EdTech sales is like playing telephone in a room full of people who speak different languages—the message gets more garbled with each handoff.
The person buying your product never uses it. The person using it has no idea why they have to use it.
And everyone in between is crossing their fingers they won’t get blamed when the whole thing crashes.
Won Ko learned this brutal truth when he jumped from traditional B2B software to EdTech, noticing the recurring challenge across education is that “there’s a lot of scaffolding and hierarchy.”
“Oftentimes, it’s the assistant superintendent who buys a particular product, but they are not the ones directly implementing it, and oftentimes, it gets passed down multiple levels where things get diluted.”
After two years of navigating this maze as our Senior Customer Success Manager, Won cracked the code for other EdTech implementation specialists. He built a systematic way to bridge these gaps while building relationships that survive the constant staff turnover plaguing public education.
Change When Good Tech Gets Lost
The promise of B2B sales is always seems so simple: clean handoffs and happy customers.
EdTech vendors love selling this fantasy.
But the ideal scenario is the tech person who buys your software is the same person who sets it up, trains everyone, and measures whether it works.
Won realized this is just how schools work—teachers focus on students and administrators handle purchases. It’s on EdTech companies to work around this reality instead of pretending it doesn’t exist. Or else it’s the students and teachers that end up being screwed over.
“Sometimes the assistant superintendent buys something,” Won explains, “and then passes it to the executive director, who hands it to the instruction director, who gives it to the curriculum coordinator.”
By the time your shiny platform reaches actual teachers, it’s been through more handoffs than a relay race where nobody knows they’re running.
Making things even more fun? Staff turnover happens faster than Marvel releases new superhero movies. Just when you think everyone’s on the same page, half your contacts have vanished to new districts.
As a result, teachers are staring at new software, wondering what they’re supposed to do with this digital mystery box that nobody bothered to explain.
Face Time > Screen Time
Won turned the traditional model upside down.
Instead of treating implementation like Amazon Prime delivery (drop it off and disappear), he treats it like building actual partnerships. Most EdTech companies, he observes, “sell something and [teachers] kind of have to figure it out by themselves.”
At Subject, we do the opposite.
We roll up their sleeves and get involved.
“We will spend the extra thousands of dollars and thousands of hours over the course of a school year to go on-site,” Won adds. This isn’t charity work or extreme customer service. This investment in face-to-face relationships creates partnerships built to last, while teaching Won intelligence he brings to every new district conversation.
The principle always remains the same: show up, do the work, build real relationships.
Change 4 Steps to Make Tech Work For Real Teachers
- Step 1: Map the Real Power Structure
Won starts by figuring out who actually makes decisions, versus who just thinks they do. It’s like understanding the difference between the person with the fancy title and the assistant who actually runs everything. “I try to multi-thread and build relationships with people who’ll probably be next for the job,” he says.
This means going beyond org charts to understand the human dynamics, and asking questions like:
- Who’s being groomed for leadership?
- Who do teachers actually trust?
- Who survives budget meetings without developing stress-induced eye twitches?
These are the relationships that matter when your original contact inevitably gets promoted, transferred, or decides to open that yoga studio they’ve been dreaming about.
His goal isn’t to become everyone’s best friend. Instead, he invests in relationships that stay solid even when administrators play their annual game of job musical chairs.
- Step 2: Gather Intel Like a Detective
Won combines hard data with actual conversations to understand what’s really happening.
“We’re looking at student data. How active are students? How sticky is our platform? Are we seeing good results?”
But he doesn’t stop at dashboard metrics.
The real insights come from walking the halls, talking to teachers, and observing what actually happens when nobody’s watching. It’s the difference between reading Yelp reviews and actually eating at the restaurant. Both matter, but only one tells you if the soup is actually hot.
This combination of numbers and narrative gives Won a complete picture that most competitors miss. While they’re celebrating login statistics, he’s discovering that teachers love the platform but hate the training materials, or students are engaged, but parents can’t help with homework because everything’s in English.
- Step 3: Create Custom Solutions That Actually Fit
Instead of forcing square pegs into round holes, Won builds programs around what districts actually need. “Based on what you’re telling me when I’m on site, you guys need help supporting English learners. Great, we have a separate program for that,” he explains.
This is where Subject’s modular design philosophy pays off. Rather than offering one giant solution that sort of works for everyone, they create specific configurations for different student populations—special education, English learners, credit recovery, after-school programs.
It’s like having a toolbox where you can actually find the right screwdriver instead of trying to use a butter knife because it’s the closest thing available. Teachers get tools that match their challenges, students get content that fits their needs, and administrators get results they can actually measure.
- Step 4: Turn Success Into Growth
When customized programs work, Won uses those wins to expand relationships and drive more partnerships. “When you show that versatility and establish rapport, it becomes easier to start asking for introductions to other people at the district.”
Success stories become the ultimate business cards. Instead of cold-calling superintendents with generic pitches, Won can say, “Remember how we helped your high school improve graduation rates? Let’s talk about what we can do for your middle schools.”
This creates a snowball effect where good outcomes lead to bigger partnerships, which create more good outcomes, which open doors to even bigger opportunities. It’s the rare business strategy that actually makes everyone happier—students learn better, teachers stress less, and administrators get results they can celebrate.
Success Stories Over Sales Pitches
The proof lives in places like Napa Valley, where Subject now operates in “every single high school—about 4 schools—plus two middle schools and lots of after-school programs.”
Numbers matter, but the most meaningful results come from listening to what’s happening in actual classrooms. It’s from the voices of teachers working with students every day that paint the clearest picture of success.
One teacher reports:
“Because of Subject, I feel like I’m connecting more with my kids. I have students actively reaching out to ask questions because they’re more engaged.”
When was the last time you heard a teacher say tech helped them connect better with students instead of creating more barriers?
The concern shouldn’t be about selling more software or hitting quarterly targets. The deeper purpose involves forging partnerships that remain strong despite the revolving door of administrators and ever-changing budgets. It’s about creating partnerships that survive staff changes, budget cuts, and the general chaos that defines public education.
And from Won’s four-step method proves that the best EdTech partnerships provide what schools need most: consistency.
With constant budget changes, staff turnover, and new initiatives, schools need reliable foundations to do their best work. That’s why it’s vital for these vendors to commit to being that steady foundation, so that teachers can focus on teaching and students can focus on learning.
The most radical thing you can do in EdTech isn’t building flashier software. Sometimes it’s just creating partnerships that remain solid no matter how many times the org chart gets reshuffled.