Senior Underwriter - Property Facultative Reinsurance - Individual Risk -

Ascot Group•Chicago, IL

1d•Hybrid

About The Position

Ascot Group is seeking a detail-oriented, analytical underwriter to join its Property Facultative Reinsurance Team and support growth of the US Property Facultative Reinsurance division. The position involves account-level underwriting review and portfolio optimization to help ensure the profitability of the North American Property Facultative book while supporting business development. The underwriter will work with senior management, underwriters, and support staff, and will be expected to use AI-enabled tools confidently, apply sound judgment to their outputs, and adapt as technology evolves. The role may be filled at a different level depending on experience and includes 10–15% travel.

Requirements

Bachelor’s degree or equivalent experience.
At least 5 years of underwriting experience in the insurance industry.
Knowledge of Property Facultative insurance products, insurance regulations, and the insurance industry.
Strong collaborative skills and ability to thrive in a fast-paced, entrepreneurial environment.
Strong critical-thinking skills.
Excellent organizational, desk-management, and prioritization skills, with the ability to work independently and as part of a team.
Positive, self-motivated approach and strong interpersonal, communication, and presentation skills.
Strong technical, analytical, and quantitative skills.
Excellent oral and written communication skills, including the ability to negotiate successfully in difficult situations with agents and brokers.
Solution-oriented team player with strong relationship-management skills when working with internal and external stakeholders and customers.
Proficiency in Microsoft Office.

Nice To Haves

Property Facultative (Re)insurance underwriting experience is strongly preferred.
ARe, CPCU, ARM, or other relevant professional designation.

Responsibilities

Manage the profitability, growth, and retention of an assigned US-based Property Facultative Reinsurance book by executing property automatics underwriting and following the unit’s strategic plan.
Understand Ascot’s risk appetite and underwrite property reinsurance within designated underwriting authority.
Liaise with internal teams, including aggregate management, claims, compliance, and legal.
Participate in external underwriting audits for Ascot clients.
Build and maintain relationships with reinsurance peers, leaders, and internal partners to identify cross-selling opportunities.
Represent Ascot at appropriate market groups and committees.
Maintain knowledge of general market conditions.
Work with Assistants and take overall responsibility for account administration, including bordereau review, reporting deadlines, and premium reconciliation.
Develop and maintain broker relationships to market and sell Ascot’s products.
Embody The Ascot Way by fostering colleague engagement and development, collaboration, inclusivity, and individual accountability.
Perform other duties as assigned.

Benefits

Medical insurance, including prescription coverage
Dental insurance
Vision insurance
Health Savings Account
Commuter Account
Health Care and Dependent Care Flexible Spending Accounts
Life insurance
AD&D coverage
Work/Life Resources, including Employee Assistance Program
Paid holidays
Annual Paid Time Off, including paid state/local leave where required
Short-term disability
Long-term disability
Other leave benefits, including bereavement, FMLA, adoption, maternity, military, and primary and non-primary caregiver leave
Contributory 401(k) savings plan
Annual cash bonus and other forms of discretionary compensation may be awarded