Why we're building Willow
(TL;DR: The system is broken, but it's fixable. We're helping 10 million students find their best-fit next step by 2033.)
A note from our
founder
My wife Liz is a pediatrician. Anyone who knows us well knows that I delight in drawing way too many comparisons between the challenges in our healthcare system and our education system.
In medicine, we don't just give a patient a “passing grade” and send them on their way; we measure what's working, and not. Yet, in education, we've spent decades focusing on the input (getting students into college) without enough honesty about the output (whether they actually graduate and find economic mobility).
I spent years leading charter schools, and I'll be the first to admit: I was wrong about a lot of things. I used to think a “college-for-all” mantra was the only way to ensure equity. But the data tells a different, more complicated story.
The challenge: a system in crisis
We have to be honest about the reality our students are facing:
The completion gap
85% of students from low-income households don't complete college by age 24.
The debt trap
There is currently $300 billion in debt held by 40 million people who didn't even finish their degree.
The underemployment trap
More than half of recent college graduates are underemployed a year after they finish school.
Quality college and professional programs can be life-changing. However, the inverse is true too. Dropping out with debt is the WORST outcome for young people. We have to be honest with our students about what programs are good, and which to avoid.
We've built a student success platform that cuts through the noise. Whether it's an apprenticeship, a certification, or a four-year degree, we help students find their best-fit, best-quality education next step.
The Willow solution: beyond “college vs. career”
At Willow, we don't believe in a “college vs. workforce” binary. It's about college, professional programs, and good first-jobs. Equity requires honesty about costs, outcomes, and quality.
ROI transparency
We provide personalized ROI projections so students understand the financial impact of their choices before they sign on the dotted line.
Comprehensive pathways
Our database includes 220,000+ verified programs, from traditional degrees to high-quality professional certifications.
AI-powered support
Our 24/7 career coach, Alma, ensures that no student has to navigate these massive life decisions alone.
Our progress (and where we're going)
We are a Public Benefit Corporation founded in 2023 with a “North Star” goal: Help 10 million students realize their full potential by 2033.
It's working. In our early pilots, students using Willow were 50% more likely to choose high-ROI programs compared to their peers. We're currently partnering with some of the most innovative schools systems in the country like Achievement First and DSST Public Schools to prove that when students have better information, they make better lives.
Join us in building a better map for the next generation. Onwards,

Meet the team
We're a group of educators, designers, and builders who believe the system is fixable.
James Cryan
Founder & CEO
The founder and former CEO of Rocky Mountain Prep, one of Colorado's most successful public charter school networks. James has almost two decades of experience as a public school teacher and leader.
LinkedInJaime Hudgins
Chief Academic Officer
Jaime brings over 17 years in education as a teacher, curriculum specialist, assistant principal, and Chief Academic Officer. She's led academics for a five-school network and scaled instructional practices nationally, and her deepest passion lives in future-focused curriculum—the work that helps students discover who they are and chart their own paths forward.
LinkedInLiz Wise
Quality Assurance & Operations
Liz has lived, breathed, and led successful school operations, with a focus on enrollment coordination, social media and quality assurance.
LinkedInRyan York
Chief Product & Technology Officer
Ryan has worked in education for 18 years as a teacher, instructional coach, principal, and charter school founder/co-CEO.
LinkedIn