Job Description

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.

Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way.

The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric.

Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve for our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.

Ascot is embedding artificial intelligence (AI) and automation across the organisation to enhance decision‑making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI‑enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.

Position Overview:

We are seeking an experienced, growth-oriented Senior Underwriter, E&S Casualty – Complex Risk with strong wholesale broker relationships and expertise underwriting complex casualty risks. This role focuses on large, sophisticated accounts, including organizations with revenues exceeding $100 million and transportation risks with fleets exceeding 100 power units.

The Senior Underwriter will partner with wholesale brokers to evaluate, structure, and negotiate coverage solutions for new and renewal business. Working closely with internal and external stakeholders, you will deliver creative insurance solutions while maintaining underwriting discipline and profitability.

The ideal candidate will possess strong technical underwriting skills, sound judgment, and a proven ability to manage complex risks and broker relationships. Success in this role requires a customer-focused, detail-oriented, and results-driven professional who thrives in a fast-paced environment and contributes to the continued growth of the E&S Casualty Complex Risk portfolio.

Responsibilities:

• Build and manage a profitable Complex Risk portfolio through disciplined underwriting and execution of the business unit’s strategy.
• Underwrite and negotiate large, sophisticated casualty risks, including accounts with revenues exceeding $100M and transportation fleets exceeding 100 power units.
• Work independently within delegated underwriting authority and make referrals as required.
• Cultivate and maintain relationships with peers, leaders and internal partners across functional areas to identify cross-selling opportunities, assist in product development and operational excellence.
• Foster and maintain external relationships with wholesale brokers in an effort to market and sell Ascot’s products.
• Provide superior service to brokers and clients and create visibility through consistent engagement with trading partners.
• Work independently within delegated underwriting authority and make referrals as required.
• Stay current on competition, underwriting environment, market conditions and share that knowledge with colleagues and leadership.
• Perform other duties as assigned.
• Commit to The Ascot Way: Embody The Ascot Way in their daily interaction with colleagues, fostering colleague engagement and development, collaboration, inclusivity, and individual accountability.

Requirements:

• Bachelor’s Degree or equivalent experience.
• Minimum of 5 years of underwriting experience in the P&C insurance industry experience, with General Liability and Excess Liability preferred.
• Demonstrated experience working within the Complex Risk space of E&S Casualty.
• Deep knowledge of 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.
• Must be positive, self-motivated, and possess strong interpersonal, communication and presentation skills.
• Possess strong technical, analytical, and quantitative skills.
• Excellent oral and written communication skills, ability to successfully negotiate in difficult situations with agents and brokers.
• Solution oriented team player with a strong relationship management skill set working with both internal and external stakeholders and customers.
• Proficient in Microsoft Office.
• ASLI, CPCU, ARM or other relevant professional designation preferred, but not required.
• Ability to travel 10-15%.

***This position may be filled at a different level, depending on experience***

Compensation

Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot’s total compensation package for employees. Other rewards may include annual cash bonus and other forms of discretionary compensation awarded by the Company.

The annualized base pay range for this role is: $115,000 - $145,000.

Company Benefits

The Company provides a competitive benefits package that includes the following (eligibility requirements apply):

Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more

Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver)

Retirement Benefits: Contributory Savings Plan (401k)

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