About Cramer Law Group
Cramer Law Group is a boutique Chicago employment law firm representing both employees and employers across the full spectrum of workplace matters — discrimination, harassment, wrongful termination, wage and hour disputes, non-competes, FMLA, ADA accommodations, and independent contractor classification. We are a lean, high-performing team that takes pride in sophisticated legal strategy, strong client relationships, and meaningful outcomes.
HOW TO APPLY — PLEASE READ CAREFULLY
Email the following four items with the subject line "Of Counsel Application — [Your Last Name]":
• Resume
• Cover letter addressing your interest in employment law and this role specifically
• A legal writing sample you personally drafted (demand letter, brief, or memorandum)
• Written responses to the three screening questions at the bottom of this posting
Incomplete applications will not be reviewed. We use this process to evaluate attention to detail and written communication — both essential to this role.
About the Role
We are seeking an experienced Of Counsel Attorney to join our team on a part-time contract basis. This is not a document-review role. From day one, you will work directly with firm leadership on substantive matters, develop real client relationships, and have the autonomy to manage your own docket. You'll gain experience on both sides of the employment relationship — a perspective few attorneys ever develop.
Core Responsibilities
• Lead pre-litigation and litigation settlement negotiations for both employee and employer clients, from demand through resolution.
• Draft demand letters, position statements, motions, briefs, and other legal documents with precision and persuasive force.
• Handle written communications with clients, opposing counsel, and administrative agencies.
• Conduct initial consultations with prospective clients — assess case viability, identify legal theories, spot conflicts, and make sound intake decisions.
• Serve as a primary point of contact for clients throughout their matters and manage professional relationships with opposing counsel, administrative agencies, and third parties.
• Collaborate with firm leadership to develop case strategy, assess risk, and achieve the best outcomes for clients.
Qualifications
• J.D. from an accredited law school and active Illinois bar admission (or eligibility for admission).
• 5–8 years of legal practice experience, with meaningful exposure to employment law — whether plaintiff-side, defense-side, in-house, or through a related practice (commercial litigation, labor relations, civil rights, administrative agency work).
• Working knowledge of federal and/or Illinois employment law (Title VII, FMLA, ADA, ADEA, FLSA, IHRA, IWPCA, or equivalents). Comprehensive expertise across all of these is not required — we will train on firm-specific procedures and substantive gaps.
• Exceptional legal writing skills — briefs, letters, and memos that are clear, concise, and compelling.
• Strong strategic instincts — ability to analyze a situation quickly and think several moves ahead.
• Professional maturity to handle sensitive client situations and adversarial communications with poise.
• Self-starter mentality suited to a boutique environment — ability to manage your own docket and deadlines.
Bonus (not required)
• Direct plaintiff-side employment experience.
• Experience with the EEOC and IDHR charge process and position statements.
• Experience drafting demand letters and conducting pre-litigation negotiations.
• Familiarity with Illinois-specific statutes (IHRA, IWPCA, IFTWA, PLAWA, Workplace Transparency Act).
• Both-sides experience (representing both employees and employers).
Preferred Skills
Legal strategy, legal writing, negotiation, litigation, contract and document review, administrative agency practice, wrongful termination, labor and employment law.
Work Authorization
Applicants must be legally authorized to work in the United States and maintain U.S. residency at the time of application.
Screening Questions (please include written responses with your application)
• Describe a negotiation where you didn't get what you initially wanted. What was your strategy, and how did it end?
• How would you handle an intake call with a prospective client who has a sympathetic story but a weak legal case?
• Describe a matter (or a significant piece of one) you managed largely on your own. What decisions did you have to make, and how did you make them?
Equal Opportunity
Cramer Law Group is an equal opportunity employer. We are committed to a diverse and inclusive workplace and do not discriminate on the basis of race, color, religion, national origin, sex, sexual orientation, gender identity, age, disability, veteran status, or any other characteristic protected by law.
Pay: $85.00 - $120.00 per hour
Application Question(s):
• Walk us through a negotiation where you didn't get what you initially wanted. What was your strategy, and how did it end?
• You're doing an intake call with a prospective client who has a sympathetic story but a weak legal case. How do you handle that conversation?
• Tell us about a time you managed a matter (or a significant piece of one) largely on your own. What decisions did you have to make, and how did you make them?
Work Location: Remote