2027 Summer Intern, Underwriting

Odyssey Group; Stamford (CT); Hybrid; USD 21,000 - 34,000; Full time

Job summary

OdysseyRe in Stamford, CT offers a 10-week underwriting internship program with rotations across Property Treaty, Casualty Treaty, and Facultative divisions. You will learn underwriting basics, work closely with client-facing teams, and present a final project to senior management.

Open to highly motivated undergraduate juniors with strong GPAs, excellent communication, and leadership potential. Hybrid role with in-office days and some travel to NYC.

Qualifications

• The program targets motivated undergraduates who are in their junior year and meet GPA and skill criteria.
• Internship rotates through Property Treaty, Casualty Treaty, Casualty Facultative, and other divisions.
• Interns engage with senior leaders and present learnings at program end.

Responsibilities

• Learn underwriting basics across divisions and markets.
• Rotate through multiple underwriting areas to gain broad exposure.
• Prepare and present a final project to senior management.

Skills

Presentation skills

Interpersonal skills

Analytical thinking

Leadership

Teamwork

Independent work

Education

GPA 3.2+

Undergraduate student, junior year

Job description

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Date: Sep 8, 2026

Location: Stamford, CT, US

Company: Odyssey

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.

The Company

OdysseyRe is the reinsurance arm of the Odyssey Group, a global insurance and reinsurance enterprise wholly owned by Fairfax Financial Holdings Limited. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance solutions through a network of branch and representative offices around the world. OdysseyRe’s Underwriting Division evaluates insurance risks on both a portfolio basis (Treaty reinsurance) and an individual risk basis (Facultative reinsurance). The principal responsibilities of an underwriter are to conduct an in-depth review of a Treaty or Facultative business opportunity by reviewing data and other relevant documents, determining the level of risk, and ultimately deciding if OdysseyRe should support the deal. Underwriters are client-facing and represent OdysseyRe in the market, working closely with reinsurance brokers and insurance company clients to negotiate transactions. In coordination with other departments to evaluate reinsurance opportunities, underwriters are the key revenue generators and the decisions they make are key to the Company’s performance.

The Opportunity

OdysseyRe’s Underwriting Internship Program is a 10-week rotational program offering a unique perspective of the reinsurance industry. As an intern, you will rotate through several underwriting divisions (Property Treaty, Casualty Treaty, Casualty Facultative, Accident and Health, etc.) to learn reinsurance basics, the day-to-day responsibilities of an underwriter, and the intricacies of each market. These foundational experiences will develop your technical skills and provide you with an understanding of our underwriting philosophy, which will endow you with the necessary skills to help underwrite new and renewal business. Several projects will be assigned during your rotations and the program will culminate with a presentation to senior management outlining your overall experience. If you are eager to learn and possess strong interpersonal skills, this is the role for you. You will engage with senior leaders daily and build your network at a variety industry events over the course of the summer.

Qualifications

The Underwriting Internship Program is open to highly motivated students who are in their junior year of an undergraduate program and meet the following criteria:

• GPA 3.2 and above
• Exceptional presentation and communication skills, both verbal and written
• Excellent interpersonal skills
• Analytical thinker with strong attention to detail
• Demonstrated leadership abilities through college or community activities
• Team-oriented with the ability to work independently

This is a hybrid role requiring 4 days in-office and 1 day remote each week, based out of our Stamford, CT office with occasional travel to New York City (approximately 20% of the time).

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Nearest Major Market: Bridgeport
Nearest Secondary Market: Danbury