Jobs › First American

Sr. Commercial Underwriting Counsel - Hybrid Preferred/Remote USA Considered

First American · Chicago, IL · $129,300–$172,300 a year · Full time

Posted Sep 17, 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

Tell me about a time you said no to a customer request but kept the relationship strong.

What they are checking: Balancing firm risk judgment with the customer service that commercial deals require.

How do you mentor title officers or junior underwriters on difficult risk questions?

What they are checking: Leadership as a senior counsel who raises the judgment of the broader team.

How do you stay current on case law and regulatory changes that affect title insurance?

What they are checking: Commitment to ongoing legal learning in a field shaped by court decisions.

Explain a complicated title risk to a business person who just wants to close the deal.

What they are checking: Clear communication that turns legal analysis into a practical decision for customers.

What would you do

A closing is tomorrow and a mechanic's lien shows up on title. What are your options?

What they are checking: Practical problem solving under deadline, including indemnities, bonding and affirmative coverage.

How do you work with sales and escrow teams who want to win business that you think is too risky?

What they are checking: Collaborating with revenue-driven partners while holding sound underwriting standards.

About the work

A lender wants coverage over a known survey encroachment on a multi-state portfolio deal. How do you decide whether and how to insure it?

What they are checking: Risk analysis and creative underwriting that finds solutions while protecting the company.

Walk me through the endorsements you see most often in commercial deals and the risks they shift.

What they are checking: Deep command of commercial title products and what each endorsement actually exposes the insurer to.

How do you handle a deal with properties in several states with different title practices?

What they are checking: Multi-state knowledge and coordination, which National Commercial Services handles regularly.

How do you evaluate a request for creditors' rights or bankruptcy-related coverage?

What they are checking: Familiarity with high-risk coverage areas and the analysis needed before agreeing to them.

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The full job description

As published by First American.

Who We Are Join a team that puts its People First! As a member of First American's family of companies, National Commercial Services provides single-point service for simple to multi-property/multi-state national commercial real estate transactions. Since 1889, First American (NYSE: FAF) has held an unwavering belief in its people. They are passionate about what they do, and we are equally passionate about fostering an environment where all feel welcome, supported, and empowered to be innovative and reach their full potential. Our inclusive, people-first culture has earned our company numerous accolades, including being named to the Fortune 100 Best Companies to Work For® list for eleven consecutive years. We have also earned awards as a best place to work for women, diversity and LGBTQ+ employees, and have been included on more than 50 regional best places to work lists. First American will always strive to be a great place to work, for all. For more information, please visit www.careers.firstam.com. What We Do Enable you to apply your passion for law and risk analysis to real estate transactions. If you excel in collaborating with others to assess possibilities and discover solutions, it may be time to combine your analytical rigor with a premier brand in the commercial real estate space. First American is looking to add a Sr. Commercial Underwriting Counsel to our growing team. This position plays a key role in transforming commercial real estate experience by empowering our employees and customers to deliver next-generation solutions and results. What You’ll Do: • Provide underwriting support, counsel, and authorization to company personnel and customers related to the issuance of real estate title insurance commitments and policies • Utilize underwriting standards and guidelines within delegated authority limits, to underwrite the issuance of title insurance • Provide guidance to company personnel in the performance of real estate settlement services • Issue underwriting standards and guidelines in accordance with established company processes What You’ll Bring: • 8-10 years title underwriting experience, commercial experience preferred • Law Degree required and admitted to practice law in state of employment • Licensed to practice law, in good standing • Must be familiar with real estate law • Strong understanding of fundamental concepts, practices and procedures of real estate title and settlement process • Strong analytical rigor and business acumen • Strong negotiation skills and ability to provide alternative solutions or convey unpopular information with tact. • Ability to collaborate and act decisively; build relationships internally and externally • Excellent listening, verbal, and written communication skills • Strong organizational skills with the ability to multi-task, prioritize and timely follow up • Abstract thinking and creative solutions Pay Range: $129,300.00 - $172,300.00 Annually This hiring range is a reasonable estimate of the base pay range for this position at the time of posting. Pay is based on a number of factors which may include job-related knowledge, skills, experience, business requirements and geographic location. What We Offer By choice, we don’t simply accept individuality – we embrace it, we support it, and we thrive on it! Our People First culture is inclusive for all employees - not just because it's the right thing to do, but because it's the key to our success. We are proud to foster an authentic and inclusive workplace For All. You are free and encouraged to bring your entire, unique self to work. First American is an equal opportunity employer in every sense of the term. Based on eligibility, First American offers a comprehensive benefits package including medical, dental, vision, 401k, PTO/paid sick leave and other great benefits like an employee stock purchase plan.

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