The $300K Lesson: Why Showing Up in April Means You're Already Too Late

Way back, early in my career, I lost a $300K deal in July.

• Not because the product wasn't a good fit.

• Not because the district didn't want it.

• Not because the committee didn't love it.

I lost because I missed the March School Board Meeting.

The curriculum director told me later: 

"We love this. But our budget was locked and board-approved in March. We can't add anything new next fiscal year."

That hurt. Because I thought I was early. I'd started conversations in April, given demos in May, and submitted a proposal in June. 

From my perspective, I was moving fast.

From their perspective, I was four months too late.

What I Didn't Understand About District Budgets

Here's what nobody tells you when you're starting in EdTech sales: district budgets don't run on company timelines. They run on fiscal cycles that start way before money actually gets spent.

I was operating on sales 101 basics—reach out, demo, close in 30-90 days. That works when you're selling to businesses with discretionary budgets and fast decision-making.

Districts don't work that way.

They have board approval processes. Budget committees. Procurement rules. Multiple stakeholders who need to weigh in. And most critically, fiscal calendars that lock months before the school year even starts.

I clearly didn't have a command of the buying or purchasing cycle. I do now. But hindsight is always 20-20.

If you're not in final conversations by March, you won't be in the budget come July.

I learned that the hard way.

The 18-Month Reality

After losing that deal, I had to figure out what "early" actually meant in K-12.

Turns out EdTech deals take about 12-18 months from first contact to signed contract.

Sure, you might get a deal quickly. But those tend to be exceptions, not the rule. Remember, even blind squirrels find nuts, too.

Here's the general breakdown for a typical July contract start:

October (9-12 months out) - Districts are figuring out what they need for the next school year. This is when you're building relationships and awareness. They're identifying problems, exploring options, and talking to peers. If they don't know you exist, you won't be considered.

January (6 months out) - Budget proposals are being written. Department heads are making their cases for what should be funded. This is when you need to be in active conversations with the people building those proposals. If you're not helping them articulate the need and the solution, someone else is.

April (3 months out) - Budgets have been finalized and approved by the board. If you're not already in the budget document, you're too late. At this point, the only changes being made are cuts, not additions.

July (contract start) - Contracts get signed and implementations begin. But the decision to work with you was finalized months ago. This is execution, not selling.

Most of us show up at month 3 and wonder why nothing's moving.

The deal was decided at month 6.

The Three Mistakes I See Founders Make

Now that I understand district budget cycles, I notice three patterns in founders who are struggling to close deals:

They're waiting for districts to reach out. Districts don't reach out. They're buried in their day-to-day operations. If you're not proactively building relationships, you're not on their radar when budget season arrives.

They're waiting for RFPs to drop. By the time an RFP is published, your competitor has already won. RFPs aren't the beginning of the buying process—they're the end of it. The district already knows who they want to work with. The RFP is just a procurement formality.

They're waiting for renewals to renew. If you're only talking to customers when it's time to renew, you've probably already been unseated. Your competitor has been in their ear all year, understanding their evolving needs, building relationships with new stakeholders.

When the budget's already set, it's too late.

What Changed for Me

Once I understood the timeline, everything about how I work changed.

• I stopped thinking in quarters. Started thinking in fiscal years.

• I stopped optimizing for "time to close." Started optimizing for "time to relationship."

• I stopped showing up with solutions. Started showing up with questions about what they're planning for next year.

Now I think about where each district is in their cycle. Are they in exploration mode? Budget planning mode? Approval mode? Implementation mode?

The answer changes what I do and when I do it.

If they're 12 months out, I'm not pitching. I'm listening, understanding their challenges, and becoming a resource they trust. Building awareness that we exist and can help.

If they're 6 months out, I'm helping them articulate the problem and the case for solving it. I'm connecting them with references. I'm making their job of building a budget proposal easier.

If they're 3 months out, I'm staying engaged and helpful, but I'm not expecting anything to happen. The budget is locked. My focus shifts to ensuring we're in next year's conversations.

If they're in implementation mode, I'm making sure they're successful. Because their success determines whether they expand, refer us to other districts, and renew when the time comes.

The Hardest Part

The hardest part of understanding district budget cycles isn't the knowledge. It's the patience.

Everything in startup culture pushes you toward speed. Move fast. Close quick. Show growth.

But districts don't move fast. And trying to make them move at your pace just makes you look like you don't understand their world.

I still mess this up. I still try to rush deals that are out of sync with budget cycles. I still want shortcuts that would let me close in 90 days instead of 18 months.

But when I match their pace instead of mine, things go better.

Conversations are more relaxed. Relationships are deeper. Trust builds naturally instead of 

being forced.

And when budget season actually arrives, I'm not scrambling to get in the door. I'm already in the room.

What This Means for You

If you're an EdTech founder struggling to close district deals, ask yourself:

When did you start the relationship with districts you're hoping to close this summer?

If the answer is "this spring," you're probably too late for this year. But you're perfectly positioned for next year—if you play it right.

1. Are you building relationships in October for budgets that will close the following March?

2. Are you helping districts articulate problems in January that get funded in April?

3. Are you staying engaged through the implementation so you're top of mind when next year's planning begins?

The founders who consistently win district deals aren't better at closing. They're better at starting earlier and staying patient.

They're building relationships in October for budgets that close in March and get spent in July.

It feels slow. Especially when you're being measured on quarterly metrics and investor updates.

But that's how districts work. And fighting against how they work just means you lose deals to competitors who understand the rhythm.

The Question That Changed Everything

Now, before I start working any district opportunity, I ask myself one question:

Where are they in their budget cycle right now?

• If they're 12 months out, great. We have time to build a real relationship.

• If they're 6 months out, good. We can still get into budget conversations if we move thoughtfully.

• If they're 3 months out, I know we're building for next year, not this year.

That one question saves me from wasting time trying to force deals that aren't aligned with their reality. And it helps me focus energy on the relationships that are actually in play.

District budgets don't run on corporate timelines.

The sooner you accept that and adjust your approach, the sooner you start winning deals.

Or you can keep showing up in April and wondering why nothing closes.

I did that and wouldn't recommend it.

Where are most of your prospects in the budget cycle right now? And what are you doing to match their pace instead of forcing yours?