Casualty Underwriting Director – Houston​/Chicago​/Boston

Position Summary

Cross Cover Insurance Services is an underwriting‑driven, tech‑enabled MGA platform, who is seeking an entrepreneurial specialty underwriter to build and lead casualty lines. As a member of the Cross Cover senior management team, the Underwriting Director – Casualty will serve as the organization’s strategic leader for underwriting strategy, risk management, pricing integrity and performance of the casualty portfolio. This role is accountable for setting underwriting philosophy driving strategic initiatives / product development and managing underwriting performance in alignment with corporate objectives.

The ideal candidate will possess a strong entrepreneurial spirit to build something new and willingness to embrace technology to drive efficiency and value across the underwriting value chain. We are looking for a visionary leader with deep technical expertise, strong surplus lines market presence, and a proven track record of building and scaling profitable cross‑cycle specialty insurance businesses. While we are open to exploring any specialty line that can add value to our carrier partners, we are currently actively pursuing those with backgrounds in Commercial GL and Excess Liability.

• Lead all aspects of casualty product creation, including defining underwriting strategy, establishing risk tolerance and pricing targets ensuring alignment with the company’s risk appetite and profitability goals.
• Attract, maintain and enhance strategic relationships with carrier markets, key wholesale brokers and national distribution partners.
• Deliver top and bottom‑line business plan, supported by rigorous monitoring and evaluation of underwriting quality, exposures, rating, performance and profitability in coordination with the Group CUO.
• Build, mentor, and lead a high‑performing underwriting team with strong analytical and decision‑making capabilities.
• Consistently pursue opportunities to differentiate Cross Cover in the industry through our offerings and how we conduct business.

• Establish and enforce consistent underwriting best practices including development of underwriting guidelines, pricing methodologies and authorities grants to ensure consistent risk selection and portfolio performance.
• Coordinate / facilitate / lead new business, renewals, re‑pricings, restrictions, special acceptances, commutations, and cancellations in determining risk acceptability & coverage, in accordance with established underwriting guidelines and authorities.
• Create and implement governance framework, audit processes, and performance metrics to ensure underwriting best practices and portfolio health.
• Lead portfolio reviews to assess risk exposure, concentration, and underwriting profitability.
• Continuously evaluate underwriting processes and technology to drive automation, efficiency, and scalability of the casualty portfolio.

• Implement key performance indicators and dashboards to monitor performance, financial results, risk exposure that will enable underwriters to make better decisions regarding deployment of the firm’s capital.
• Ensuring appropriate systems and controls are in place and adhered to for the monitoring of underwriting activities, including exposure, income and aggregates in alignment with Group.
• Use analytics and data driven insights to evaluate underwriting performance, identify trends and emerging issues to guide pricing and portfolio strategy.
• Optimize allocation of capacity across regions, sub‑products, and segments to highest margin opportunities.
• Drive portfolio diversification initiatives to monitor exposure to emerging risks and loss trends and ensure proactive mitigation strategies.

• A minimum of 15+ years of progressive experience in the casualty insurance industry with significant focus on specialty lines, E&S, or program business. At least 10 years of proven leadership experience with a proven track record of building and growing profitable portfolios.
• A robust knowledge of US casualty insurance market, combined with…