Budget crunches, look-alike products, and vendors that rarely talk to each other are making it harder than ever for school leaders to decide what to buy, and harder for EdTech companies to stand out. Add AI to the mix, and the sales conversation gets more complicated: fast product cycles, thin data privacy answers, and a market flooded with tools claiming the same features.

Dr. Kip Glazer has a front row seat to all of it. She is principal of Mountain View High School in Silicon Valley and author of Ready to Lead with AI: A Practical Guide for School Leaders. Between running a comprehensive high school, fielding vendor pitches, and writing her pointed "Dear EdTech Companies" series on LinkedIn, she has developed a clear, specific sense of what earns her trust and what ends a conversation before it starts.

In this conversation, Kip walks through what happens on her side of the sales process: the identity crisis AI is creating for leaders used to being the most knowledgeable person in the room, why boutique vendors survive on service rather than efficiency, and why she would rather refer a company to a better fit than force a mismatch.

What You'll Learn

1. Why "stop building solutions in search of problems" became the rallying cry behind Kip's "Dear EdTech Companies" series, and what she wants vendors to ask before they build
2. The specific deal breakers that end a sales conversation for her, from vague answers on student data privacy to AI labels slapped onto tools without real substance
3. How a single referral, or a single decline, moves through a principal's professional network and reaches far beyond one school

Why It Matters

EdTech companies are operating in one of the toughest sales environments in recent memory: shrinking budgets, longer approval cycles, and a wave of AI tools arriving faster than schools can vet them. Kip's account makes clear that a school leader's decision rarely stops with one person. Her professional network amplifies both her confidence and her hesitation, so a single strong or weak interaction can shape how ten other schools see a company. For marketers and sales teams, the lesson is that trust functions like currency across an entire referral network, and price becomes a secondary question once trust is established. Companies willing to say "we are the wrong fit for you, here is who might serve you better" build the kind of credibility that outlasts any single sale.

Resources Mentioned in this Episode:

• Ready to Lead with AI: A Practical Guide for School Leaders
• Kip's book, written specifically for school leaders navigating AI, safety, and the emotional weight of leading through disruption.
• Dear EdTech Companies (Part 1)
• The post that kicked off Kip's LinkedIn series calling out EdTech companies for building solutions in search of problems.
• Dear EdTech Companies, Part 9: On AI Washing
• Kip's take on what changes the moment a product claims to be AI powered, and the tougher questions buyers start asking.
• What Principals Actually Pay Attention To
• Our earlier episode with Chris Lehmann offers another school leader's perspective on evaluating EdTech and building trust, worth comparing against Kip's take.
• Thinkering Collective
• One of the Substacks Kip reads regularly for long-form thinking on education and technology.
• Mark Racine
• Another Substack in Kip's regular reading rotation.
• Center for Humane Technology
• Rounding out Kip's Substack reading list, focused on the broader impact of technology on human behavior.
• Kip Glazer's website
• Speaking topics, articles, and more from Kip.
• Connect with Kip: LinkedIn

Marketing and Education - Dr Kip Glazer

She is the author of "Ready to Learn with AI," and it's a book for school principals about AI. And guess what? There's no school-- there's not really any books for school principals on AI. It's all for district leaders and teachers, a lot of teacher stuff. Anyways, fast-forward, met her at a conference called ASU+GSV, just had the courage to say, "Hey, do you wanna come on my show?"

So in this episode, she gets blunt about really what's, what earns her trust. , also what gets her attention, , and why will she pay more for a company that actually answers the phone. Getting all old school here. So we talk a lot about what it's truly like from her vantage point as a school leader being constantly pitched for 10 million tech products and 10 million education services, right?

It's full of nooks and crannies, , for the marketer, for the salesperson, for the person just creating this company and trying to find a product market fit, for people that are just interested in ed tech. I loved this blunt, honest take of what's truly working, what does she want to buy, all of the things in ed tech.

, and then stick around at the lightning round. Kip talks about the one word about AI that Kip is absolutely tired of hearing. I love, love, love this show. Please enjoy.

ELANA: Welcome to the show, Kip. I'm so glad to have you on. Like everything in education, it's like how you jump and know people, and we ran into each other kind of randomly at ASU+GSV, and now you're on the show, so welcome. I'm so excited to have this conversation.

KIP: Thank you so much for having me

What was some standout stuff?" But then also, "Hey, what are we a little bit cautious about?" So I'd love to kick that question to you to start off our podcast, and for those of you listening, we're gonna jump into all sorts of marketing things as usual, but we're gonna jump into AI in pretty in, in in-depth way too.

But let's start with the ISTE conversation because selfishly, I just wanna learn from you.

KIP: Thank you so much. ISTE is always exciting 'cause you see people from all over the world coming together to talk about education technology, and a lot of the conversation centered around humanity this time, I felt like. People really wanting to lean into how do we encourage human behavior and human connection.

, a lot of s- school leaders were concerned about how we're going to maintain the infrastructure that they are bringing in. Especially with AI now, the devices might have to get upgraded because it requires, when you have tools that are AI-enabled, it does require more powerful machines, right? And also, I was noticing that the products sound awfully similar from one to the next.

ELANA: Mm-hmm.

KIP: how do we really support that? And I was on a panel for a, a vendor, and I actually said, as a school leader, I'm thinking a lot about the identity crisis, and now the teachers and educators are experiencing, and here's what I mean by that.

Educators feel pressure to be the most knowledgeable person in the room. They, they do have sense of responsibility, right? 'Cause you are a- after all a teacher, right? Well, the structure with AI and technology is not allowing you to be easily the most knowledgeable person, whether you are a CEO or a leader or a school leader like me or a teacher.

Like, when you are supposed to be the most knowledgeable person in the room and you are not able to do that for a variety of reasons, and then when your people who are following you are experiencing it, how are you going to support that and manage that? And I think that's the question that all leaders should be thinking about on top of the tech evolution.

Or, "You do this one portion and they do this other portion, and I need to purchase you both, and hopefully you talk together. But if you don't, and then like what if you, one of you goes out of business, but I've built my curriculum on this?" Like, it is absolutely insane.

KIP: Mm-hmm.

ELANA: Like, like they don't, vendors don't talk to each other.

It's not like they're creating this like cohesive ecosystem unless they're a big brand like Cambium Learning or 3P or something, and they've got like brands underneath them. But it is just cr- I mean, how do we expect educators to navigate this, buyers to navigate this, especially with budget crunches and, you know, we've got all this AI stuff that's confusing everyone of what to p- what to purchase.

And, and we're gonna get into that 'cause there's some really good questions you ask if they're an AI company versus not an AI company, or if they're trying to be an AI company, but they're not, all the things. But yeah, I just, it's a crazy world to navigate and I'm glad you're pointing it out as you're going around the expo hall.

Or when you have this technical upgrade in your district and say, "Hey, we're gonna do this, like, upgrade for our system, and can you send somebody to help us manage this or walk through this?" And whichever company that invests in that and have the technology or technical skills to back it up can survive.

ELANA: Yes, and thank you for pointing that out, 'cause it, it-- down the road it might not be scalable for them, but it is ultimately why people continue to stay with them. It is that like white glove support. It's the-- But it's also that human to human, "Hey, we get you. Let's, let's f- let's figure it out." So I love that you pointed that out.

You have a dedicated customer support person, you have a dedicated tech support who speaks your specific district's language or state requirement. And here is something that we have added because your state..." 'Cause education is very state-driven, and that's something that some companies don't think about, is whatever the state says, boom, you turn around, have to do it.

And if you have one or two of those very thoughtful experiences, educators will stay with you. Because they're like, even if you're a little slower, even if you cost another dollar per student, in the long run, the emotional safety of knowing that you got our back is so huge

ELANA: Yes. Huge head nods over here. And I think that's what people need to know as well. So some, some things I heard is that you will pay more for things like, you know, customer support that you know that you can trust, but also state specific things like how do we make sure that we have our guidelines and customizations that we need without having to figure it out ourselves, right?

Like what are the other things that stand out when somebody is saying, "Hey, we got this great product," but what ultimately gets you to sign that you're like, "Yes, I want that. I need that"?

KIP: This is something that I've learned. Education feels big, but it's very small, right? And educators are storytellers. So you have one bad experience with one school or one educator, they'll tell all their friends, and you won't even know that that's happening. And then when you knock on your door, that's the first thing I do.

And it's, it's, it's that sort of like referral, , ecosystem that is so, so important. So I know that some companies when they're dealing with very small companies or like, a, an educator, they might think, "Ah, that person is not a decision-maker." But be careful who you dismissing because that person might be the connector that could get you to someone else that you really need

ELANA: Yeah, I think that's a really good point. We've had other, you know, school leaders on this podcast, and they also emphasize the need to, like, really check in with their PLN, to check into their professional learning network and say, "Hey, what do you think about this?" but I, I'm always curious as a marketer is like, how do those people originally get on the radar of that product?

What are the things that stand out of like, "Oh, that made me pause," in a good way, hopefully?

KIP: Yeah, any product, and I think I might be a little bit of anomaly, to be honest with you, but any product that has sound learning science principles, right? I know that some companies are now hiring learning scientists, which is, I think, is a great thing. So any company that has like, "This is the type of learning science principles that we're grounding our product in, and here's what that looks like in comparison to some other tools."

So being able to speak about why the foundation is strong and also how the implementation had been worked out can be a huge positive

ELANA: Right. Yeah. That's something that doesn't necessarily get brought up, but it is so important when we think about does it-- is it backed? Not only by success and efficacy, but like is it sound in terms of how it was built upon those principles? That's so important. All right, just a couple more marketing questions and we'll get into the AI world.

And we certainly want to engage our current users of educators but we also wanna attract and, and engage in meaningful conversations with potential buyers too. So that's what we're trying to weigh around, and these questions help guide us. But w- what do you think on the social media side? Obviously you're on LinkedIn

KIP: Yeah, and I think LinkedIn is where professionals go to connect with one another. And I would caution any edtech companies just randomly messaging me on LinkedIn and say, "I have this great product. Please take a look." Or, "Can I have 15-minute conversation with you?" Stop doing that. That is like-- And I'm actually pretty polite.

What do you think of it?" And if I have not heard of that vendor, that's also not so great. But also, there are vendors that I've heard of, and I'm like, "Well, their product might be good, but their customer service is terrible," is not a thing that you want anybody to say. It needs to be, "Their product is great, and they take care of people."

ELANA: Yes. Yes. Follow-up question: When was the last time that you signed up for a demo, and like, what made you do that? Like, y- if you're-- It might be you talked to your PLN or, or whatnot, but what actually made you research a company and say, "Yes, I wanna learn more"?

But anyway, like, and then I asked bunch of other people, and they all said they used it. And they, they unanimously said, "It's not the best tool, but it's the only tool out there that will do X," which is a whole another conversation that I wanna have with ed tech companies. So I was like, "Fine. It's not perfect, but we'll just go with that." I didn't participate in demo. I sent my people, right? Like my APs or the tech leaders who will be in the classroom to manage that. The-- and so that was one way to manage. But the, your question was when was I in the product demo. Recently I was in one because my assistant principal had literally harassed me for two years wanting this product, right?

I asked bunch of questions, and I was like, "Okay, thank you so much for sharing. I'll get back to you." And I could tell the person was so nervous, right? And I felt bad. I was like, but that's me. Like, I have poker face, and many school leaders will do that. Either they'll say, "Oh, great. It's so amazing," cricket, or they won't give you, like, indication, because even if I love it, like the product, now I have to talk to my IT person.

So it takes a while to get the product into the school ecosystem take roots, which is one of the things that I wrote about in my Dear EdTech Company series, right? Because if you want fast turnaround, 30 days, 60 days, 90 days, you're setting yourself up for failure. Like, you have to understand the school's ecosystem cycle, and then be patient enough [00:22:00] to work with us so that when we do buy it, you have all these things lined up.

And then you can stay there and continue to make money, 'cause it's usually schools will stay with you once they sign on. Does that

ELANA: Yes, all of those are good. And you mentioned your Dear EdTech Company series on LinkedIn. For those of you that were like, "Oh, I've got to figure that out, where that is," I'll put it in the show notes for you all. It is wonderful. And, I think maybe just if we wanted to pause on that, is there anything you haven't mentioned?

We've been talking directly to the ed tech companies now about what works, what, what maybe doesn't work, needs to be improved, what makes you go into demos, all that good stuff. But is there anything you wanna kind of tie a bow on for, like in this series you were saying, "Hey, maybe we shouldn't do this," or, "Maybe we should rethink this.

KIP: Yeah, the series started with my frustration one night, right? I'm looking at all these great edtech products, and to be fair, I am not anti edtech products. Schools require excellent edtech tools to do our job better, period. So I just want the companies in the, , field to do a better job. But so many of you folks look for problems when you already have the solution.

And if we built X tool, in what ways would this not fit into your ecosystem? How will this land with your people? Like, I wish they'd ask better questions, invite more educators before you build your product

ELANA: Yeah, 'cause then you're just somewhat contributing to the noise. And I, I think that that somewhat rounds about to our initial conversation around ISTE is that, gosh, you just wish that they would talk to each other a little more, right? all right. You talked about AI washing really quickly. I will put your-- a link to your LinkedIn post on that because it is excellent.

KIP: Yes.

ELANA: Do you wanna talk a little bit about that?

KIP: Yes, because, well, again, I might be the exception than the norm. But safety, cybersecurity, student privacy, the level of that question gets exponentially more detailed. Because I've asked those questions of some vendors, and they couldn't even answer, and I was like, "Nope, either you turn it off or you're not coming to my school system."

Give me a break, right? Like, so sometimes you just have to be honest and say there is a difference between algorithm and gen AI, and algorithmic programs that are built on that can be extremely powerful and very useful. And knowing that, that this is how we're using data, who's storing data, how do we cancel the contract and not lose student data should be the question that every single school leader should ask, and which was one of the reasons why I [00:27:00] actually wrote the series and wrote the book

ELANA: Yeah. It's great you're riding the wave. Hopefully you're doing it with intention, but there are all sorts of things you need to do to prepare and make sure you're entering in as responsibly as possible. it's a completely different conversation once you position your tool as AI. So I just thank you for saying that because we've seen the wave now.

And like, I even had friends for the last two years go around ISTE and FETC and just ask basic questions about data privacy, and the majority of vendors could not answer at the time. A lot of them have gotten better to this date because we've evolved, but it just, AI moves so fast, people jumped on a train without thinking about the repercussions and

And I've been calling on everyone to be vigilant and be responsible in building these tools. Because when you release-- And that's another thing that a lot of educators feel very frustrated, that when ChatGPT was released, no one asked us. And now all the demands of figuring it out, how to do this right in schools, are now put on educators and school leaders.

Don't you want that to be good product that is not going to exploit your own children and grandchildren? Let's all come together and do the responsible thing

ELANA: Yeah. Yeah. So well said. Well, I'd like to jump into-- We were already talking about AI. I wanna jump into specifically some things around your book. And for those of you watching on video, I've got it up here "Ready to Lead with AI." It's a practical guide for school leaders, and I love that it's written for school leaders.

KIP: Don't know

ELANA: Yeah. I mean, yeah, see, if you don't even know, it might be true.

KIP: Yeah, baby.

ELANA: I mean, you talked about the identity disruption before when it came to educators in general, , but it's like so exacerbated when it comes to AI. There's so much that we all don't know about AI, and it's moving at a pace that we can't keep up, right?

And so we have this idea that AI is so unsettling to educators who are used to being the most knowledgeable person in the room, right? So how, how do we deal with that? If I've got an AI product, how do I recognize that? How do I support that? How do-- You know, I don't know where to start, but I think you have some thoughts.

Most hands go up, right? "And how many of you want to be a school leader because you want, , you want to make sure your students' learning and s- the education is going well?" All hands go up. And I tell them, "Sorry to disappoint you, but 80% of your job as an administrator has to do with safety, and 20% is instruction." And that is a hard reality to contend with because educators wanting to be school leaders, they love teaching, they love learning, they wanna help. And I said, "The best administrators are actually oftentimes best bureaucrats." [00:32:00] And those two sort of like art of teaching and being a rule follower sometimes do not mesh, right?

So when it comes to AI, that's also part of the safety responsibility that a school leader has, right? Information safety, data privacy, those are safety, like emotional safety of understanding that this is disrupting who you are fundamentally as educator. So my book is written so that there are numerous different constituents a school leader at the site level has to manage.

And I have one extra chapter that the responsibility of school leaders to interact with the field of learning science and now like commercial field of The vendors, and what are some recommendations that I can provide and some of the checklists. So I was trying to be very, very proactive and practical as the AI conversation start ramping up.

Because when you have a knowledgeable school leader who is able to speak about why more and faster isn't always better, and sometimes going slow to go fast is the way to do it, and that you have to have foundational knowledge about what is AI, what is GenAI, how do we look at computer science in digital ecosystem writ large as what is necessary, right?

ELANA: And I don't know it all because it is changing so fast. And we n- you-- like, you talk a lot about culture and school culture in particular, and if you've got a culture of trust and support, you can say, "I don't know it all, but I know that we'll figure it out together," right?

KIP: sure

A lot of my team is, they come from Discovery Education, and we talk about moving at the speed of trust. And, you know, not one school is gonna-- It's not about moving faster and telling your board you're d- using all these AI tools, but so what? To what end? And, and at what cost, right?

KIP: Yeah, what problem are we trying to solve? I say that literally once a day. Like, when we are so in this, like, "Oh, we gotta move fast, and we gotta make a decision," and I'm like, "Okay, hold on. What problem are we trying to solve? Is the new tool gonna s- solve that problem? Or maybe we need to give up using any tool.

And That experience of shifts, right? Like in, before March, I had plenty of people to call, right? Every problem, like I had Rolodex full of experienced school leaders who are standing behind me, supporting me, wanting me to be successful as a first-year principal. Pandemic hit, they all disappeared, and they were calling me because I was a tech coach before becoming a principal, and I had a learning technologies doctorate, and I was working on these different, like, technology NSF project AI initiative things.

And I go, "Okay, now we're back to that mindset again," but it's worse because when you came back from the pandemic, a lot of people talk about the learning loss of the students or their emotional scars, but who's talking about grown-ups? Our teachers came back with a lot more anxiety and stress, and they are barely getting back to, "Okay, we could do this," and you throw AI bomb on them literally, right?

And we need to change the narratives about what educators-- from what educators are not doing to what educators are doing well. And then the product that lets us be the best educators, I think, will succeed.

And I, I, I applaud you for talking about the educators' mental health and the educators' supports because it's, it's, it's a whole nother podcast, but I felt like it was almost weaponized of like, all right, self-care, go ahead. But no one was actually really looking out for educators when they now have learning deficits, test scores, and all of a sudden now you, you need to figure out AI, all the things.

And then is there any kind of thing you wanna say verbally to those listening or jogging as they're listening along to this podcast of how they can get in touch with you, Kip?

KIP: Yeah, I have a website and it's simple, kipglazer.com. And I am reachable via LinkedIn, and I love hearing from people about the questions or feedback on what I wrote, and I think we need to ask more questions, better questions. I used to tell my students when I was a teacher that the one's intelligence is not rooted in the answers that you give, but the quality of the questions.

I think you can really see if somebody is thinking deeply about the solutions based on what type of questions did they ask

KIP: Cheating

ELANA: Oh my God, yes. Yes. we haven't talked much about email on this podcast in, in particular this episode, but I know that people are trying to reach you in email all the time, also in LinkedIn DMs. But what is the worst subject line or maybe even ask that you've ever gotten from a vendor?

KIP: Do you have 15 minutes? Stop. Like, that is like, I filter that out. I have it. It doesn't even reach my inbox anymore, so there's that

Or, you know, like if you had to invest in one area, is it making sure that I'm just available for you, or is it onboarding or knowing that I can professionally develop? Like, what-- Is there a cool standout story or something that, that sparks in you?

KIP: Yeah, I think it's actually the referral attitude. Be upfront about that is not the-- that is not in my portfolio. However, I know this h- another high-quality company that I can refer to you, and then I will even sit on a call with you to make sure that this is something that you want. Because what that tells me, whether I take advantage of that or not, that the person is in it for the long haul, right?

Like, so these people who are thinking or speaking that they're in it for the long term, schools want more of that

ELANA: So anything they can do in terms of like, and actions speak way better than words and all the things they can do, but anything they can do to consistently show up and say, "Hey, we're in it for the long haul and we're not in it for just selling the deal," 'cause we can smell that a while-- a

They don't want one platform this year, another one next year. So they want me to do a good job of vetting each platform so that when we get it, there is a follow-through, there is a professional learning, there is professional learning specific to our local school context, and also their subject, right? So they know that when we build these things, it's not gonna go away in a year or two, and you have to start all over

KIP: Actually, I love reading LinkedIn posts, and Substack is a new platform that I started to dip my toes in, if you will. There are some very interesting thinkers in Substack that write in a long form, so I, I like to read and really think about or engage in a conversation there

ELANA: Yeah. And if you have a couple of people that you're following on Substack we can throw them in the show notes as well, 'cause I'm always looking out for the people that are thinking deeply when our industry is moving so fast

It's that how genuine a person is and how supportive they are, and I've always had lots of conversations with my different friends in different walks of life. And I feel like I become a better human by listening to and engaging with wise female friends, colleagues, mentors, you name it. So I usually exchange phone numbers, and I talk to them on my walk and d- really brainstorm about how to be in this world.

And through those conversations, I've gotten, like, opportunities for keynoting or even my book contract. So I think that, that, that sort of depth of relationship building could be the new trend

You don't necessarily need to go to the stars to do that and have all these thousands of impressions. So I love that you are relating to that personally, you even have as you are navigating, what do I want? Like I'm, I'm a school principal first and foremost, but a lot of those meaningful relationships have become turned into really meaningful collaborations and opportunities for you in that depth.

You're not trying to reach hundreds of thousands of people. Maybe you are with your book, by the way.

Like, that sense of accomplishment, and I think that's really... And or they'll say, "Oh, the story that you told, like, I have a story very similar to that." And hearing from a principal that is going through similar challenges or similar, you know, potholes that they're stepping in made me feel like I could do it too, and, and that, that's really what I hope for.

So I, I thank you for helping our educators by telling the companies to make better products

ELANA: Well, and also to approach it in a way that doesn't waste educators' time and be-- we become a partner. And you've used the word partner a lot in this podcast, which I, which I appreciate, too. So thank you, Kip, for joining us. I think to, to put it like overly in a simplistic way, working in a school, leading a school is one of the most challenging jobs on this planet.

And working in education alone is incredibly nuanced and challenging, and I love that you have that practical aspect of like, here's one thing you can do. And that's what I try to do on this podcast as well. So for those of you that are listening, I want you to think about one thing that Kip said, and if that changes your mindset or you do one little thing, really what we're looking for is scaffolding up and building.

Reviews help us share this knowledge, because without that, I feel like it's selfish not to share, especially in our industry of collaboration. So thank you all. We'll see you next time on "All Things Marketing in Education." Take care, everyone. Thanks, Kip.

KIP: Bye