Paralegal

Job Title: Paralegal

Department: Legal Clinic

Reports To: Attorney/ Legal Clinic Director

Employment Status: Full\-time, Salaried, Exempt

Compensation: $47,000 annually

About Teamwork Englewood:

Teamwork Englewood is a nonprofit organization based in Chicago, dedicated to empowering residents of Englewood and surrounding neighborhoods through a variety of community\-driven initiatives. The organization offers planning and services for youth development and parent programming, workforce development assistance, and aid with re\-entry from incarceration. Teamwork Englewood’s mission is to improve the quality of life of the residents and stakeholders of Englewood by facilitating economic, educational and social opportunities. The focus of the Re\-Entry Department is on creating pathways for social equity, strengthening the community, and providing critical support to individuals seeking criminal record relief. We are committed to advancing justice, reducing recidivism, and offering second chances to people who have been impacted by the criminal justice system.

Position Summary:

The Paralegal serves as the senior point of contact for record relief cases, specializing in criminal record expungements, sealing petitions, and healthcare waivers aimed at minimizing the impact of background checks on employment and housing opportunities. This role combines advanced legal administrative support with leadership responsibilities, including training new staff and overseeing clinic operations related to post\-conviction relief. The Paralegal is also responsible for coordinating with clients, courts, attorneys, and government agencies to facilitate second\-chance legal remedies for individuals who the justice system has impacted.

Experience in criminal law is valuable as it is a commitment to the mission of TWE to bring access to justice for individuals with criminal backgrounds.

Key Responsibilities:

· Prepare, file, and track expungement and sealing petitions by state law (e.g., the Illinois Criminal Identification Act).

· Analyze rap sheets and court dockets to determine eligibility for record relief under current statutes.

· Draft legal documents including petitions, motions, affidavits, letters to court personnel, and correspondence to state’s attorneys, clerks, and judges.

· Communicate with clerks, state’s attorneys, and court officials to resolve issues and confirm hearing outcomes.

· Maintain case files and ensure compliance with court deadlines and all procedural requirements to facilitate petition success.

· Conduct background check reviews using the clerk's county websites or state websites repositories to verify sealing eligibility.

· Assist clients in completing Healthcare Worker Registry Waiver Applications to waive disqualifying background flagged offenses.

· Collect supporting documentation (e.g., rehabilitation letters, certificates, court disposition, character references, drug test results).

· Assist clients in drafting narratives that explain rehabilitation, mitigate circumstances, and justify waiver approval.

· Conduct intake interviews to assess client eligibility for record relief or healthcare waivers.

· Explain legal rights and procedures clearly to clients with little to no legal knowledge.

· Coordinate clinic events, expungement summits, and legal workshops with community partners and attorneys.

· Supervise and mentor junior paralegals, interns, and law student volunteers.

· Conduct onboarding and train new staff on expungement law, healthcare waivers, record analysis, data entry protocols, and case tracking procedures.

· Ensure compliance with data security, privacy protocols, and document retention policies.

· Develop workflows, checklists, and training materials to ensure consistency and quality control.

· Maintain and update legal clinic databases and case tracking systems (e.g., LegalServer, Clio).

· Organize and file court documents, client waivers, and correspondence.

· Schedule client appointments, follow\-ups, and court hearings as needed.

· Generate monthly reports on clinic performance, number of petitions filed, success rates, and pending cases.

· Organize legal clinics and expungement summits in partnership with attorneys and community organizations.

Additional responsibilities:

· Maintaining accurate and organized files in databases in reference to the Legal Clinic.

· Completing substantive intakes with potential clients vetting rap\-sheets for compliance.

· Conducting fact investigation and research in reference to file integrity.

· Managing electronic case filings and docketing court dates and deadlines as they come in.

· Maintaining records for grant compliance and reporting.

· Supporting attorney/s with case management and document preparation when needed.

· Maintaining ongoing and effective communication and a positive rapport with clients.

· Collaborating with partners and court staff where needed to support clients with their cases.

· Answering general phone calls and emails from clients and partners.

· Assist in preparation of petitions, waivers, and certifications.

· Conduct educational presentations at community locations and organizations and revise and develop presentations as needed under the guidance of the supervisor.

· Attends all staff and assigned meetings while demonstrating an understanding of TWE policies and procedures.

Skills \& Tools:

· Criminal Record Relief (Expungement, Sealing)

· Healthcare Background Waivers (IDPH Compliance)

· Case Management Systems (Google/Excel/Salesforce)

· Court Filing Systems (Monarch/ in\-person filing, Document Tracking)

· Client Advocacy \& Public Speaking

Qualifications:

· High School Diploma or GED and 1 – 3 years of paralegal experience; Paralegal Certificate or Associate/Bachelor’s degree in Legal Studies, Criminal Justice, or related field. Successful completion or enrolled in a peer educator training preferred.

· 1 – 3 years of paralegal experience preferred with some experience in criminal background.

· Highly organized with demonstrated success in providing legal support and maintaining and processing client records.

· Experience in office administration and case management preferred.

· Detail\-oriented with demonstrated commitment in excellence.

· Able to manage multiple projects and work well both independently or with team, in office or in remote setting.

· Strong understanding of racial and economic justice, how race and power shape systems in our society, and how grassroots organizing works in practice.

· A non\-judgmental, empathetic, caring individual with the ability to listen well and to demonstrate confidentiality and respect for clients regardless of all ethnic, religious, and socio\-economic groups.

· Must be open\-minded, flexible, responsible, engaging, and self\-motivated. Needs to be comfortable talking with formerly incarcerated individuals regardless of the offense/s.

· Experience supervising or training staff in a legal setting is preferred.

· Proficiency with legal case management software and e\-filing platforms.

· Proficiency in Microsoft office and Google Suite.

· Excellent written communication, client service, and organizational skills.

· Ability to work flexible hours, including evenings and weekends.

· Bilingual Preferred

Core Competencies and Personal Attributes:

· Commitment to racial and social justice and community empowerment

· Empathy, patience, and discretion

· Collaborative team player with strong ethics

· Proficiency in legal research and writing

· Comfortable using legal case management systems (Salesforce) is desired

· Experience with Microsoft Office/Google Suite

Compensation:

The annual salary is $42,000 \- $48,000, grant funded and subject to changes at any time.

Teamwork Englewood also offers a comprehensive benefits package, including health insurance (medical, dental, and vision), paid time off, and professional development opportunities.

Work Location \& Schedule:

This is a full\-time, in\-person position based at Teamwork Englewood’s office in Chicago’s Englewood neighborhood. The role follows a standard Monday\-to\-Friday schedule, 9 a.m. – 5 p.m. with some evening and weekends. Flexibility is needed for outreach and other community events.

How to Apply:

Interested candidates should submit a resume, cover letter, and 2\-3 references to employment@teamworkenglewood.org

In your cover letter, please address your interest in the position, previous work experience, commitment to criminal justice reform, and any other relevant information.

Job Type: Full\-time

Pay: $42,000\.00 \- $48,000\.00 per year

Benefits:

• Dental insurance
• Flexible schedule
• Flexible spending account
• Health insurance
• Paid sick time
• Paid time off
• Professional development assistance
• Vision insurance

Application Question(s):

• Do you have a HS diploma/GED AND 1\- 3 years of paralegal experience?
• Do you have a Paralegal Certificate and/or Associate/Bachelor’s degree in Legal Studies, Criminal Justice, or related field?
• Do you have at least 1 year of direct work experience with any of the following:
• Criminal Record Relief (Expungement, Sealing)
• Healthcare Background Waivers (IDPH Compliance)
• Case Management Systems (Google/Excel/Salesforce)
• Court Filing Systems (Monarch/ in\-person filing, Document Tracking)
• Client Advocacy \& Public Speaking

If so, which one(s)?

Ability to Commute:

• Chicago, IL 60621 (Required)

Ability to Relocate:

• Chicago, IL 60621: Relocate before starting work (Required)

Work Location: In person