College Specialist (Contractual)

Who We Serve

Since our founding in 1966, LINK has been driven by a mission to confront and close the racial gaps in education and access to opportunity for Black students. That commitment remains at the heart of our mission. Today, our Scholar community continues to reflect this legacy, with the vast majority of students identifying as Black while others identify with more than one racial background, including Latino/a, White, Asian, and Other.

We are proud that our Scholars represent the rich diversity of Chicago. We intentionally recruit students from across Chicagoland, with focused outreach in 10 neighborhoods on the south and west sides of Chicago, communities that have long experienced persistent disparities in education, economic opportunity, public safety, and health outcomes. Currently, our Scholars come from communities that represent more than 60 zip codes across Chicagoland and attend a diverse range of schools spanning Chicago, Cook County, and Lake County.

Our culturally responsive programming, rooted in academic, social-emotional, and leadership development, remains specifically designed to meet the needs of the communities we serve, honoring the multifaceted identities of our Scholars while maintaining our commitment to uplifting and empowering them to thrive in school, lead in their communities, and succeed to, through, and beyond college.

Our Scholars represent more than 60 Chicagoland neighborhoods, with a focus on supporting ten South and West Side communities: Auburn Gresham, Austin, Bronzeville, Englewood, Garfield Park, Greater Grand Crossing, North Lawndale, Roseland, South Shore, and Washington Park.

Looking to make a difference by linking students to opportunities so they can take a new path—one that leads to their full potential and our city’s vibrant future? Then join our team!

Position Summary

The College Specialist plays a critical role in supporting the college access programming for our Scholars. The College Specialist is a college access expert who will support and guide a caseload of 10-15 seniors through the college application and admissions journey. College Specialists will support our Project College curriculum, meeting with each Scholar in their caseload monthly to discuss college and scholarship applications, advise on college selection based on LINK programmatic criteria and offer college counseling services based on Scholar academic profile, interests, family preferences and other fit factors. College Specialists will work closely with the VP, Programs and Evaluation to ensure our Scholars apply and are selected to selective or highly selective colleges and universities setting them up to graduate from college with the least amount of debt.

Caseload Management

• Execute the LINK Project College Curriculum.
• Meet with Scholars on caseload monthly for one-hour sessions from September through June to discuss monthly topics and provide college counseling services such as insight on next steps, share resources as necessary, FAFSA support, follow-up on communicated next steps, assess progress, etc. Note: select sessions include Mentors and/or Parents.
• Submit case notes and progress accurately and on time in Salesforce and/or other trackers.
• Collect and document data related to the outcomes of Scholars’ college applications (e.g. college applications, financial aid & scholarship award letters, etc.).
• Create college decision reports/suggestions for each Scholar on caseload.
• Lead parent/Scholar/Mentor outreach (including post-session homework communications), initial engagement interventions, and decision meetings for caseload.
• Identify Scholars who require additional interventions and work with the LINK liaison to support them.
• Ensure the dissemination and collection of all Scholar feedback surveys after each counseling session.
• Complete all requested feedback forms and surveys.

Training/Development

• Attend mandatory 3-hour College Specialist in-person orientation on Wednesday, September 17th at 5:30p at the LINK office.
• Attend mandatory 90-minute virtual training and development sessions each month to align on approach, address challenges, and ensure equitable service delivery.
• Attend mandatory in-person meet and greet with senior Scholars on October 25th, 2025, from 2:30p-3:30p.

Scholar Workshop Planning & Facilitation

• Collaborate with LINK staff to determine workshop content and format that align with Scholar needs and LINK’s college access curriculum.
• Support creation of workshop materials, including presentations, handouts, and reflection activities.
• Facilitate or co-facilitate sessions with LINK staff or other College Specialists in a way that promotes inclusivity, engagement, and active learning on select Saturdays.
• Participate in three virtual planning meetings in advance of each workshop.
• Debrief with LINK staff after each session to share feedback and reflect on improvements for future workshops

Qualifications

• Bachelor’s degree REQUIRED.
• Minimum of two (2) years of relevant work experience in direct college counseling.
• Strong experience in college counseling, with a particular focus on guiding students through the decision process at competitive institutions.
• Experience working with low-income, first-generation, and/or underrepresented Chicago youth and their families.
• Knowledge and awareness of financial aid supports including navigating the FAFSA, competitive scholarships, and national and local scholarships.
• Ability to remain flexible and adapt to changing needs and priorities.
• Must live in the Chicagoland area.

Characteristics

• Exemplifies the LINK Unlimited Scholars’ mission, vision, and values and acts in accordance with all policies and procedures of the organization.
• Demonstrates a growth mindset and servant leader approach to educating underrepresented youth in Chicago.
• Must have an outgoing and engaging personality and a cheerful and welcoming demeanor.
• Must have a strong work ethic and be a self-starter.
• Must be a creative and forward thinker.
• Must have the utmost integrity and an ability to process, protect and exercise discretion in handling confidential information and materials.
• Exercises good judgment with an ability to manage situations with tact and discretion.

Work Schedule

Part-time during the evenings and weekends - Specialists will utilize a scheduling platform to set up appointments with their caseloads monthly. The term for this role is September 2025 - June 2026.

Compensation

Specialists will be compensated based on sessions held with Scholars and can anticipate working 1.5 hours per Scholar per month (totaling 15 hours for a caseload of 10 Scholars). The hourly rate is $27/hour and Specialists may earn up to $4,455 over the course of the year.

This is a 1099 independent contractor role. Compensation will be paid monthly upon timely submission of deliverables.

To Apply

Submit your resume and cover letter to Alexandria Cummings, VP, Programs & Evaluation

LINK Unlimited Scholars is an equal opportunity employer.