Vice President - E&S Brokerage - Property

Skyward Specialty

8d•$235,000 - $270,000•Remote

About The Position

Skyward Specialty Insurance is seeking a Vice President - E&S Brokerage - Property. This senior leadership role is responsible for the strategy, profitability, and day-to-day management of Skyward's E&S Brokerage Primary & Excess Property book. The position involves leading a team of 10 underwriters and reporting directly to the President of E&S Property & Casualty and Inland Marine. This is a player-coach role, requiring the individual to set the underwriting vision, drive profitable growth, and remain hands-on with complex accounts, pricing discipline, and broker relationships. The company is an A (Excellent) AM Best-rated specialty carrier operating exclusively in the E&S and specialty admitted markets, committed to the wholesale distribution channel.

Requirements

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.
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.
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.

Responsibilities

Own the underwriting direction, risk appetite, and portfolio composition of the E&S Property (Primary & Excess) book across all target classes.
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.
Drive use of underwriting indications to enable broker partners to set accurate client expectations and accelerate decisioning.
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 areas for growth and tightening.
Balance profitable growth with underwriting discipline.
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.
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.
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.