Imagine this: Your district treats EdTech procurement like ordering from McDonald’s—check the menu, pick the least-terrible option, hope it doesn’t give everyone food poisoning.
Ana Romero watched this tragic comedy play out from both sides of the equation. She spent years wrangling kindergarteners through Spanish immersion at Lompoc Unified, then transitioned to Chief of Staff at Subject, where she encourages districts to order “off-menu.”
Her dual perspective revealed something crucial: you have way more negotiating power than you think.
Romero notes that a lot of education leaders may underestimate the influence they have when dealing with vendors.
“Educators should know that they’re able to negotiate.”
EdTech companies—especially startups—are desperately hoping for feedback from real classrooms to improve their offerings.
Districts assume they have to accept whatever exists. Companies assume districts don’t want custom solutions. Meanwhile, classrooms get stuck with tools that almost solve their problems.
The smart money is on education leaders who figured out how to flip this entire dynamic.
Schools Give Away Their Best Stuff for Free
Walk into any district procurement meeting and witness the same ritual: administrator sees the price, does quick math, realizes it’s double their current solution, and shuts down faster than a teacher’s laptop running Windows Vista.
“They can immediately see a sticker price and immediately go ‘Nope, not gonna happen. This is two times as expensive as what I’m currently using,'” she explains. (Excel budget sheets don’t lie…though they do judge your life choices silently.)
But this sticker-shock reaction misses what’s actually happening in the market. Districts don’t realize they’re sitting on something more valuable than their annual technology budget: authentic classroom insight that helps companies build products people actually want to use.
Think about it. Every EdTech startup is trying to crack the same puzzle: how do you build something teachers won’t abandon after two weeks? They need districts who can tell them why Platform A collects digital dust while Platform B becomes part of the daily routine.
“We meet so many educators who won’t even ask questions because they immediately assume we’re not going to be able to do it,” our chief of staff adds. This learned helplessness costs districts the possibility of custom features, better pricing, and solutions designed around their specific challenges.
The irony runs deeper. While districts treat EdTech companies like immovable objects, these same companies often have no clue what actually works in classrooms. They’re building based on best guesses and competitor analysis, not real feedback from people managing 30 teenagers after lunch on Friday.
Startups particularly need this relationship to survive. They can’t afford to build the wrong thing twice.
What’s at stake? Districts that maintain traditional vendor relationships get whatever the market decides to build. Those that establish true partnerships? They influence what gets built next.
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How to Boss Vendors By Each Quarter
The districts winning this game operate on the same rhythm as their strategic planning: quarterly cycles that align vendor development with district goals.
Forget annual contract renewals followed by radio silence. Partnership relationships create ongoing dialogue that actually benefits both sides.
- Q1: Assess and Align
Partnership starts with brutal honesty about what’s actually broken and which vendors might help fix it. (It’s probably everything.)
“You have a lot of leverage in letting us know what you need built,” Romero says, referring to districts. “I’m going to come back to you every quarter, and I’m going to ask you what are your new goals and your new initiatives.”
This is all about collaborative product development rather than “customer service theater.”
The key insight here is that not all companies can build custom features. You need to distinguish between vendors offering genuine partnership and those locked into rigid product roadmaps. (Hint: if they can’t explain their development process, they probably don’t have one worth partnering with.) - Q2: Request and Refine
Month three brings the first major test: does this vendor actually listen, or do they disappear?
The difference between a vendor and a partner is that one disappears and the other delivers. True partners don’t vanish after contract signing like a bad eHarmony match. They actively seek feedback on features in development *before* those features get locked in stone.
“We’ll even do live product sessions and say, ‘this is what our team is currently building. Can we get your thoughts and feedback on it?'”
Districts discover their influence extends beyond current features to future product direction. “Who knows? I might be hearing the same things down the street,” Romero says, referring to the possibility of a widespread need.
Translation: your feedback helps vendors realize which features can benefit multiple schools and districts. Everyone wins. - Q3: Review and Measure Impact
Mid-year brings progress evaluation and relationship calibration. By mid-year, teachers have spent enough time in the platform to spot exactly where it breaks down—and smart vendors want to hear about every glitch, workflow hiccup, and ‘why can’t this thing just…’ moment.
This is where the impact becomes visible. “They feel like they’re an actual thought partner. And they are—we actually do take their feedback, but they feel like they’re part of the building process.”
Districts that initially felt hesitant about making requests become comfortable advocating for their needs. “You can see throughout the year that they actually become really good at emailing and being very vocal with their needs and their asks.” - Q4: Plan and Renew
Year-end planning extends beyond contract renewal to strategic partnership evaluation. Which relationships delivered genuine value? Which vendors proved capable of building custom solutions versus those that offered empty promises?
The quarterly cycle creates accountability on both sides while ensuring vendor relationships align with evolving district priorities rather than becoming stagnant annual obligations.
It’s strategic planning, not vendor management.
Being Picky Pays Off
The education technology market is shifting toward companies that can build authentic relationships with districts, rather than those that simply deliver standardized products. (About time, honestly…)
Teachers know immediately when something is off. Students are expressive, whether communicating their thoughts directly or shutting down with boredom. At the same time, district administrators and other school leaders focus on implementation outcomes and budget impact rather than daily platform navigation.
“When you find these companies are building quickly, don’t be afraid of asking them to do things and to build things for you, because they have the ability to do so.”
Districts willing to work with newer companies benefit from their flexibility. “You’re not going to be calling a 1-800 number,” she adds. “We are a startup, and you almost have to explain to them what a startup is.” Pro tip: if you have to explain what a startup is, you’re probably talking to the right people. (Think of it as the difference between asking your tech-savvy nephew for help versus calling Geek Squad.)
Education is not a one-time transaction. EdTech vendors should treat educators as the experts, and actively engage with their feedback to build a sustainable partnership.
Your Cheat Sheet for Better Deals
- Start with Pain Points, Not Features
Walk into vendor meetings asking the right questions. “Currently, right now, what are areas of improvement? If you had a magic wand and you could get your current platform to do anything, what would that be?” Most districts jump straight to price comparisons without identifying what actually needs fixing. - Understand What Kind of Company You’re Dealing With
There’s a massive difference between calling a 1-800 number and working with a startup that can build custom features in months, not years. “You’re not going to be calling a 1-800 number. We are a startup, and you almost have to explain to them what a startup is.” Ask vendors about their development process and timeline for custom requests. - Build Relationships at Every Level
Include teachers and principals in vendor evaluation from day one. Their feedback becomes ammunition for better deals while ensuring successful adoption. Districts that skip this step end up with expensive platforms nobody uses. “If you don’t have the principal and the teacher buy-in at the site level, that adoption is not going to happen as quickly as you’d like.”
Because nothing kills a great EdTech partnership faster than teachers who refuse to use it.
Your district doesn’t have to keep accepting whatever vendors decide to build.. You’ve got the quarterly framework, you understand your hidden leverage, and you know your classroom feedback is worth a fortune.
Ana Romero realized educators do the best QA testing—they just never get paid for it. She’s helping districts enhance engagement, retain enrolled students, and boost graduation rates because she knows that education leaders have way more power than they think. The districts that learn this first will get custom features, better pricing, and partnerships that actually work.
Your next vendor meeting is coming up. So, it’s time to stop asking “What do you have?” and start asking “What can you build?”