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Senior Legal Counsel - Employment, Benefits and Compensation

BMO · Chicago, IL · $120,000–$250,000 a year · Full time

Posted Sep 14, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

How do you explain a legal position to a human resources partner who needs to act on it today?

What they are checking: Whether they can give an HR partner a clear, actionable answer the same day, rather than a long legal analysis.

Tell me about advice you gave that turned out to be wrong or incomplete. What did you do?

What they are checking: Honesty at a senior level where most candidates present only wins

What would you do

Walk me through how you'd advise on a proposed termination where the facts are messy.

What they are checking: Whether they give practical, usable advice on a messy termination, rather than a memo that lists risks without recommending anything.

A business leader wants to do something you think is legally risky but not clearly prohibited. How do you handle that?

What they are checking: Whether they help the business weigh risk and find a workable path, rather than simply refusing whenever something is uncertain.

How do you decide when to bring in outside counsel and when to handle something in house?

What they are checking: Whether they weigh cost, expertise and capacity sensibly when deciding to use outside counsel, rather than escalating by habit.

What's your view on where the line sits between advising the company and advising an individual employee?

What they are checking: Whether they are clear that the company is the client, and can say so kindly when an employee assumes otherwise.

The posting is at 320 South Canal Street in Chicago with an in-office emphasis and an application deadline of September 30, 2026. Does that work for you?

What they are checking: Whether the Chicago location, in-office expectation and September 30 deadline genuinely work for them before anyone invests further time.

About the work

This role advises on United States employment, compensation and employee benefits matters in financial services. Which of those three is your deepest area?

What they are checking: Which of employment, compensation and benefits law they truly know best, since claiming equal depth in all three rarely holds.

What's your experience with retirement plan law and the federal rules governing employee benefit plans?

What they are checking: The benefits half of the role, which many employment lawyers lack

How do you advise on compensation arrangements in a regulated financial institution, where pay itself is supervised?

What they are checking: Whether they know that bank pay is supervised, including incentive compensation rules, which ordinary employment lawyers often miss.

Practice this interview out loud.

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The full job description

As published by BMO.

Application Deadline: 11/30/2026 Address: 320 S Canal Street Job Family Group: Legal At BMO, our workplace plays an important role in fostering collaboration, innovation, mentorship, and career growth. We bring teams together to solve complex challenges, share ideas, and build meaningful connections. This is a hybrid role based in Chicago, requiring a minimum of three days per week in the office at 320 S. Canal Street, with an anticipated increase to 4-5 days per week in the future. As Senior Legal Counsel, Employment, Benefits & Compensation, you will provide strategic legal and regulatory advice on a broad range of U.S. employment law, employee benefits (including ERISA), and compensation matters across BMO Financial Group. Partnering closely with business and HR leaders, you will help shape decisions, manage legal risk, and support key organizational initiatives while navigating an evolving regulatory landscape. Provides legal advice based on knowledge of legal principles, practices and procedures, and knowledge of the financial services industry and its environment. Influences and negotiates to achieve business objectives. Works to achieve organizational goals while minimizing legal risk. Additional responsibilities include: • Provides advice and counsel on wide range of employment, compensation, and employee benefit/ERISA matters, including on retirement plans, and health and welfare plans, and on issues including employee relations, performance management, leaves of absence and accommodations, wage and hour, pay equity, internal investigations, compensation and benefits, contingent workers, immigration, recruitment, inclusion, and mergers, acquisitions and outsourcing. • Makes recommendations to senior leaders on strategy and new initiatives, based on an in-depth understanding of the business/group. • May participate in the design of legal advice strategies & approaches for the unit activity and making recommendations to minimize legal issues. • Acts as the prime subject matter expert for internal/external stakeholders. • Exercises judgement on complex, confidential and sensitive matters • Identifies and resolves moderately complex issues. • Determines root causes and negotiates resolutions. • Delivers legal advice, instructs external counsel and ensures compliance with internal policies & procedures for a single or small number of function(s). • Acts as a subject matter expert on relevant laws, regulations and policies. • Resolves daily issues and/or escalates with appropriate analysis and/or recommendations. • Identifies risks and implements appropriate actions to mitigate them. • Implements continuous improvements to ensure alignment with marketplace practices and industry standards. • Builds effective relationships with internal/ external stakeholders. • Geographic scope: up to global. • Operates at a group/enterprise-wide level and serves as a specialist resource to senior leaders and stakeholders. • Applies expertise and thinks creatively to address unique or ambiguous situations and to find solutions to problems that can be complex and non-routine. • Implements changes in response to shifting trends. • Broader work or accountabilities may be assigned as needed. Qualifications: • Typically 7 years of legal practice or an equivalent combination of education and experience. • Degree in law (LLB or JD) and license to practice law in relevant jurisdiction. • Private practice, in-house experience or experience at regulatory body relating to the regulation of business/group activities may be required. • Knowledge in legal field, typically with a functional or business line specialization. • Knowledge of business and regulatory environment in which BMO Financial Group operates. • Advanced knowledge of subject matter legal requirements and the operations of a single client group. • Negotiation skills - in depth. • Seasoned professional with a combination of education, experience and industry knowledge. • Verbal & written communication skills - In-depth / Expert. • Analytical and problem-solving skills - In-depth / Expert. • Influence skills - In-depth / Expert. • Collaboration & team skills; with a focus on cross-group collaboration - In-depth / Expert. • Able to manage ambiguity. • Data driven decision making - In-depth / Expert Salary : $120,000.00 - $250,000.00 Pay Type: Salaried The above represents BMO Financial Group’s pay range and type. Salaries will vary based on factors such as location, skills, experience, education, and qualifications for the role, and may include a commission structure. Salaries for part-time roles will be pro-rated based on number of hours regularly worked. For commission roles, the salary listed above represents BMO Financial Group’s expected target for the first year in this position. BMO Financial Group’s total compensation package will vary based on the pay type of the position and may include performance-based incentives, discretionary bonuses, as well as other perks and rewards. BMO also offers health insurance, tuition reimbursement, accident and life insurance, and retirement savings plans. To view more details of our benefits, please visit: https://jobs.bmo.com/global/en/Total-Rewards About Us At BMO we are driven by a shared Purpose: Boldly Grow the Good in business and life. It calls on us to create lasting, positive change for our customers, our communities and our people. By working together, innovating and pushing boundaries, we transform lives and businesses, and power economic growth around the world. As a member of the BMO team you are valued, respected and heard, and you have more ways to grow and make an impact. We strive to help you make an impact from day one – for yourself and our customers. We’ll support you with the tools and resources you need to reach new milestones, as you help our customers reach theirs. From in-depth training and coaching, to manager support and network-building opportunities, we’ll help you gain valuable experience, and broaden your skillset. To find out more visit us at http://jobs.bmo.com/us/en BMO is proud to be an equal employment opportunity employer. We evaluate applicants without regard to race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or any other legally protected characteristics. We also consider applicants with criminal histories, consistent with applicable federal, state and local law. BMO is committed to working with and providing reasonable accommodations to individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please send an e-mail to BMOCareers.Support@bmo.com and let us know the nature of your request and your contact information. Note to Recruiters: BMO does not accept unsolicited resumes from any source other than directly from a candidate. Any unsolicited resumes sent to BMO, directly or indirectly, will be considered BMO property. BMO will not pay a fee for any placement resulting from the receipt of an unsolicited resume. A recruiting agency must first have a valid, written and fully executed agency agreement contract for service to submit resumes.

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