James Cleveland

Chief People Officer

Interest Areas

Diversity & Inclusion
Recruiting & Company Strategy


James provides our clients a unique insider viewpoint into what it takes to build high-impact teams in ground-breaking education organizations. He has held leadership roles in a variety of positions, including strategic growth, fundraising, and operations and talent development at leading organizations.

Prior to joining Entangled, James served in C-level leadership roles at Reading Partners, College Track, Aspire Public Schools, and the Stupski Foundation, resulting in a 20+ year track record of achieving strategic growth through operations and talent development in nationally-focused education organizations. Additionally, James co-founded InsideTrack, a nationally recognized Student Success company, and was instrumental in growing Jumpstart, a national pre-K literacy organization, from 35 employees to over 200 employees and raising the organization’s value from $6 million to $18 million through his strategic and operational leadership.