🎙️ Why the Fastest “Yes” Beats the Biggest Budget — with Dr. Brooke Olsen-Farrell🎙️

January 11, 2026•5 min read

Let’s be honest. Every education founder has the same dream board.

You want New York City. You want LAUSD. You want Chicago.

You want the "Whales."

It makes sense on paper. One massive contract could clear your runway for two years. It looks great on a pitch deck. It feels like "making it."

But here is the hard truth:

Chasing the biggest districts is the fastest way to kill your company.

While you are navigating 18-month procurement mazes, getting passed between committees, and waiting for a budget cycle that might never align, your cash is burning. By the time a "Whale" is ready to buy, you might not be around to sell it.

Traction doesn't come from the biggest client. It comes from the fastest client.

In this week’s episode of The EdSales Edge, I sat down with Dr. Brooke Olsen-Farrell, a nine-year Superintendent at Slate Valley Unified School District and a National Policy Leader. We unpacked why the "Perfect Client" isn't a logo you brag about, it's a partner who actually buys.

Here is the detailed breakdown of why you need to stop chasing prestige and start chasing speed.

1. Speed is Oxygen (Why "Agile" Beats "Enterprise")

Large districts are like aircraft carriers. They take miles (and years) to turn.

Mid-sized districts – like Slate Valley – are speedboats.

Dr. Brooke explains that as a leader of a mid-sized district, she has the autonomy to make decisions fast. She can pilot a new tool next week. She can sign a contract without waiting for a six-month committee review.

For an early-stage founder, speed is oxygen.

A $20,000 contract that closes in 30 days is infinitely more valuable than a $200,000 contract that might close in 18 months. The smaller deal gives you cash flow, data, and a reference. The larger deal just gives you anxiety.

The Lesson: Stop vetting clients by their student population size. Start vetting them by their speed of decision-making.

2. The "Research Filter" (Why She Deleted Your Email)

Brooke opens her inbox at 7:00 AM. She sees dozens of cold pitches.

By 7:05 AM, she has deleted almost all of them.

She doesn't delete them because she's "too busy" to look at new solutions. She deletes them because they are lazy.

Most founders send generic "spray and pray" emails: “Dear Superintendent, we have a great solution for learning loss. Can we meet?”

Brooke uses a simple, binary filter to decide what gets opened:

"Did this person spend 5 minutes understanding my specific reality?"

If you reference her district’s strategic plan, a recent comment she made at a board meeting, or a specific demographic challenge unique to Slate Valley, you get opened. If you pitch a generic solution that could apply to any school in America, you get deleted.

The Lesson: Context is the key to the inbox. If you can’t find a specific hook that relates to her district, don’t send the email.

3. Co-Creation > The "Perfect" Pitch

Here is a psychological secret most founders miss: Superintendents hate being sold to, but they love being asked to lead.

When you approach a leader like Brooke with a finished, polished, "perfect" product, you are a vendor asking for money. You are putting them in a binary position: Buy or Don't Buy.

But Dr. Brooke revealed that she prefers to work with founders who want to co-create.

Instead of pitching a finished product, position your offer as a 90% solution. Say: "We believe this solves X, but we need a visionary leader to help us get the last 10% right for a district like yours."

This lowers resistance. It turns the conversation from a sales pitch into a strategy session. They aren't just buying a tool; they are shaping it to fit their ecosystem.

The Lesson: Stop pitching perfection. Pitch partnership.

4. The "Kingmaker" Effect (Unlock the Network)

You don’t need to win 50 districts one by one. That is the hard way.

You need to win one "Kingmaker."

Dr. Brooke isn't just a buyer; she is a National Policy Leader. She talks to Superintendents across Vermont and the AASA network constantly. They trust each other more than they will ever trust a salesperson.

When she finds a tool that works – and a founder who listens – she tells everyone.

One successful implementation in Slate Valley didn't just stay there. It rippled out to neighboring districts because Brooke became the Chief Evangelist for that product. She essentially became their Head of Sales for the region, without being on the payroll.

The Lesson: Focus all your energy on making your first few mid-sized clients wildly successful. Turn them into advocates, and let them unlock the state for you.

5. Your Size is an Asset, Not a Liability

Many founders try to hide the fact that they are early-stage. They try to look like Pearson or Houghton Mifflin.

Stop doing that.

Dr. Brooke was clear: Large publishers are often rigid, slow, and hard to work with. If a feature is broken, it takes a year to fix.

As a startup, your "smallness" is actually your competitive advantage. It means you are responsive. It means if she has a problem on Tuesday, you can fix it by Wednesday.

Leaders value partners who listen and adapt far more than they value vendors with a 100-year history. Don't apologize for being early-stage; sell the agility that comes with it.