Chief Executive Officer

at TRAILS

The Organization

Summary: Hailed by former director of the National Institute of Mental Health, Tom Insel, as “the best evidence-based model we have for K-12 mental health services in the United States,” TRAILS is on a path to national impact, having reached 500K students and 25K educators, fueled by $60M in public funding and $12M in private philanthropy.

The current landscape: As they look toward major national expansion, TRAILS is making a move that’s rare within the nonprofit sector, pivoting to a nimbler team and advancing a technology-enabled product. These shifts are designed to drive down costs and generate earned revenue as a major funding stream, while simultaneously creating a better user experience and a more scalable impact.

> TRAILS

The Role

WHAT YOU WILL ACCOMPLISH

LAUNCH

TRAILS’ new economic model and go-to-market strategy, establishing a suite of best-in-class products with optimal market fit and scalable distribution channels.

DEVELOP

a new organizational culture centered on meeting customer needs, driving results, and ensuring long-term sustainability.

DRIVE

revenue through CEO-led partnership cultivation and sales; and by building upon TRAILS national reputation of excellence

A MONTH IN THE LIFE

WHO SHOULD APPLY

Chief Executive Officers
Executive Directors
Chief Operating Officers
C-Suite Leaders
EdTech & Startup Leaders
Entrepreneurs with Go-To-Market experience
Revenue Strategists
Change Managers

WHEN/WHERE/HOW MUCH

Start date: Winter 2026
Location: Remote
Salary range: $290,000 - $315,000 plus benefits

POSITION REPORTS TO
The TRAILS Board of Directors

APPLICATION DEADLINE
Monday, December 1, 2025, at 11pm ET

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WHAT STAKEHOLDERS SAY

“TRAILS is exactly what schools need. It pairs professional development training with comprehensive support and a full library of resources – building a common language across all three tiers.”
- Jenny Wakeman, Assistant Superintendent, Colorado

KEY STAKEHOLDERS