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Skyward Specialty Insurance is an A (Excellent) AM Best-rated specialty carrier operating exclusively in the E&S and specialty admitted markets. Our E&S Property Brokerage is 100% committed to the wholesale distribution channel - we build strategic relationships with producers who understand our appetite and depend on us for decisive, bespoke solutions on hard-to-place accounts.

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