Vice President - E&S Brokerage - Property

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, quot