The Head of E&S Property Underwriting is a senior leadership role responsible for the strategy, profitability, and day-to-day management of Skyward's E&S Brokerage Primary & Excess Property book. You will lead a team of 10 underwriters, reporting directly to the President of E&S Property & Casualty and Inland Marine. This is a player-coach role - you will set the underwriting vision and drive profitable growth while remaining hands-on with complex accounts, pricing discipline, and broker relationships.

Underwriting Leadership & Strategy

• Own the underwriting direction, risk appetite, and portfolio composition of the E&S Property (Primary & Excess) book across all target classes, including manufacturers, industrial, vacant, hospitality, healthcare, mercantile, and real estate schedules
• Set and enforce underwriting standards, pricing guidelines, and coverage parameters consistent with the book's profitability objectives
• Lead complex and large-account underwriting decisions; serve as the technical authority and escalation point for the team
• Maintain a disciplined approach to accumulation management, ensuring adherence to CAT exclusions (no Tier 1 Wind, Flood, or EQ/EQSL)
• Drive use of underwriting indications to enable broker partners to set accurate client expectations and accelerate decisioning

Portfolio Management & Profitability

• Monitor and actively manage loss ratios, combined ratios, and portfolio trends; take corrective action when segments underperform
• Partner with actuarial and finance on pricing adequacy, rate monitoring, and reserving inputs
• Analyze submission flow, hit ratios, and renewal retention to identify where the book is growing well and where it needs tightening
• Balance profitable growth with underwriting discipline - new premium is only valuable if it performs

Team Management & Development

• Lead, mentor, and develop a team of 10 property underwriters across experience levels
• Establish clear performance expectations, accountability frameworks, and a culture of continuous improvement
• Recruit and retain underwriting talent; build bench strength for future growth
• Foster a team environment that rewards technical rigor, sound judgment, and broker responsiveness

Wholesale Distribution

• Cultivate and deepen relationships with key wholesale broker partners; serve as a senior point of contact for strategic accounts
• Collaborate with production and distribution leadership to identify appetite gaps and market opportunities
• Represent Skyward at industry events, broker meetings, and wholesale market forums

Cross-Functional Collaboration

• Work closely with claims, actuarial, legal, and product teams to ensure the book is supported end-to-end
• Provide market and competitive intelligence to inform product development and pricing strategy
• Partner with technology and operations to improve submission handling, data quality, and underwriting workflow efficiency

Experience

• 10+ years of E&S or specialty property underwriting experience, with meaningful time in a wholesale/non-admitted environment
• Prior leadership experience managing underwriting teams; comfort operating as both a strategic leader and technical contributor
• Demonstrated track record of building or managing a profitable property book across a broad range of commercial classes

Technical Skills

• Deep knowledge of commercial property underwriting, including COPE analysis, rate-on-line assessment, and coverage structure
• Familiarity with layered property structures (ground-up, primary, quota share, and excess)
• Working knowledge of ISO and proprietary property forms
• Proficiency in evaluating equipment breakdown, property enhancement, and schedule risks
• Strong understanding of CAT modeling concepts and accumulation management principles

Leadership & Soft Skills

• Strong communicator and relationship builder - credible with both wholesale brokers and internal executive stakeholders
• Data-driven decision-maker with the ability to translate portfolio analytics into actionable strategy
• High accountability orientation; comfortable owning results and making hard calls on underperforming segments
• Collaborative and team-oriented, with the ability to develop talent and build a high-performance culture

Compensation & Benefits

The applicable base salary for this opportunity is $235,000 - $270,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives. We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance.

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