Chicago, IL
Senior Legal Counsel jobs in Chicago, IL
4 open roles from 3 employers. Checked Oct 6, 2026.
What these openings look like
3 employers are hiring here: Wolters Kluwer, Jones Lang LaSalle and Northern Trust. 3 of the 4 publish a pay range, running $128,900 to $272,300 a year. The rest do not say. Every posting is full time. The most recent went up on Oct 2, 2026.
Every listing links to the employer's own application. Nothing is posted here on their behalf, and nothing is reposted from anywhere else.
Open roles
What it pays here
Only some employers publish a range. These are the ones that did, as written in their own postings:
- $128,900–$226,050 a year
- $160,100–$272,300 a year
What they ask senior legal counsel candidates here
Drawn from the 4 open postings on this page. The ones that come up across several employers are near the top.
Walk me through how you'd structure a SaaS customer agreement for a clinical decision support product like UpToDate.
What they are checking: Whether they understand licensing, liability, data use and service terms specific to clinical software and content.
A large health system wants unlimited liability for errors in drug information. How do you respond?
What they are checking: Whether they can protect the company from outsized risk while keeping the deal alive with a reasonable compromise.
What regulatory issues would you watch for with medication decision support tools like Medi-Span?
What they are checking: Whether they know where FDA device rules, HIPAA and clinical content claims can create risk for these products.
Tell me about a negotiation where you had to give something up to close. How did you decide what?
What they are checking: Whether they negotiate with business judgment and know which terms really matter.
How do you give advice to a business leader who wants a quick yes on something risky?
What they are checking: Whether they can explain risk clearly and offer options, rather than just saying no or giving in.
How would you handle a customer agreement for a hospital outside the United States?
What they are checking: Whether they can spot data transfer, local law and language issues, since the role supports international segments.
Tell me about a time you managed a litigation or dispute matter alongside your transactional work.
What they are checking: Whether they can handle the range of matters the role covers, from contracts to litigation support.
How do you keep up with a high volume of contracts without losing quality?
What they are checking: Whether they use templates, playbooks and prioritization to serve the business at speed.
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