How many sales courses have you taken over the past few years? How many frameworks did you learn? How many role-playing exercises did you do with a made-up district, a made-up administrator, and a made-up problem? And did any of those things actually help move deals forward in your pipeline? If you're being honest with yourself, the answer to that last question is probably uncomfortable. Not because the courses were bad. Not because you weren't paying attention. But because y

Every district has its own way of making purchasing decisions. The process depends on things like the district's size, what's being bought, and local politics. Because of this, the people involved can change from one situation to another. Still, one thing stays the same: there's always someone who understands the problem and someone else who can approve the purchase. These are usually different people. How you work with each of them decides if your deal moves forward or gets

Every founder I've worked with cares deeply about their product. They've spent years building it, refining it, and watching it make a difference for teachers and students. That passion is real, and it matters. However, that same passion can work against you when you're selling to a district. This is what usually happens: You believe in your product so much that you expect the district to see its value just like you do. You start by showing what it does, how it works, and why

Many EdTech founders think discovery is about gathering information. They go into a meeting, ask a few questions about the district's needs, take a few notes, and then move on to the presentation. Discovery done. But that's not real discovery. That's just going through a checklist. Real discovery is when your relationship with the district either begins to grow, or it doesn't. This is the moment when the administrator decides if you really care about their situation or if you

If you're an EdTech founder, there's a good chance you're getting meetings with school districts. You've built a product that works, you've got a story to tell, and you're able to get in front of the right people. That part isn't the problem. The real challenge comes after the meeting. You walk out feeling good. The administrator seemed interested. You showed them what the platform can do and answered their questions. They told you they'd be in touch. But a week goes by, then

I want to talk about the four words that kill more EdTech deals than bad products, bad timing, or bad presentations combined. “We don’t have money.” If you sell to K–12 districts, you’ve heard this before—probably more times than you’d like. Most founders I talk to handle it the same way: they thank the district administrator for their time, make a note to follow up next year, and move on. I’ve been selling into districts for 40 years. Senior roles at Pearson, HMH, and

Would you believe me if I told you your pipeline is fine? Rarely is it a pipeline problem. The problem is your sales process. You get meetings, give solid presentations, and send well-thought-out proposals. Then nothing happens. You follow up a few times, but eventually move on, thinking you need more leads. But if you add more leads to a broken sales process, you just get more ignored proposals and waste more time on deals that won’t close. The real issue is almost always yo

Not long ago, an EdTech founder could visit a district office, give a strong demo, share some pilot success stories, and rely on a good relationship with a curriculum director to close a deal. That approach no longer works. The K-12 EdTech market has changed, and many founders have not kept up. Budgets are tighter, oversight is stronger, and leaders have to justify every dollar to school boards and state agencies. Openfield’s researchers call this the “efficacy reckoning,” bu

I’ve spent 40 years selling to K-12 schools. I worked at Pearson, HMH, EPS Literacy & Intervention, and Matific before going full-time with my own consulting business. Over the years, I’ve seen the same thing happen again and again: founders with great products who can’t figure out why their deals keep stalling. They have conversations. Demos go well. District leaders seem interested. Proposals are sent. Then there’s silence. No rejection. No, “we went with someone else.” Jus

I ask every founder I work with a question that usually makes them uneasy. "If you disappeared for 30 days starting tomorrow, what would happen to your company?" Founders usually answer in three ways. Some quickly list all the problems that would get out of hand. Others hesitate and admit they don't know. A few say their team would manage just fine. The last group may not have the biggest companies, but they're building something that lasts. The Product Trap Most EdTech found

I've seen this happen countless times during my 40 years in EdTech. A company begins to gain traction. Revenue increases. They bring on salespeople, expand into new areas, and add some product features. Excitement builds. The board is pleased. The founder feels like they've finally figured it out. But after about 18 to 24 months, things start to change. Renewals decline. The sales team has trouble explaining why districts should stick around after the first contract. Leadersh

I got on a call with a founder a few weeks ago. Smart guy. Passionate about his product. His team was moving fast—demos every week, proposals going out, sales calls stacked back-to-back. But nothing was closing. "Mike," he said, "I haven't had time to actually think in three months. I'm just reacting." I've had this conversation more times than I can count in my 40 years in EdTech. Founders who confuse motion with progress. Teams that are busy but not productive. And t

I didn't know I was the problem until I wasn't anymore. For years, I operated under the idea that being a good leader meant being involved in everything. Every email that went out. Every meeting agenda. Every decision, big or small. I told myself it was about maintaining standards, but really? I just couldn't let go. The breaking point came on a Tuesday afternoon when I found myself in my fourth meeting of the day about font choices for a slide deck. I remember sitting there

I worked with a founder after they lost a multi-year deal. It wasn't a dramatic failure—no botched demo, no pricing mishap, nothing that would make for a cautionary tale at a conference. They lost it because they took too long to answer a superintendent's question. Five days. That's all it took for trust to quietly walk out the door. After four decades in this business, I've watched hundreds of deals succeed and fail. I've seen products win that probably shouldn't have, and b

A superintendent went quiet during one of my presentations. Not the bad kind of quiet. Just different. I was walking through our implementation process, showing timelines and explaining support structures. She stopped asking questions. Started nodding politely. The old me would've kept going. Finish the presentation and call it a win. Instead, I stopped. Reading the Room "What's on your mind?" Long pause. "My teachers are exhausted. I'm worried about adding one more thing, ev

I used to think good leadership meant knowing all the answers. Spent years proving I knew more than everyone around me. Made sure my team understood I was the expert. The result, I lost a lot of good people that way. The Pattern I Created Would give my team direction. Assume they understood. Get frustrated when they don't execute the way I expected. Focus on high-value opportunities. Target the right stakeholders. Prioritize likely deals. Made sense to me. It should've been o

A founder I worked with was drowning in his own business. Doing every sales call. Reviewing every proposal and contract. Answering every customer question himself. Kept saying: "I can't find anyone good enough to hire." Turns out that wasn't the problem. The problem was that every time someone on his team tried something, he took it back. Rewrote their proposals from scratch. Jumped on their calls. Overrode their decisions. His team gave up trying months ago. I told him what

Forty years in EdTech. I've watched a lot of companies come, and a lot of companies go. Most didn't fail because of bad products. They won a contract. Threw a party. Started chasing the next one. Meanwhile, the district they just signed was struggling. Teachers didn't know how to use it. Principals had questions. Nobody from the company is picking up the phone. When the renewal came around, the district said “no thanks.” The companies that are still around? They did it differ