Deputy Director, Career Pathways

Year Up • Chicago, IL

23h • Hybrid

About The Position

Year Up United’s National Team 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, Mid-Atlantic & Midwest Region, and Customer Experience Pathway plays a critical role in shaping and driving the success of Year Up United’s program strategy, regional operations, and academic excellence. This leader 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. The Deputy Director will oversee regional program leadership and performance across the following markets: Washington, DC, Chicago, Baltimore, Charlotte, Pittsburgh, Detroit. In addition, this role will oversee the academic strategy, instructional quality, and continuous improvement of the Customer Experience Career Pathway nationally, partnering closely with Academic Leadership, Learning Excellence, Career Services, Corporate Engagement, and Market teams to ensure that the curriculum aligns with evolving labor market needs and employer expectations. In this high-impact role, the Deputy Director will partner with cross-functional teams, including Enrollment, Corporate Engagement, Development, Technology, Career Services, Academics, Learning Excellence, Alumni, and Student Services, to ensure seamless alignment between strategy and operations. As a key member of the National Program Team, this leader will bring a data-driven, outcomes-oriented, and collaborative approach to achieving organizational goals. The Deputy Director plays a key leadership role in implementing Year Up United’s strategic vision across multiple markets and functions. This leader partners closely with Market Leaders, Senior Directors, and national functional leaders to support enrollment, program delivery, employer engagement, student success, academic consistency, internship success, and Full-Time Year Up job outcomes across the region and pathway. By leveraging data-driven insights, the Deputy Director identifies and implements enhancements that improve quality, increase efficiency, strengthen student and employment outcomes, and reduce costs without compromising standards. Working at the intersection of strategy and operations, this leader stays attuned to Year Up United’s evolving program model, technology roadmap, and labor market trends while fostering a high-expectations, high-support culture within and across teams.

Requirements

• 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.
• 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 Year Up United locations.
• Passion for Year Up United’s mission, a deep understanding of the Opportunity Divide, and a commitment to diversity, equity, inclusion, and belonging.

Nice To Haves

• Experience overseeing academic programs, instructional delivery, curriculum implementation, or career pathway strategy strongly preferred.

Responsibilities

• 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 to strengthen student outcomes, operational performance, and cross-functional collaboration.
• Understand the interconnectedness among enrollment, program operations, student services, academics, internships, career services, alumni, and corporate engagement, and facilitate alignment and resolve conflicts when needed.
• Maintain a deep understanding of the End-to-End Student Journey and leverage data insights to proactively identify challenges, improve operational effectiveness, and enhance the student experience.
• Steward and execute annual strategy plans and priorities, including enrollment growth, program delivery evolution, operational optimization, and outcomes improvement.
• Coach and develop regional and pathway leaders to support strong execution, leadership growth, and organizational alignment.
• Create and sustain a team culture of high expectations and support rooted in Year Up United’s core values and leadership behaviors.
• Oversee the academic strategy, instructional quality, and continuous improvement of the Customer Experience (CX) Career Pathway nationally.
• Partner with Academic Operations, Learning Excellence, instructors, and pathway leaders to ensure curriculum remains aligned with labor market trends and employer expectations.
• Support consistent instructional standards, learner experience, and pathway execution across markets.
• Collaborate with Corporate Engagement, Alumni, and Career Services teams to strengthen alignment between curriculum, internship opportunities, and full-time employment outcomes.
• Monitor pathway-specific performance indicators, including student retention, internship conversion, employment outcomes, satisfaction, and pathway effectiveness.
• Help shape future pathway innovation and evolution informed by workforce trends, technology, AI, and changing employer skill needs.
• Promote national best practices and continuous learning across CX pathway teams and instructional staff.
• Drive the execution and evaluation of all programmatic activities and student services across the region.
• Support alignment of training programs with labor market needs, ensuring students are equipped for successful transitions to internships and long-term careers.
• Maintain a strong understanding of employer partner needs, hiring trends, and workforce demand across the region and the Customer Experience pathway.
• Partner with functional leaders to create structured feedback loops that integrate employer insights into program and curriculum enhancements.
• Monitor program outcomes, including enrollment, retention, internship attrition, satisfaction, graduation, internship conversion, and Full-Time Year Up employment success, implementing strategies to address areas for improvement.
• Support implementation and optimization of hybrid program delivery models and evolving instructional strategies.
• Leverage Career Pathway expertise and national best practices to promote collective learning and operational consistency across markets.
• Oversee operational efficiency by implementing best practices and leveraging technology to enhance program delivery and decision-making.
• Utilize Salesforce, Tableau, matching systems, analytics, and other reporting tools to reinforce data-driven decision-making and operational consistency.
• Lead change management efforts by guiding teams through new practices, operational standards, technologies, and organizational initiatives while preserving Year Up United’s mission-driven culture.
• Identify opportunities to improve operational efficiency, reduce cost-to-serve, and streamline processes while maintaining high-quality student experiences and outcomes.
• Support regional budget management by reviewing financial performance, understanding variance drivers, and identifying cost efficiencies without compromising program quality.
• Support the execution of in-person learning and engagement standards across all regional markets.
• Understand the capabilities and economics of enrollment, program delivery, matching, placement success, alumni engagement, and career services, and actively identify opportunities to improve scalability and operational effectiveness.
• Strengthen relationships with academic institutions, community colleges, corporate partners, workforce organizations, civic leaders, and donors across the region.
• Represent Year Up United externally at workforce development convenings, employer meetings, and community engagements.
• Enhance Year Up United’s brand and market presence by positioning the organization as a leader in workforce development and talent strategy.
• Serve as a visible leader across the region and Customer Experience pathway, inspiring confidence and trust through collaborative, mission-driven leadership.
• Identify and pursue regional growth, partnership, and innovation opportunities aligned with organizational priorities.
• Participate actively in Year Up United’s Learning Community by facilitating group sessions, mentoring students, and contributing to a positive educational environment.
• Provide thought leadership to advance organizational learning and national best practices.

Benefits

• Comprehensive healthcare options and dental coverage
• 401(k) match for eligible participants
• Earn three weeks paid vacation in first year of employment; four weeks after initial year.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed