Position:  Enrollment and Matching Strategist

Reporting Relationship:  Manager, Enrollment

FLSA Classification: Exempt

Work Schedule:  11:00 – 7:00 p.m. (with flexibility for later evenings/weekends)

Salary Range:  $55K - $57K Commensurate with work experience, degree credential(s) and bilingual language skillset

Benefits:  BBBS offers a competitive benefits package which includes Health and Dental coverage, Vision, Critical Illness, Accidental coverage, Voluntary and Basic Life Insurance, Short and Long-term disability, Flexible Spending Account, and a matching 401K retirement plan.   

ABOUT BIG BROTHERS BIG SISTERS OF METRO CHICAGO (BBBSChi):

BBBSChi’S Mission is to create and support one-to-one mentoring relationships that ignite the power and promise of youth.

BBBSChi’S Vision is that all youth achieve their full potential.

Big Brothers Big Sisters of Metropolitan Chicago is an affiliate of the nation’s largest donor-and volunteer-supported mentoring network. We provide high quality mentoring services to thousands of children and their families across Cook, DuPage and Lake Counties in both Illinois and Indiana. Big Brothers Big Sisters carefully matches children (“Littles”) with caring, screened and trained adult mentors (“Bigs”). Throughout the course of their mentoring relationship (“match”), we monitor and support the match, providing safety and quality measures, as well as outcome-based activity ideas and goals. Learn more at www.BBBSCHGO.org.   

BBBSChi’s Core Value is that we deeply believe Access, Belonging, and Opportunity is paramount and fundamental to BBBSChi’s success. We all work to build and maintain a positive work environment for our staff, volunteers, and program participants. It is our belief that every staff member should embrace these principles in the decision-making process. Therefore, we fully expect the ideal candidate will carry out their function with these core values in mind and treat everyone respectfully and fairly.

 Position Summary:

 The Enrollment and Matching Strategist will work closely with the Manager of Enrollment to handle all aspects of enrollment and matching to ensure that goals set for programs are met.

 Supervisory Responsibilities:

There are no supervisory responsibilities in this position, but functions as a senior-level subject matter expert and may support onboarding/training of seasonal or new staff.

Responsibilities:

 Core Responsibilities include full-cycle enrollment and matching for volunteers and youth/families across Cook, DuPage, and Lake Counties (IL) and Northwest Indiana. This includes high-volume interviewing, assessment writing, match presentation, and scheduling match introductions.

1.      Build and maintain strong professional relationships with prospective volunteers and youth/families from initial inquiry through successful match.

2.     Coordinate scheduling of all interviews in partnership with corporate, community, and school partners; conduct interviews virtually or in person as required.

3.      Conduct a minimum of 25 volunteer interviews and youth/family interviews per month, maintaining high quality and consistency.

4.     Complete 25 written assessments and recommendations within 48 hours of interview, ensuring accuracy, clarity, and professional judgment in all match decisions. This role includes the use of agency-approved AI technology to support the creation, refinement, and timely completion of written assessments.

5.     Provide weekly schedules, performance updates, and pipeline reports to the Manager of Enrollment.

6.     Support recruitment efforts by distributing materials, presenting to partner organizations, attending community events, and collaborating with school/site partners to increase enrollment as needed.

7.      Identify bottlenecks, propose solutions, and proactively strategize with the Manager of Enrollment to ensure enrollment flow and timely matching.

8.     Create safe, appropriate, and mission-aligned match relationships based on available volunteers and youth.

9.     Present match recommendations to all parties by phone and secure verbal approval from volunteers and families.

10.   Prepare match notes and schedule 5–10 match introduction meetings per week, ensuring accurate and timely handoff to the MIM Coordinator or Program/Partnership staff.

11.    Personally conduct a minimum of 3 Match Introduction Meetings per week.

12.   Meet or exceed senior-level match goals (elevated baseline expectations from standard capacity due to senior classification).

13.   Collaborate with Program staff to ensure a seamless transition from enrollment to match support.

14.   Conduct volunteer and child reassessments when needed.

15.   Maintain accurate, compliant, and up-to-date files for all volunteers and children/families.

16.   Once fully onboarded and consistently meeting performance expectations, support onboarding, training, and peer coaching for new staff.

17.   Review and approve own files as assigned by leadership.

18.   Incorporate Agency approved AI-supported tools (e.g., Microsoft Copilot) to enhance service delivery, improve workflow efficiency, and support high-quality, timely documentation while upholding confidentiality and ethical standards   

19.   Perform additional duties as assigned.

Skills and Qualifications:

·       Strong commitment to the Mission and Vision of BBBS.

·       Bachelor’s degree in social services, psychology, or related field required. Master’s degree preferred.

·       Minimum 4 years of direct experience in case management, social services, or a related field.

·       Advanced interviewing, assessment, and decision-making skills required.

·       Experience working with children, youth development, or family services.

·       Bilingual (English/Spanish) preferred.

·       Strong written and verbal communication skills, including phone and email professionalism.

·       Strong facilitation and public speaking experience.

·       High customer-service orientation with the ability to engage volunteers and families effectively.

·       Exceptional organization, time management, and ability to handle multiple priorities in a fast-paced environment.

·       Strong attention to detail and capacity for writing high-quality assessments.

·       Ability to work independently while exercising sound professional judgment.

·       Intermediate proficiency in Microsoft Office; Salesforce experience preferred.

·       Must have reliable transportation, valid driver’s license, and auto insurance; regular travel throughout Chicago and suburban counties is required.

·       Requires flexibility to work evenings and weekends. Work hours for this position are typically 11am to 7pm.

Work Environment:

This position operates in a professional office environment.

This role routinely uses standard office equipment such as computers, phones, photocopiers, etc.

There is an expectation to work in office a minimum of two days per week.

 To apply Please forward your resume, cover letter and salary requirements to:

BBBS Careers Apply Here

Big Brothers Big Sisters of Metropolitan Chicago

Attn: Human Resources

130 S. Jefferson, 2^nd Floor  

Chicago, IL 60661

BBBS is an Equal Employment Opportunity Employer