[Skip to main content](#main-content) [OpenNash Jobs](https://jobs.opennash.com/) [Hiring report](/reports/hiring/) · [All Fairfax Financial jobs](https://jobs.opennash.com/companies/fairfax-financial/) · [Search jobs](/search/) Fairfax Financial · Chicago, IL # Senior Facultative Underwriter Chicago, IL, US Senior individual contributor $135,000 to $175,000 Listed on Fairfax Financial’s official careers site. Posted September 29, 2026. Check that it is still open and apply there. [Apply on Fairfax Financial’s careers site →](https://careers.odysseygroup.com/job/New-York-Senior-Facultative-Underwriter-NY-10001/1424813700/) [OpenNash Jobs](https://jobs.opennash.com/) / [Fairfax Financial](https://jobs.opennash.com/companies/fairfax-financial/) / Senior Facultative Underwriter ## Job description Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London. OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth. OdysseyRe is rated A+ (Superior) by AM Best and AA- (Very Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH. Senior Facultative Underwriter We’re seeking a passionate and experienced Senior Facultative Underwriter to oversee and manage a diverse portfolio of general casualty lines of business. This is an exciting opportunity for an individual who thrives in a fast-paced, client-focused environment and is eager to take on leadership responsibilities in a collaborative, forward-thinking company. ### Key Responsibilities Strategic Underwriting: Lead comprehensive underwriting analysis for both existing and prospective clients by evaluating experience, exposure, management quality, financial stability, and competitive positioning to assess the profitability of reinsurance transactions. ### Client Relationship Management Foster and nurture strong relationships with key clients and intermediaries, working closely with senior management to ensure the highest levels of service and satisfaction. ### Cross-Functional Leadership Oversee and coordinate efforts across claims, actuarial, and accounting teams to ensure seamless execution of business initiatives and risk management processes. ### Marketing & Business Development Represent Odyssey Re to reinsurance intermediaries, clients, and prospects through active engagement in industry events, seminars, conferences, and direct marketing activities. ### Strategic Planning Play an integral role in the company’s planning process, contributing to both department-specific and organization-wide goals and strategies. ### Mentorship & Leadership Provide guidance and support to Associate Underwriters, instilling the company's mission, culture, and performance goals while driving technical underwriting excellence and profitability. ### Experience Needed: Industry Expertise: Base understanding of reinsurance and insurance principles, including coverage structures, pricing techniques, distribution channels, and organizational dynamics. ### Exceptional Communication Strong verbal and written communication skills to engage clients, colleagues, and stakeholders effectively. ### Analytical & Interpersonal Skills Ability to analyze complex data while building meaningful relationships with both clients and internal teams. ### Leadership Capabilities Experience in managing support staff and client relations with discretion and independent judgment. ### Travel-Ready A willingness to travel for client meetings, industry events, and business development activities. ### Tech Savvy Proficiency in MS Word, Excel, PowerPoint, and Outlook. ### Education A Bachelor’s degree in a relevant field. Relevant years of experience in underwriting complex casualty and casualty accounts, with a proven track record in managing large portfolios and driving profitable outcomes. Why Odyssey Re? At Odyssey Re, we foster a culture of innovation, collaboration, and growth. You’ll be part of a supportive team that values your expertise and offers ample opportunities to advance your career. Join us and play a key role in shaping the future of reinsurance! ### Disclaimer In New York City, NY, the base salary for this position ranges from $135,000 to $175,000. Additionally, the role may be eligible for a discretionary annual incentive program. The final offer will be determined based on the candidate’s skills and experience, along with other relevant factors. Please note that this salary range is specific to New York City, NY, and may vary in other locations. We encourage candidates to apply even if their salary expectations are outside of this range, as we are dedicated to finding the best fit for our team. #LI-Hybrid We are an E-Verify employer - all hired positions require successfully passing an E-Verify Check. Navigate the links below to learn more about careers at OdysseyRe. Life At OdysseyRe Workplace Initiatives A Rewarding Workplace Follow us on LinkedIn for company highlights ## At a glance - Posted by the employer: Sep 29, 2026 - First seen by OpenNash: Oct 11, 2026 - Last checked: Oct 18, 2026 - Listed for: 19 days - Location: Chicago, IL, US - Pay: $135,000 to $175,000[Apply on Fairfax Financial’s careers site →](https://careers.odysseygroup.com/job/New-York-Senior-Facultative-Underwriter-NY-10001/1424813700/) ## More jobs at Fairfax Financial ### [Actuarial Manager, Auto](https://jobs.opennash.com/companies/fairfax-financial/jobs/9ad679730674d2bf6672/) Chicago, IL, US ### [Commercial Auto, Program Manager](https://jobs.opennash.com/companies/fairfax-financial/jobs/dbd5436d28715a24e374/) Chicago, IL, US ### [2027 Summer Intern, Actuarial](https://jobs.opennash.com/companies/fairfax-financial/jobs/fb0ef06ef08672bb331a/) Stamford, CT, US ### [2027 Summer Intern, Underwriting](https://jobs.opennash.com/companies/fairfax-financial/jobs/425e5988e4d345ede068/) Stamford, CT, US ### [Actuarial Manager](https://jobs.opennash.com/companies/fairfax-financial/jobs/44487d1416bfe5d4d4d5/) New York, NY, US ## Similar jobs at other companies ### [Senior Property Facultative Underwriter](https://jobs.opennash.com/companies/swiss-re/jobs/a3facdd6107fd7c935ba/) Swiss Re · Chicago, IL, US ### [P&C Facultative Underwriter](https://jobs.opennash.com/companies/swiss-re/jobs/4d605f6e7dca2a12eb32/) Swiss Re · Bogota, CO ### [Senior Underwriter, Reinsurance Property Facultative](https://jobs.opennash.com/companies/axa-group/jobs/2a835cf1b9c05dcca463/) AXA Group · LOS ANGELES, United States ### [Underwriter, Property Facultative](https://jobs.opennash.com/companies/arch-capital-group/jobs/d7c9a8731a41dbccf3d7/) Arch Capital Group · New York, NY United States of America ### [Senior Underwriter, Property Facultative](https://jobs.opennash.com/companies/arch-capital-group/jobs/f0aabf0385656e2c1138/) Arch Capital Group · New York, NY United States of America OpenNash lists jobs from employers’ own careers sites and does not handle applications. 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