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Episode

10

How a Silicon Valley Microschool Actually Buys EdTech

Published:
June 18, 2026
32
min
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A 30-student microschool buys nothing like a district. Joseph Dalton-Stark, founding principal of Leadways in Cupertino, joins Peter Polygalov and John Faig to explain how a brand-new independent school actually buys edtech: why he avoids long lock-ins in year one, skips pilots, wants onboarding speed over a five-year roadmap, and quickly writes off vendors who pitch him a district-sized price or the wrong firmographics.

What you'll learn

  • Why a new school avoids long-term lock-ins in year one
  • How a 30-student microschool's buying differs from a district's
  • Why a district-sized price quote ends the conversation instantly
  • What onboarding speed, not a five-year roadmap, a founding principal wants
  • Why both a microschool and a private school skip pilots
  • The outreach that gets through: warm LinkedIn, referrals, good timing
  • Why edtech marketers should study other industries' content
  • Focusing on your ICP and anti-ICP, not the polite middle

Chapters

  • 0:04 Meet Joseph Dalton-Stark and Leadways
  • 1:37 Building a school's edtech from nothing
  • 2:26 Year-one advice: avoid long lock-ins
  • 3:48 Selling to Silicon Valley families
  • 4:48 What earns a tech director's attention
  • 5:42 A principal's first filter: evidence and real use
  • 6:39 A tech director's infrastructure filter
  • 7:09 Tells that a vendor hasn't done the research
  • 9:07 The channels that get through
  • 11:33 How the channel mix differs for a tech director
  • 13:43 Does vendor content marketing land?
  • 15:37 Peer networks and a shared tech-stack matrix
  • 18:09 Marketing Learner Mindset, and unexplored channels
  • 19:31 What vendors get wrong pitching AI
  • 21:33 One assumption about private K-8 that falls apart
  • 23:04 Pilots and a microschool's fast turnaround
  • 23:55 Why neither buyer likes pilots
  • 24:41 When onboarding falls apart after the sale
  • 26:50 What nobody tells you about being a principal
  • 29:00 What each wishes every vendor understood

About this episode

Joseph Dalton-Stark is the founding principal of Leadways, a second-year microschool in Cupertino, and the maker of an AI side project called Learner Mindset. Because the school started from nothing, he built its edtech from day one, and his year-one advice is blunt: avoid long-term lock-ins. Rather than sign a cheaper five- or seven-year deal, he worked from spreadsheets to feel out platforms and even started building his own, tailored to his families' feedback. His families work at Google, Meta, and Apple and are vocal about the tools they want in the classroom.

The middle compares how Joseph and John Faig, tech director at a private K-8, evaluate vendors. Joseph wants evidence he can see, video of people actually using a product, over a wall of percentages, while John thinks about compatibility with his single sign-on and systems, real impact, and service-level agreements. Both name the same tells that a vendor skipped the homework: generic language, pitching a trivial problem as if it's existential, talking district when the school is independent, and a district-sized price quote to a 30-student school.

On channels, cold email is mostly dead, but a warm, human LinkedIn message, referrals, and good timing get through, and both point vendors to study content marketing in other industries. They agree pilots don't work, Joseph decides after a short demo, John is against them outright, and that onboarding is where deals break, especially when every school onboards at once. Joseph's fix for AI pitches is to lead with how fast a team gets to full efficiency, not a five-year roadmap, and both close on the same ask: get the firmographics and priorities right, be authentic, and be there when something breaks.

Notable moments

We've got 30 kids. When somebody tells me a site license is $20,000 or $25,000, I look at them like they're absurd.
Joseph Dalton-Stark
The number one wrong thing is telling me how I'm going to fit into your system. I want to know what's going to positively impact us now, and how quickly you can support that.
Joseph Dalton-Stark

Questions this episode answers

How does a microschool buy edtech differently from a district?

A microschool like Leadways, about 30 students, moves fast and buys for its specific community. Joseph Dalton-Stark avoids long-term lock-ins in year one, works from spreadsheets to feel out platforms, and can decide after a short demo, where a district runs a longer, multi-stakeholder process.

Why do district-sized price quotes fail with small schools?

Because the math is absurd for the size. A $20,000 to $25,000 site-license quote to a 30-student school signals the vendor didn't research who they're contacting. Get the firmographics and the price to the school's scale, or the conversation ends immediately.

What do school leaders want instead of a five-year roadmap for AI tools?

Onboarding speed and near-term impact. A founding principal in year two isn't planning five years out; he wants to know how fast his team gets to full efficiency, what training and support come with the tool, and what will positively impact the school now.

Do microschools and private schools run pilots?

Generally no. Joseph Dalton-Stark does a short demo and decides within about two weeks; John Faig is against pilots entirely. Piloting one grade level produces skewed data, and if the pilot group likes a tool you don't adopt, you've burned a bridge.

What outreach actually reaches a microschool principal?

A warm, human LinkedIn message, referrals from peers, and good timing when the need is active. Cold emails mostly go unopened, default AI-agent DMs get ignored, and vendors who reflect back real understanding of the school earn a reply.

Peter0:04

Welcome to another episode of the K-12 EdTech Connection. We've got an awesome guest for you today. Joseph, can you give us some high-level context? You're the founding principal at Leadways School, and you also launched an AI-powered edtech company in the last year. How did you end up wearing both hats at the same time?

Joseph Dalton-Stark0:27

Thanks for having me on to talk about this. My school, Leadways, is in Cupertino, right in the center of the AI hub. Meeting with families, we're always talking about AI and the best tools, sharing tips and what we've been creating. Through that, I started making usable things, I've always been a tinkerer, I've been building stuff for years, but with AI where it is now, I've been able to build functional tools that other people found value in. It usually takes a little nudging to get me going, but someone said, you should share this, and that's how I birthed Learner Mindset. It's really a side project, though, 99% of my time is spent building Leadways, because it's a brand-new school.

Peter1:37

Leadways is in its second year, I believe. When you took the role, what existed and what didn't in terms of edtech infrastructure?

Joseph Dalton-Stark1:48

Nothing existed. I've been building it from day one, leaning on my previous experience. I'm a Google guy, so that was the easiest platform to jump into to get us started. The only business internet available at our site was Comcast, so we're shoehorned into certain things. But year one is really just picking and choosing.

Peter2:26

What would you tell other founding principals to avoid worrying about or spending on in year one?

Joseph Dalton-Stark2:35

The one thing I'd always avoid is locking yourself into a long-term commitment as a brand-new school. You're growing, meeting your founding families, learning their needs, and every community, every teaching staff, is different. It's tempting to sign one of those deals that are a lot cheaper when you buy five, six, seven years and really lock you in, but we stayed away from that. We worked with spreadsheets year one to feel our way through the platforms and decide where to go. What's neat is that turned into us developing our own platform for some things, tailored to us and our families' feedback.

Peter3:48

Given your location near Silicon Valley, is there anything different about catering to the families who send their kids to your school?

Joseph Dalton-Stark4:07

They're all very plugged in, because they work at Google, Meta, and Apple right down the road. They're mindful about the tools they use at home, and very vocal about what they want to see in the classroom. We're good at collecting feedback from students and families, and when we ask what they're looking for, they have a lot of great ideas that have pushed us forward in what we choose.

Peter4:48

John, switching to you, you're in a position where some vendor relationships go back years. How does that change what gets your attention when a new vendor reaches out?

John5:04

I appreciate somebody who understands my school's priorities and aligns with their value prop. More often than not, unfortunately, BDRs reach out to anybody with a pulse and don't understand the firmographics of my school or my priorities. Even if a relationship goes back years, I'd expect more from someone who's been along for the ride, as opposed to spraying and praying.

Peter5:42

Joseph, as a principal evaluating edtech, what's the first thing you look at when a vendor lands in your inbox?

Joseph Dalton-Stark5:55

Evidence and user experience. Numbers are great, but I love a good video, if you can show me how people are interacting with it or how it works, it helps me picture how I'd implement it with my staff or students. If I just get 40% here, 10% there, it doesn't click. You see it all the time in ads. I want to see people using it.

Peter6:30

John, same question flipped to you. When a vendor pitches you as the tech director, what's your filter?

John6:39

I'm thinking strategically about the whole infrastructure. I want compatibility with what I have, single sign-on, the student information system, other major systems. I'm looking for impact on faculty, staff, or parents, will it move the needle, or just be another login? And I look at service-level agreements, I want them to perform to our requirements and not leave us hanging if something goes wrong.

Peter7:09

For both of you, John first. Within the first 30 seconds of a vendor's email, pitch, or booth conversation, what are the tells that they haven't done their research on your role, school, budget, and priorities?

John7:30

Generic terms, not the words I'd use with a peer, and not understanding how important the problem is. A lot of people pitch me fairly trivial products as if that's my core problem. I've solved most of the big problems at my school; I'm looking to tackle new ones, but nothing's chronic. Don't pitch me as if my school will go away tomorrow if I don't buy your product.

Peter8:04

Joseph, what are the tells for you that a vendor hasn't done their research?

Joseph Dalton-Stark8:13

This one happens all the time: we're a microschool, an independent school, so when they start talking about your district, they missed their mark on the research somewhere. And the number one thing that gets me is price. When I ask what a site license looks like and someone says $20,000 or $25,000, I look at them like they're absurd. We've got 30 kids. I don't know why you'd even tell me that number. I'm hoping they've done enough research to know who they're reaching out to, so they're not wasting their time and mine on some ridiculously overpriced product.

Peter9:07

Can you walk us through the channels vendors actually use to reach you, cold email, LinkedIn, conferences, referrals, and what's getting through versus deleted?

Joseph Dalton-Stark9:21

I don't really open cold emails anymore. If it's something I've been actively looking for and it strikes gold in my inbox, I'll open it, but I get hundreds a day and I'm screening them out. I don't mind a good LinkedIn connection, though, as long as it's not the default AI-agent reach-out and you sound human, I'll probably engage. A lot of it is timing in edtech, is this something I'm struggling with and looking for right now? My eyes start seeing those things pop up in my inbox and my feed at the same time.

Peter10:14

So if someone has researched your school, goals, and priorities and can repeat those insights back to you, they have a better chance of your attention.

Joseph Dalton-Stark10:29

Definitely. It's the human part of sales. If I feel like you've invested time getting to know me, my student population, and my community, I'm more willing to give back and connect.

Peter10:47

Has a LinkedIn DM ever turned into a real conversation? What made it different?

Joseph Dalton-Stark10:55

Yeah, I have a few going right now about interesting technology partnerships. I'm very active on LinkedIn, I know some people hate it, but I'm posting, and it's a good connector for people searching for the same thing, whether it's a PBL app, student information systems, or AI. It works.

Peter11:33

John, thinking of cold emails, LinkedIn, conferences, referrals, and peer networks, how does that channel mix look different in your role?

John11:48

I rely on relationship channels. For me that's LinkedIn, I don't mind interacting in comments or getting a DM if we've had some relationship and I know who you are. I go to a few conferences, and I like the smaller ones. ATLAS was last week, the collective where independent-school tech directors meet once a year, and it's fabulous, a few vendors, integrated among us, not ISTE or FETC with a big vendor hall you brave at your own risk. I also don't mind a warm email from someone I talked to in previous years who says, you told me this wasn't a priority, is it now?

Peter12:59

John, on a previous episode you said that in 15 years as a tech director, not one sales rep has reached out proactively after switching companies or roles. What's that about?

John13:15

First, it could be me, full disclosure, I'm a self-directed purchaser and researcher, so maybe people don't think they need to keep up with me. But I've just never really had people keep up after they change jobs. More people leave the industry than move company to company; I've seen a couple change edtech companies, but it's the exception, not the rule.

Peter13:43

Joseph, you're a podcaster yourself and you build an audience. Does content marketing from the vendor side actually grab your attention, or is most of it noise?

Joseph Dalton-Stark14:03

It depends if it's unique. There's some content I don't interact with but I like seeing online, it's entertainment, really, and if I ever needed to move into those channels, they'd be first on my mind.

Peter14:25

Any specific vendor content that earned a click, a reply, or an outreach in the last year?

Joseph Dalton-Stark14:33

Shameless plug, because my wife works for them, but ServiceNow has been killing it on marketing. I've never engaged with her previous companies' content, but theirs is unique, and I'm super interested in AI agents right now, which is their angle.

John15:02

I'd encourage edtech companies to look at companies in other industries, because, to Joseph's point, people in marketing in other segments do a better job, maybe because they have resources. I find myself watching LinkedIn ads because there's a video or an animated GIF. So don't just learn from other people in edtech who might not be doing an amazing job; look at other verticals and watch what they're doing.

Peter15:37

Joseph, continuing John's thought on peer recommendations, how strong is that channel? Are you in principal networks where vendor names get passed around, good and bad?

Joseph Dalton-Stark15:51

Interesting, I don't see vendor names passed around too often unless someone specifically asks. It's rarely oh, I had a great experience with this company; it's more, this one fell through and I need something else, it's an emergency, who can help? But most of the companies we work with came through some referral, a friend over dinner saying, I just had a demo from this person and it was crazy, I'd love to connect you, they were blown away by the product and connected us.

Peter16:43

John, what about on your end, any tech-director networks?

John16:48

Honestly, those of us in the boiler room rely on peer networks more. I'm in a local DC-regional network of tech directors that's highly communicative, and a national group too. Between those I get a lot of information, not just what people think of vendors, but have you checked out this one? In some cases we've shared full tech stacks, we sent out a Google Sheet and people filled in every piece of software in their school. So if you want to know whether this product works with that one, we have a matrix of existing products, oh, you use this SIS with this LMS? Great, I need to talk to you.

Joseph Dalton-Stark17:45

John, I'm going to need that.

John17:48

Free of charge.

Peter17:51

Joseph, you told us what works for you as a buyer. On the flip side, have you used these same channels in your own outreach for Learner Mindset, or are different channels working?

Joseph Dalton-Stark18:09

Not much. For what Learner Mindset is right now, I haven't done much marketing or selling, it's all word of mouth. People find my website or see my posts and reach out. But thinking about the creative things I've seen online, there are so many unexplored avenues for both schools and edtech companies. We just launched a homeschool-connection piece to meet other families' needs, and it blew up, something I never thought of. I was reading online, does anybody have access to this app, or how do I track our learning online, and I thought, oh, we're building that, I wonder if we can reach out. A simple reach-out turned into a whole bunch of potential users.

Peter19:31

With your background building AI products for K-12, what are edtech vendors getting wrong about pitching AI tools to educators in 2026?

Joseph Dalton-Stark19:44

The number one wrong thing is telling me how I'm going to fit into your system. It needs to come from the other side: how quickly is my team going to get onboarded, and how quickly can we be running at 100% efficiency? I've had pitches, no joke, that go year one, year two, year three, year four, year five, you're going to be great. I'm in year two. I'm not thinking that far ahead. I want to know what will positively impact us now and how quickly you can support that. Come with a game plan: here's the training we do, here's how we support you, here are the resources. I need to see all that up front as a principal.

Peter20:42

John, does that resonate? Do you see that from vendors reaching out to you?

John20:49

A little. I encourage vendors to go where the buyers are, listen to what they're talking about, the wording they use, and understand how chronic the problem is. Particularly for young companies, focus on your ICP and anti-ICP, the two extremes, and nothing in the middle. A lot of people in education are just being cordial and nice, taking your time, and will probably never be a customer. In the short term, focus on the two extremes, the people leaning in and the people recoiling.

Peter21:33

A lot of vendors treat private K-8 schools as one homogeneous buyer. John, what's one assumption that falls apart when you compare your school and Joseph's side by side?

John21:50

The firmographics need to be accurate. Joseph made this point, I'm not a district or a large public school, I'm a medium-sized independent school in Washington, DC. Understand the firmographics before you talk to me. And it comes down to priorities: know what I'm working on this year. It's fine to ask, are you in the market for this, and if I say no, call me in 12 months, not earlier. Respect the ebb and flow of the school year. What rankles me is the person who checks in every month after I've told them it's not a near-term priority. I'm not saying I'll never buy; you just have to listen to what I'm telling you.

Peter23:04

Joseph, does a founding-stage school like Leadways pilot products, or is everything a full commit?

Joseph Dalton-Stark23:15

We don't really pilot. We'll do a short demo to get it in our hands and see how it works with some teachers, and we're pretty much ready to decide. If we were bigger, I've done it, you pick a grade level and have them use it over a semester. But our turnaround is about two weeks.

Peter23:46

In a previous episode John said he's a thousand percent against pilots. Joseph, your thoughts on pilots, free and paid?

Joseph Dalton-Stark23:55

I don't think they work. In a larger school, the grade level you piloted with is vastly different from the next one, so the data's skewed. And half your staff hates it anyway, or it doesn't work for them. It's a big waste of time. And if you don't go with it and the group you gave it to really liked it, you've burned bridges, because now they want it and can't have it. So I'd lean away too.

Peter24:28

John, has there ever been a case where you had a tool onboarded and something wasn't working after you bought it? What happens then?

John24:41

I'm proud to say we've never gotten far down that road before pulling the plug. We've pulled plugs early in implementation, when the onboarding didn't feel adequate, or things they represented in the demo didn't come to fruition, they overexaggerated the capabilities. Onboarding is critical because almost all schools onboard at the same time of year, so they need to staff up implementation specialists exactly when everyone else wants them. In this case, what they said didn't match what we remembered the product could do, and the implementation timeline stretched beyond the start of the school year, which most schools can't afford.

Peter25:52

Joseph, any demos where the red flags were apparent from the start?

Joseph Dalton-Stark25:59

Yeah, I've had demos where the person didn't know how to use the product. I don't take it personally, I think it's funny. Similar things, when they hand it to the staff and everyone's fumbling through it, you start weighing whether it's worth it. The biggest question for any edtech platform is, are your teachers going to use it to fidelity? If their first experience is that poor and it's that hard to use, they'll probably just ignore it in their classrooms, and then it doesn't help you.

Peter26:50

As we wrap up, Joseph, what's one thing about being a principal that nobody tells you ahead of time?

Joseph Dalton-Stark27:05

I got a good piece of advice once: handle the noise and focus on the silence. Every day you'll have an angry parent or an emergency at 10, at 2, at 6, and it's easy to get tied up in that. But if you focus on the silent pieces, the staff member who doesn't acknowledge you in the hallway, the kid who keeps their head down when you say hi, or, in data and edtech, the kids who don't show up in the reports because they're not on either end of the spectrum, that's where your culture is really built, not in the loud ones.

Peter28:02

John, anything about the reality of a tech director that nobody warns you about?

John28:09

I'd appreciate silence too. As I've said, I prefer vendors to build a relationship, be helpful, and be in the background, waiting for the opportunity. Ask me about my priorities, I know what I'm doing this year, next year, and beyond. Ask if it's a priority this year; if I say no, cool your jets and call me next year, great. But don't continually check in. Knocking on my door every month is disingenuous, it's not building a relationship, it's frying it.

Peter29:00

One more for you both, John first. What's one thing you wish every vendor understood about selling to your school?

John29:10

My priorities and the type of school I am, firmographics and priorities. If I'm not looking for a content filter, don't sell me one as if my school's imperiled without it. The worst is, hey, I was just talking with your neighbor's school, trying to gin up enthusiasm, that strikes me as juvenile. I know people in other verticals who built much bigger companies than edtech's, based on relationships, doing the right thing, and understanding schools' priorities and rhythms. They didn't bash down the door and stand outside waiting for you to open it all year.

Peter30:05

Don't use FOMO or the threat of discount pricing going away at year-end to rush the deal.

Joseph Dalton-Stark30:12

Right, sign up now. I'd say authenticity, same as John. When we're talking about making a deal, don't blow smoke, don't throw giant numbers at me to impress me. I don't care how many others you're working with, that you're in 400 districts or 12,000 schools. I just need to know if it works for me, and whether when I call because everything's broken, someone's going to answer and help us out. That's the relationship piece that matters in edtech.

Peter30:58

Thank you to all our listeners. Big thanks to my co-host John Faig, tech director at St. Patrick's Episcopal Day School, and our guest Joseph Dalton-Stark, founding principal at Leadways School in Cupertino, California. Thank you both.

Joseph Dalton-Stark31:17

Thank you, Peter and John.