Assistant Counsel Jobs in Chicago, IL
Assistant Counsel jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Magnificent Mile corridor, across corporate legal departments, financial services, insurance, and healthcare. Employers hiring right now include City of Chicago, IL, Avant, and CoreSite. See the openings below and apply to the ones that match your experience.
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Job Title
Assistant General Counsel - Canada/US
Job Description Summary
Job Description
Position Summary
This role provides strategic legal counsel to an assigned region and/or line of business within a matrixed legal department. The lawyer operates as an embedded advisor — building deep fluency in the business's personnel, operations, deal flow, and risk profile — rather than as a transactional resource. The role is deliberately scoped to keep the lawyer focused on judgment-intensive, business-critical work, with routine and specialist functions carried out by centralized teams (as detailed below).
Reporting & Matrix Structure
Reports on a solid line to the Associate General Counsel for the Americas region, with alignment to the business unit(s) supported. Coordinates regularly with centralized Centers of Excellence and/or Functions: Contracts COE, Litigation & Risk, M&A/Corporate, Legal Operations, Ethics & Compliance, and EHS.
Core Responsibilities — In Scope
Strategic Business Partnering
- Serve as the primary legal point of contact for an assigned region/business, maintaining working knowledge of its organizational structure, key personnel, revenue drivers, and operating risks.
- Attend business leadership meetings as a standing advisor to spot legal issues early and shape decisions before they become problems.
- Translate business strategy and objectives into legal risk assessments and practical, actionable recommendations.
- Build trusted relationships with business leaders so legal is consulted proactively, not after the fact.
Complex & Business-Critical Contract Guidance
- Serve as an escalation point and advisor to the centralized commercial contracts team on agreements that are non-routine, high-value, precedent-setting, or carry elevated risk.
- Review and advise on deal structure, unusual terms, indemnification/liability positions, and regulatory considerations for business-critical agreements.
- Determine, in consultation with the centralized contracts team, when an agreement should be escalated from routine handling to direct counsel involvement.
- Do not perform first-line drafting, redlining, or negotiation of routine commercial contracts — that work stays with the centralized contracts COE.
Risk Identification, Escalation & Governance
- Identify legal and regulatory risk within the assigned business and escalate to the appropriate centralized group (Litigation & Risk, Ethics & Compliance, EHS) with context and recommended action.
- Advise business leaders on the practical application of company policy, delegation of authority, and approval protocols.
- Support internal audits, investigations, and compliance reviews touching the assigned business by supplying business context and coordinating with the business.
Supporting Role in Litigation
- Act as the business liaison for litigation matters affecting the assigned region/business: gathering facts, coordinating witnesses, and managing document/data collection requests.
- Provide business and operational context to the centralized Litigation & Risk team and outside counsel; flag new claims or disputes as they arise.
- Do not manage case strategy, retain or direct outside counsel, or own litigation budgets — that responsibility sits with the centralized Litigation & Risk team.
Supporting Role in M&A
- Provide business intelligence, personnel context, and operational due diligence support to the centralized M&A/Corporate team on transactions involving the assigned region/business.
- Flag region or business-specific risks (contracts, regulatory, personnel) relevant to a deal early in the process.
- Do not lead deal structuring, negotiate transaction documents, or own the M&A workstream — that responsibility sits with the centralized M&A team.
Training, Communication & Process
- Deliver periodic legal training and policy updates tailored to the assigned business's operations and risk areas.
- Maintain awareness of jurisdiction-specific legal and regulatory developments relevant to the assigned region.
- Contribute to the continuous improvement of legal playbooks, escalation triggers, and matrixed working protocols.
Explicitly Out of Scope
These functions are intentionally excluded from this role and are owned by other teams. Regional/business counsel should redirect these matters rather than take them on directly:
Excluded Function [Owned By]
Routine commercial contract review, negotiation, and drafting [Centralized Contracts team]
Legal entity management (incorporations, filings, corporate secretarial) [Outsourced entity management vendor]
Litigation management: strategy, outside counsel direction, budgets [Centralized Litigation & Risk team / outside counsel]
M&A deal leadership and transaction document negotiation [Centralized M&A / Corporate team]
Required Qualifications
- J.D. and active bar admission in the US; 10+ years' combined law firm and/or in-house experience; licensed to practice law in Ontario or another Canadian province, a plus.
- Demonstrated ability to operate effectively in a matrixed organization, balancing regional and business-line stakeholders.
- Sound commercial judgment and the ability to distinguish routine issues from business-critical ones requiring direct counsel involvement.
- Strong stakeholder management and communication skills; comfortable advising senior business leaders.
- Experience in commercial real estate, professional services, or a similarly complex multinational operating environment is preferred.
- Fluency in French, a plus.
How Success Is Measured
Business leaders proactively consult legal on emerging issues rather than after the fact. Escalations to centralized teams (Litigation, M&A, Compliance) are timely, well-framed, and appropriately scoped. Legal risk within the assigned business is identified and mitigated before it materializes into loss, claim, or regulatory exposure. Routine work stays with the centralized teams designed to handle it, preserving this role's capacity for judgment-intensive matters.
Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and unpaid time away from work. In addition to a comprehensive benefits package, Cushman and Wakefield provide eligible employees with competitive pay, which may vary depending on eligibility factors such as geographic location, date of hire, total hours worked, job type, business line, and applicability of collective bargaining agreements.
The compensation that will be offered to the successful candidate will depend on factors such as whether the position is covered by a collective bargaining agreement, the geographic area in which the work will be performed, market pay rates in that area, and the candidate’s experience and qualifications.
The company will not pay less than minimum wage for this role.
The compensation for the position is: $ 187,000.00 - $220,000.00 Cushman & Wakefield is an Equal Opportunity employer to all protected groups, including protected veterans and individuals with disabilities. Discrimination of any type will not be tolerated.
In compliance with the Americans with Disabilities Act Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position at Cushman & Wakefield, please call the ADA line at 1-888-365-5406 or email Accommodations@cushwake.com. Please refer to the job title and job location when you contact us.
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Who's Hiring



Top Industries Hiring
- Education
Assistant Counsel Jobs in Chicago: Frequently Asked Questions
How do I get a assistant counsel job in Chicago?
Focus your search on Chicago's Loop and River North, where corporate legal teams, insurance carriers, and financial institutions cluster most heavily. Candidates with transactional experience in commercial contracts, regulatory compliance, or healthcare law have the clearest edge in this market. Building relationships through the Chicago Bar Association and targeting in-house legal departments at midsize firms headquartered downtown will open more doors than broad applications.
Which companies hire assistant counsels in Chicago?
Companies currently hiring assistant counsels in Chicago include City of Chicago, IL, Avant, and CoreSite, per current listings on Migrate Mate as of November 2026. Chicago's mix of Fortune 500 headquarters, major insurers, and large regional healthcare systems makes it one of the strongest in-house legal markets in the Midwest.
Are there remote assistant counsel jobs in Chicago?
Yes, though remote availability depends on the role. Contract review, compliance advisory, and research-heavy positions tend to be the most remote-friendly, while litigation support and roles requiring in-person client or court interaction are typically on-site. About 100% of assistant counsel openings tied to Chicago are remote or hybrid as of November 2026, with hybrid arrangements most common among Loop-based corporate legal departments.
How can I get a assistant counsel job in Chicago with little or no experience?
The most realistic entry path in Chicago is through a legal internship or contract role with one of the city's large insurance companies, healthcare networks, or municipal agencies, which regularly bring on junior counsel for defined-scope work. Positions like legal analyst, contracts coordinator, or compliance associate at Chicago-based firms serve as strong lateral moves into a formal assistant counsel role. Volunteering with Chicago Volunteer Legal Services can also demonstrate practical experience that in-house teams value.
Which industries hire the most assistant counsels in Chicago?
The sectors hiring the most assistant counsels in Chicago are Education, based on current listings on Migrate Mate as of November 2026. Chicago's concentration of major insurance carriers, regional banks, and large healthcare systems means steady in-house demand that outpaces most other Midwest markets.
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