Deputy Director, Career Pathways

Year Up, Inc; Chicago (IL); Hybrid; USD 160,000 - 190,000; Full time

Benefits offered by this job

Comprehensive healthcare options

401(k) match

Three weeks paid vacation

Job summary

Year Up, Inc is looking for a Deputy Director for the Mid-Atlantic and Midwest Region, responsible for overseeing program quality, operational excellence, and student outcomes. This leadership role requires a visionary leader to enhance market leadership and ensure exceptional delivery across the region.

The ideal candidate will have at least 8-10 years of progressive leadership experience, a strong understanding of workforce development, and a commitment to diversity and inclusion. A competitive salary range of $160,000 – $190,000 is offered along with comprehensive benefits, including healthcare options and paid vacation.

Qualifications

• Minimum of 8-10 years of leadership experience with increasing scope.
• Experience overseeing academic programs or curriculum implementation.
• Strong understanding of labor market trends and workforce readiness.

Responsibilities

• Oversee program quality and operational excellence.
• Drive execution of programmatic activities across the region.
• Strengthen relationships with academic institutions and corporate partners.

Skills

Leadership experience

Operational excellence

Program delivery

Financial acumen

Empathy and collaboration

Education

8-10 years of leadership experience

Experience in workforce development

Tools

Salesforce

Tableau

Job description

Overview

Deputy Director, Mid-Atlantic & Midwest Region and Customer Experience Pathway - YearUpUnited 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 YearUpUnited’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.

Key Responsibilities

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 YearUpUnited externally; enhance the brand; pursue regional growth and partnership opportunities aligned with priorities.

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

Qualifications

• 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 management and financial acumen with a focus on operational efficiency and quality outcomes.
• Demonstrated ability to lead with empathy, accountability, transparency, and collaboration.
• Experience working in a cross‑cultural organization diverse in race, gender, and ethnicity.
• Willingness to travel approximately 20–30% across YearUpUnited locations.
• Passion for YearUpUnited’s mission, a deep understanding of the Opportunity Divide, and a commitment to diversity, equity, inclusion, and belonging.

Salary & Benefits

Salary Range: $160,000 – $190,000

Benefits: Comprehensive healthcare options and dental coverage; 401(k) match for eligible participants. Vacation: Three weeks paid vacation in the first year of employment; four weeks after the first year.

Exempt role (paid on a salaried basis).

Location & Work Arrangement

Starting January5,2026, employees are expected to work on‑site at least two days per week (Monday through Thursday depending on job requirements). Candidates must live and work in a state (or approved proximate state) where YearUpUnited operates.

Approved proximate states: Connecticut, Indiana, NewHampshire, NewJersey, SouthCarolina, and Virginia.

Commitment to Diversity

YearUpUnited embraces diversity and equal opportunity in a serious way. All aspects of employment, including the decision to hire, promote, discharge, or discipline, are based on meritocracy. We do not permit discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristics protected by federal, state, or local laws. YearUpUnited is also committed to working with and providing reasonable accommodations to individuals with disabilities. Your recruiter can provide details regarding the expected work environment and any physical requirements. Information received relating to accommodation will be addressed confidentially.