Linda Haitani—

THE STORY

How I got here, in three chapters.

I've used the em dash in my writing for as long as I can remember — well before it became one of the most famous tells of AI prose. It's not a style choice. It's the punctuation of transition. There's a thing, and then there's a next thing — and the em dash is the moment between them. That's the shape of the work I've been doing for two decades, and three chapters of it stand out.

Ravenna

I co-founded Ravenna Solutions and led it as CEO. I started the company because I could see what was coming for K-12 private schools. The internet was about to reshape how schools worked, and admissions was where the reshaping would land first. Admissions at the time was all paper and file folders, hand-tracked, mostly invisible to the institution itself. Ravenna moved private school admissions online at scale across the independent school market — but the more durable contribution came after the digitization. The data we were now capturing could be turned into insight: about enrollment, about financial planning, about how a school's own funnel actually worked. For most schools, it was the first time they'd seen that picture.

NAIS and Clarity

After Ravenna, I joined NAIS. My work there centered on technology innovation across the independent school market, with an emphasis on data — including the financial scenario modeling tool NAIS distributed to member schools during COVID. We built it for heads of school and business officers in a moment when historical data had stopped being a reliable predictor of anything. They needed a way to think through scenarios that weren't extrapolations from the past.

From NAIS, I moved to Clarity. I worked in-the-trenches on financial aid, enrollment contracts, and billing — leading sales and marketing while advising on financial planning and product roadmap. The work took me into private school business offices over and over.

CEO Advisor

Alongside all of that, I've kept working with early-stage edtech companies as a CEO advisor. I love the chaos of early-stage work. The financial decisions are consequential, and they get made without historical baselines to lean on. The scenario thinking and qualitative judgment that substitute for time-series data — that's what early-stage operators do every day. Those are exactly the instincts private schools now need.

AI is the next transition. The decisions leaders are making, the institutional questions behind them, the leadership work itself — these aren't new in shape. What's new is the instrument and the speed of the cycle. The warrant for what I'm writing here is the same one that has organized my work for twenty years.