Jobs at Skyward Specialty Insurance

Manages and grows a profitable portfolio of captive insurance programs, including opportunity evaluation, underwriting governance, risk referrals, pricing, product development, and partner relationships. Tracks performance metrics, conducts audits, develops guidelines, coordinates with actuarial and operational teams, and reports recommendations to senior leadership. Requires property and casualty underwriting expertise, captive experience, knowledge across multiple P&C lines, and travel of up to 25%.

Directs the company-wide internal audit function, overseeing SOX and MAR compliance, risk assessments, audit planning, control testing, remediation, segregation-of-duties reviews, external auditor coordination, and fraud investigations. The role develops internal controls, maintains audit documentation, supports regulatory compliance, trains employees, and leads continuous improvement initiatives across business functions.

Manages complex contract and commercial surety claims across multiple jurisdictions, including claim adjustment, reserves, litigation coordination, outside counsel management, and reporting. Supports underwriting with bond, indemnity, and collateral agreements; researches legal developments; and develops training and legal resources for underwriting and company staff.

Administer and improve employee benefits and multi-state leave programs, serving as a subject matter expert on FMLA, ADA, disability, and state leave requirements. Manage enrollments, vendors, audits, reporting, payroll coordination, compliance, employee communications, and open enrollment. Analyze benefits and leave data, resolve complex cases, and partner with HR, Payroll, Finance, Legal, and external administrators to support a compliant, efficient benefits experience.