Deputy Director, Career Pathways

Overview

Deputy Director, Mid-Atlantic & Midwest Region and Customer Experience Pathway - Year Up United  seeks an experienced, visionary leader to oversee program quality, operational excellence, student outcomes, and market leadership across the Mid‑Atlantic and Midwest Region, while also providing leadership and oversight for the Customer Experience (CX) Career Pathway academics nationally.

Reporting to the Chief Operating Officer, the Deputy Director will shape and drive the success of Year Up United ’s program strategy, regional operations, and academic excellence. The role is accountable for achieving key metrics, outcomes, and performance indicators (KPIs) while fostering excellence in program delivery and ensuring strong cross‑functional collaboration across the student lifecycle.

Regional Leadership, Operations Management, and Team Development - Serve as the senior program leader for the Mid‑Atlantic and Midwest Region, ensuring alignment with organizational priorities and consistent execution across markets; partner closely with Market Leaders and functional teams; maintain a deep understanding of the End‑to‑End Student Journey and leverage data insights; steward annual strategy plans; coach and develop regional and pathway leaders;

create a team culture of high expectations.

Customer Experience Pathway Academic Leadership - Oversee the academic strategy, instructional quality, and continuous improvement of the CX Career Pathway nationally; partner with Academic Operations, Learning Excellence, instructors, and pathway leaders; monitor pathway‑specific performance indicators; shape future pathway innovation; promote best practices.

Program Excellence and Delivery - Drive execution and evaluation of all programmatic activities and student services across the region; support alignment of training programs with labor market needs; partner with functional leaders to integrate employer insights; monitor program outcomes; support hybrid delivery models and instructional strategies; promote learning across markets.

Operational Excellence and Financial Management - Oversee operational efficiency by implementing best practices and leveraging technology; lead change management; identify opportunities to improve efficiency; support regional budget management; maintain in‑person learning standards; understand economics of program delivery.

Market Leadership and External Engagement - Strengthen relationships with academic institutions, corporate partners, workforce organizations, civic leaders, and donors; represent Year Up United  externally; enhance the brand; pursue regional growth and partnership opportunities aligned with priorities.

Learning Community Member - Participate actively in Year Up United ’s Learning Community; facilitate group sessions; provide thought leadership.

• Minimum of 8–10 years of leadership experience with increasing scope and responsibility, including managing senior leaders and cross‑functional teams.
• Demonstrated experience leading complex, multi‑site, growth‑oriented organizations or programs.
• Experience in workforce development, education, nonprofit leadership, or related fields.
• Experience overseeing academic programs, instructional delivery, curriculum implementation, or career pathway strategy strongly preferred.
• Strong understanding of labor market trends, employer engagement, and workforce readiness.
• Proven ability to develop and execute strategic plans, manage change, and align resources to organizational goals.
• Expertise in program delivery, operational excellence, data analysis, and continuous improvement.
• Familiarity with Salesforce, Tableau, and analytics platforms to support data‑driven decision‑making.
• Strong budget…