Manager, Apprentice & Employer Success

ORGANIZATIONAL OVERVIEW

CityWorks DC’s mission is to dramatically improve the early career outcomes of DC youth and young adults by creating innovative programs and by mobilizing employers, educators, and city leaders to create a local, diverse talent pipeline. Our vision is that all young people in DC have the “social mobility trifecta”: 1) valuable certifications and credentials; 2) paid, relevant work experience; and 3) a supportive professional network. To provide this trifecta to all youth, especially those who are marginalized and historically overlooked, CityWorks DC focuses its work on redesigning how young people experience high school, postsecondary, and early employment into multiple pathways to high-wage, high-demand careers. To accomplish this bold vision, CityWorks DC’s theory of change has two complementary strands: 1) launch a targeted set of innovative programs that work directly with young people; and 2) lead citywide initiatives designed to create lasting change in our education and training systems for DC youth.

Run by CityWorks DC, CareerWise DC is an industry-led, youth-centered, modern youth apprenticeship program that bridges classroom and on-the-job learning to provide flexible pathways to economic mobility. CareerWise prepares youth and young adults in the DC region for competitive, high-wage careers in fields such as business operations, information technology, finance, and—most recently, in 2025—healthcare.

JOB OVERVIEW

The Manager of Apprentice & Employer Success plays a central role in delivering a high-quality apprenticeship experience for both youth apprentices and employer partners. This position serves as the primary point of contact for employer partners, ensuring seamless onboarding, consistent program support, and long-term engagement. The Manager supports apprentices’ success by aligning training plans with workplace learning and providing coaching throughout the apprenticeship experience to ensure their retention and program completion. The Manager also supports apprentice recruitment activities during peak recruitment season, as well as additional special projects.

This is a highly collaborative, relationship-driven role ideal for someone passionate about youth career development, employer engagement, and building equitable pathways to economic mobility. We’re seeking an agile and client-oriented leader with excellent interpersonal skills who can quickly build trust with assigned employer partners and apprentices. The Manager of Apprentice & Employer Success embodies our values (Excellence, Innovation, Equity, Youth-Centered, and Collaboration) daily and embeds them into their work. The Manager will thrive in a dynamic and highly collaborative team—we communicate regularly, pivot quickly based on real-time learning, and jump in wherever our skills are needed.

This full-time position reports to the Director of Program and Partnerships and collaborates closely across the CityWorks DC team. CityWorks DC operates in a hybrid working environment, with in-person attendance at our Washington, DC office required one day/week and additional, regular in-person responsibilities required at sites across DC and Northern Virginia for programmatic activities, partner support, team planning and retreats, and other organizational events. In general, 30-50% of this role will require being onsite, in-person, depending on the program cycle. No relocation funding will be provided. Strongly preferred start date is August 4, 2025.

RESPONSIBILITIES

Employer Partnership Management – 40%

• Serve as the primary relationship manager for a portfolio of employer partners, providing regular support via monthly check-in calls and proactively addressing apprenticeship challenges to ensure quality outcomes for the employer.
• Lead the onboarding of new employer partners, including occupation alignment, job description creation and posting, and application system training for hiring managers.
• Manage the hiring process with employer partners, including monitoring candidate applications, coordinating interviews, and supporting hiring managers with hiring steps.
• Provide thoughtful and responsive partnership support and high-quality customer service, applying a problem-solving mindset and recognizing equity and scalability as key elements for all recommended solutions.
• Collaborate with apprentice supervisors to develop and monitor occupation-aligned training plans and upskilling experiences.
• Support the design and implementation of supervisor training and professional development to ensure high-quality apprentice supervision and engagement.
• Support Director and Senior Manager with partner expansion efforts during partnership renewal cycles.

Apprentice Support & Program Implementation – 40%

• Ensure seamless operations and logistics for hired apprentices, including transportation plans, pre-hire requirements, scheduling, work permits, onboarding paperwork, etc.
• Establish a monthly check-in cadence with assigned apprentices to provide direct support and coaching to apprentices during the entire apprenticeship lifecycle, identifying and addressing challenges through proactive communication and support, and guiding apprentices through post-secondary planning as it relates to the apprenticeship.
• Monitor apprentices’ progress on program completion benchmarks and training plans, proactively addressing any barriers to success.
• Support the design and implementation of apprentice professional development and occupational training sessions throughout the year.
• Assist with apprentice recruitment and application support efforts during peak hiring season, ensuring a strong match between youth interest and employer needs.

Data Tracking, Technology Management, and Program Administration – 20%

• Collect and manage key apprentice and employer partner forms, including W-9s, invoices, apprentice program agreements, registered apprenticeship forms, etc.
• Maintain accurate and timely data in Salesforce, Monday.com, and other tracking systems, and ensure tech is working smoothly for CityWorks DC staff and other stakeholders.
• Manage the collection of apprentice and supervisor data, including semi-annual competency evaluations, quarterly on-the-job and related instruction hours, and other key data.
• Draft and distribute relevant communications, including newsletters, updates, and event promotions.
• Support data reporting for annual KPIs, program goals, grants, and organizational learning.

QUALIFICATIONS

• Deep commitment to achieving racial equity and the belief in the promise inherent in all people
• 3-5 years of relevant work experience in relationship management, client services, youth program coordination, workforce development, and/or a related field
• Polished client management skills; high level of composure and confidence in meetings with senior leaders in businesses and state agencies
• Prior experience working directly with youth, and track record of building rapport with and influencing youth in the secondary and/or post-secondary education age group (ages 16-25), strongly preferred
• Ability to cultivate trust and build/manage strong, authentic external partnerships and relationships with a variety of people in order to maximize outcomes
• Demonstrated experience in meeting and exceeding ambitious targets
• Exceptional organizational skills and detail orientation
• Excellent project- and time-management; ability to juggle multiple, competing tasks and deadlines
• Strong verbal and written communication skills on email, phone, and in person
• Interest in, passion for, or desire to learn about youth workforce-related topics
• Excellent skills in Google Suite and Microsoft Office
• Comfort using client relationship management (CRM) and data collection platforms such as Salesforce and project management platforms such as Monday.com; comfort using or quickly learning other administrative/operational systems
• Initiative and proactive problem-solving skills; willingness to take on unexpected tasks and responsibilities
• Desire to work in a fast-paced, forward-looking nonprofit environment and strong interest in nonprofit operations and administration
• Desire to enroll in a virtual, 7-week youth coaching certification training program unless already certified
• Industry experience in the healthcare, business operations, finance, or IT sectors is a plus
• Reliable transportation to travel to in-person activities across DC and Northern Virginia, required