and go, that you’re always dealing with somebody who’s got a different vision? Is that a healthy thing for education?

In any private market solution, some cycling of companies and iteration is not a bad thing. I think there’s a mismatch between how the tech startup venture world works and how education products need to work. In the VC-backed startup world, we’re funding a bunch of things with the intention that one or two of them will have 100x, 1,000x returns, and a lot of them will go bust. Those companies are incentivized and encouraged to capture as much market share as possible to achieve that investment return. Whether they are actually impactful to students or not is almost irrelevant in that initial drive to capture market share.

That’s not to say that there shouldn’t be competition and a diverse set of tools that educators can dig into. But if they’re getting served up a shiny new presentation for a new tool that they’re being told they absolutely need every month, that sort of churn is incredibly disruptive. 

How do you separate good ed tech from bad? 

When I hear a startup say that their total addressable market is all 80 million students in the country, I know it’s unlikely that product is worthwhile because there are so few ed tech products — there are so few products in general — that can actually serve every single student in the country. So unless you’ve got a more limited perspective on what the market is, I don’t think you’ve actually aligned what you’re building with the reality of what is needed.

I was heartened to read in journalist Audrey Watters’ newsletter last month that she’s returning to writing about ed tech. She wrote that she’s ready to “dutifully remind you that the future of human and machine learning as envisioned by Silicon Valley’s libertarian elite is a pretty shitty one.” Thoughts?

I love that! I mean, look: Not to zoom out too much, but I think as a society we’ve grown somewhat accustomed to being test subjects for tech companies across the board because everything is free. And they say, “Oh, if it’s free, then you’re the product.” And we are. “We’re releasing a new version of this tool. Your email client is going to change tomorrow.” Do you have any say in it? Nope. We’re very used to living in a world where we’re told what to do by tech platform companies and they will manage just how they see fit.

That doesn’t work for education. That doesn’t work when you have no grounding in learning science, pedagogy, or even just being in a classroom. And so I think that is not just an education problem. It impacts the education sector specifically, but I do think it’s a broader societal concern. Our interaction with technology is not one where we have enough agency.

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