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This position has closed. HUB International removed this listing from their careers page on Oct 5, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Insurance Due Diligence Advisor, Private Equity and M&A

HUB International · Chicago, IL · $125,000–$175,000 a year · Full time

Posted Aug 7, 2026 · We last checked this listing on Oct 4, 2026

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 insurance findings in a way a deal team will act on?

What they are checking: Whether they can turn technical findings into clear business points for buyers.

Tell me about a finding you made that changed a deal's price or terms.

What they are checking: Whether their work has had real impact on deals.

How do you manage several deals with overlapping deadlines?

What they are checking: Whether they can prioritize and deliver quality work during busy deal periods.

What would you do

A private equity firm is buying a manufacturing company and needs insurance diligence in three weeks. How do you approach it?

What they are checking: Whether they can plan a focused review under deal timelines and find what matters most.

How do you work with a target company's management when they are not eager to share information?

What they are checking: Whether they can get what they need diplomatically during a sensitive process.

How would you help a PE firm manage insurance across its portfolio companies after closing?

What they are checking: Whether they see diligence as the start of a long client relationship.

About the work

What are the most common insurance problems you find in a target company's program?

What they are checking: Whether they know where risk hides, such as gaps, low limits, old claims and poor structures.

How do you handle claims-made policies and tail coverage when a company changes ownership?

What they are checking: Whether they understand change-in-control provisions and how to protect past acts after closing.

What role does representations and warranties insurance play in a deal, and how have you worked with it?

What they are checking: Whether they understand R&W insurance and how it fits with other diligence work.

How do you estimate the cost of a target's insurance program after closing?

What they are checking: Whether they can project post-close costs that buyers need for their financial models.

Practice this interview out loud.

Offer builds a real interview for this exact role at HUB International from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by HUB International.

ABOUT US At HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is one of the largest global insurance and employee benefits broker , providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions. About The Role: HUB International's Private Equity and M&A practice serves as a trusted advisor to private equity firms, family offices, and strategic acquirers actively engaged in the M&A market. We partner with clients at every stage of the deal cycle, from initial diligence through post-close management and eventual exit, helping them understand and manage the insurance implications of their acquisitions. This role sits at the center of our pre-close advisory work. As an Insurance Due Diligence Advisor , you will serve as the primary point of contact and process lead on engagements, managing the full due diligence process from kickoff through final report. You will coordinate directly with PE deal teams, strategic acquirers, and target company executives while drawing on HUB's national network of specialty coverage experts to deliver a comprehensive picture of the target's insurance program. No two deals look alike. You will guide clients through findings spanning businesses in manufacturing, healthcare, telecommunications, specialty finance, and more, translating complex risk into clear, actionable guidance under real transaction timelines. This is a role for a highly organized, commercially minded professional who thrives in a fast-paced environment, communicates confidently with senior stakeholders, and knows how to lead a process by bringing the right experts to the table at the right time. Responsibilities: • Manage commercial insurance due diligence engagements from kickoff through final written report, running multiple projects simultaneously across different industries and transaction structures • Analyze P&C insurance programs for coverage adequacy, uncovered exposures, and pricing benchmarks relative to industry peers • Prepare and present written due diligence reports for PE clients, corporate acquirers, and deal advisors • Coordinate with HUB specialty and industry experts to address complex or niche coverage areas • Collaborate with HUB's Employee Benefits due diligence team on shared engagements, ensuring clients receive a unified and complete picture across all diligence workstreams. • Communicate directly with target company management and C-suite executives to collect and clarify diligence information • Review and interpret financial statements and risk management programs of target companies • Support ongoing client relationship management with PE firms and repeat acquirer clients Requirements: • Strong analytical and written communication skills with the ability to translate technical insurance concepts for deal teams and executives who are not insurance professionals. • 3 or more years of commercial P&C insurance experience with working knowledge of property, casualty, and specialty lines. • Highly organized with the ability to manage multiple concurrent engagements under competing deadlines without losing attention to detail. • A resourceful, self-directed professional who takes ownership of engagements and drives them forward without waiting to be told the next step. • Prior M&A or transaction-related insurance experience is a plus. • Direct experience working with or alongside private equity firms, investment banks, or deal advisors is an advantage. • Adaptable to a deal-driven, irregular workflow. • Comfortable adopting new technology and AI tools to work more efficiently and deliver better outcomes. • Bachelor's degree required. JOIN OUR TEAM Do you believe in the power of innovation, collaboration, and transformation?  Do you thrive in a supportive and client focused work environment?  Are you looking for an opportunity to help build and drive change in a rapidly growing and evolving organization?  When you join HUB International , you will be part of a community of learners and doers focused on our Core Values: entrepreneurship , teamwork, integrity, accountability, and service. Disclosure required under applicable law in California, Colorado, Illinois, Maryland, Minnesota, New York, New Jersey, Ohio, and Washington states: The expected salary range for this position is $ 125,000 - $ 175,000 and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. HUB International is proud to offer comprehensive benefit and total compensation packages: health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits such as vacation, sick, and personal days, and eligible bonuses, equity and commissions for some positions. Department Account Management & Service Required Experience: 5-7 years of relevant experience Required Travel: Negligible Required Education: Bachelor's degree (4-year degree) HUB International Limited is an equal opportunity employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations. E-Verify Program We endeavor to make this website accessible to any and all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please contact the recruiting team HUBRecruiting@hubinternational.com . This contact information is for accommodation requests only; do not use this contact information to inquire about the status of applications.