Program Facilitator Jobs in Chicago, IL (NOW HIRING)

OVERVIEW:

Reporting directly to the Director of Central Program Delivery on the Central Program Team, the Program Facilitator is responsible for leading the design and delivery of program solutions that are on the vanguard of Year Up United's evolving program models utilizing centralized instruction and support. The Program Facilitator will be responsible for overseeing, designing, and delivering unique pilots that seek to connect Opportunity Youth to career-track jobs in rapidly scalable ways. The Program Facilitator is also responsible for driving and leading site-based projects that provide Year Up United with invaluable leverage and flexibility.

The ideal candidate will thrive in a fast-paced, dynamic, complex start-up, ever-changing entrepreneurial work environment. The candidate will be a strong and effective communicator who can expertly and independently navigate a variety of responsibilities, is comfortable with change, and can design and deliver training programs and solutions that achieve strong program outcomes. The candidate demonstrates strong facilitation and coaching skills and understands the principles of adult learning, how to effectively remove barriers to learning, and how to support and engage students in an open/flipped classroom environment.

To be successful in this role, you will be tech savvy and creative and brings expert communication, administrative, and management skills that serve as a model for participants and partners. The candidate can juggle multiplerelationships and a range of small and large-scale projects at once, has experience managing through influence, and can work collaboratively across internal and external stakeholders to ensure that all goals and metrics centered on student success are achieved.

In keeping with Year Up United's values, the Associate Director will have the opportunity to interact with students as coach, group facilitator, and advocate, participating in creating and sustaining a positive educational environment, with trust among students, faculty and site leaders.

KEY RESPONSIBILITIES:

Delivery Lead

• Work collaboratively with partners to ensure alignment across teams and coordinate support for students while ensuring that the needs of all parties are met
• Build and manage relationships with critical project stakeholders and drive a process to share information with the broader team on an on-going basis
• Develop programmatic materials and processes with an eye towards replication and scale across projects, teams, and markets
• Make programmatic decisions that meet the needs of both the students and employer partners
• Document program and participant-related data and synthesize/report out on trends and learnings
• Oversee additional program facilitators assigned to specific pilots and projects
• Represent the learning coach perspective when working with various functional teams
• Contribute insights, learnings and improvements to program pull ups/debriefs and support the development of improved systems for future program iterations

Learning Coach and Instructional Facilitator

• Ensure that Year Up United students are "graduate ready" upon completion of program through college-level and career-focused trainings conducted in all phases of the program for students:
  • Own and drive all aspects of teaching and assessing students in a twice-weekly "Career Development and Interpersonal Relations" course as student prepare to go on internship
  • Own and drive all aspects of teaching and assessing a once-weekly Internship Seminar for students as they transition from internships to career
  • Own and drive all aspects of the systematic delivery of skills-based seminars and courses for graduates of the program as they continue on their job search; including but not limited to topics such as: resume writing, job searches, interviewing techniques and make connections to higher education resources like FAFSA, grant/scholarship research, and college enrollment
• Ensure the accurate tracking of all metrics in a CRM (Salesforce.com) and LMS
• Support students' professional growth and development through thoughtful facilitation and coaching
• Provide check-ins and support structures that complement the student online learning experience
• Anticipate, identify and respond to student needs to provide high-quality services for students
• Provide regular updates on the status of the program and participants (highlights, retention challenges, issues to flag, etc.) to support student success
• Gather feedback of participant's progress and success to inform partners and Year Up United staff
• Develop and maintain relationships with other functional teams within the organization that are critical to serving students successfully

National Program Team Member

• Collaborate with Year Up United National and direct service teams to support projects and provide high-quality coaching support for students in their journey to achieve career readiness
• Support local program teams with general execution needs related to Year Up United's high support/high expectations model
• Provide regular updates on the status of the projects and participants, highlighting achievements, addressing concerns, and managing milestones with Year Up United National and direct service teams to ensure project success
• Develop materials with an eye towards replication and scale across projects, team and markets
• Other duties as assigned

• Live the values of Year Up United and integrate them into one's work on a daily basis
• Participate in initiatives that support the effectiveness, growth and impact of Year Up United
• Serve as student advisor/mentor, and participate in Learning Community with local sites

QUALIFICATIONS:

• At least 5+ years of experience in facilitating/teaching and coaching Opportunity Youth
• Proficient in case management documentation with skills in creating and executing support plans (MSW a plus)
• Experience creating virtual learning communities and coaching students by leveraging technology
• Experience designing, teaching, and facilitating workforce readiness curriculum and trainings with a commitment to asset-based adult learning principles
• Knowledge of job coaching, career counseling, job training and/or enterprise staffing requirements
• Experience as an advocate or case manager for historically underserved individuals
• Knowledge and understanding of crisis intervention protocols and modalities
• A professional and resourceful style with the ability to work independently and as a team player, to take initiative, and manage multiple tasks and projects at a time
• High comfort level in having one-on-one coaching conversations and facilitating difficult conversations withstaff and students alike
• Exceptional interpersonal skills with demonstrated experience in collaboration across diverse teams and geographic areas to solve complex problems effectively
• Proven ability to make good, proactive decisions in potentially emotionally charged situations and/or in the absence of complete clarity; comfortable taking risks
• Ability to handle sensitive and confidential information with discretion
• A passion for working with young adults, an unshakable belief in their potential
• Commitment to diversity and inclusion & Demonstrated experience working with diverse teams and engaging diverse groups of people with an understanding of the importance of cultural competency
• Proficiency with the Microsoft Office Suite, particularly Outlook and Word
• Understanding of the Opportunity Divide and its drivers

Salary Range:$70,500 - $82,000

WORKING AT YEAR UP UNITED:

Starting January 5, 2026, employees are expected to work on-site at least two days per week (Monday through Thursday dependent on job requirements). To be eligible for employment, candidates must live and work in a state (or an approved proximate state*) where Year Up United operates. For a list of eligible locations, please visit: https://www.yearup.org/job-training/locations

*Approved proximate states where Year Up United operates are: Connecticut, Indiana, New Hampshire, New Jersey, South Carolina and Virginia.

• Year Up United has established salary ranges for each of our sites, which allows us to pay employees competitively, equitably and consistently in different geographic markets. For roles in which the location is listed as flexible, the range displayed reflects the minimum and maximum target for new hire salaries for the position across all US locations. Salary offers take into account a candidate's skills, experience, and location. Your recruiter can share more about the specific salary range for your location during the hiring process.

• Benefits: Comprehensive healthcare options and dental coverage; 401(k) match for eligible participants.

• Vacation: Earn three weeks paid vacation in first year of employment; four weeks after initial year.

ORGANIZATION DESCRIPTION:

Year Up United is a national 501(c)3 workforce development organization committed to ensuring equitable access to economic opportunity, education, and justice for all young adults-no matter their background, income, or zip code. Employers face a growing need for talent while millions of talented young adults lack access to meaningful careers. These inequities only further perpetuate the opportunity gap that exists in our country-a gap that Year Up United is determined and positioned to close through three interconnected strategies: providing targeted skills training and connections to livable-wage employment for students and alumni; empowering others to serve and support young adults, and changing systems that perpetuate the opportunity gap. Year Up United's intensive training program utilizes a high expectations, high support model where students learn in-demand technical and professional skills and apply them during a corporate internship. Year Up United has directly served more than 40,000 young adults since its founding in 2000. Year Up United's nationwide presence includes Arizona, Austin, Bay Area, Charlotte, Chicago, Dallas/Fort Worth, Greater Atlanta, Greater Boston, Greater Philadelphia, Jacksonville, Los Angeles, the National Capital Region, New York City/Jersey City, Pittsburgh, Puget Sound, Rhode Island, South Florida, Tampa Bay, and Wilmington.

Voted one of the Best Nonprofits to Work For in the country by The NonProfit Times, Year Up United is a rewarding and impactful place to work. Our staff is passionate, supportive, mission-driven, and committed to positive change and continuous learning. We set high standards for both ourselves and our students and live by a set of core values that reflect an unshakable belief in the talent and potential of our young people. The work we do is life-changing, and we know that our team is the greatest asset in achieving our mission.

Year Up United 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. Learn more about our commitment to diversity: http://www.yearup.org/about-us/careers/commitment-to-diversity/
Year Up United 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. Please let our hiring team know if you need an accommodation at any point during the interview process. Information received relating to accommodation will be addressed confidentially.

Please submit a thoughtful cover letter and resume through our website.

We respectfully request no phone calls.