Skyward Specialty Insurance
10/07/2026  
This position is responsible for managing complex surety claims and providing legal support to underwriting and business leadership. Success requires strong surety claims experience, legal judgment, business acumen, and the ability to operate effectively in a fast-paced remote environment. Responsibilities – Independently adjust claims on complex contract and commercial surety bonds in multiple jurisdictions in a timely, thorough, and professional manner. Select, retain, and manage outside surety claims counsel and related resources (including consultants, accountants, expert witnesses, etc.) to effectuate best possible claim outcomes. Set well-reasoned reserves and control claims-handling costs and expenses Attend meditations, arbitrations and trials as needed and appropriate. Draft claim reports for UW & management. Assist in the creation or revision of surety claim and/or underwriting forms and documents as may be necessary. Assist underwriters with...
Skyward Specialty Insurance Remote, OR Full Time
09/17/2026  
Position Summary: This is an outstanding opportunity for a Senior Underwriter, specializing in Medical Malpractice, Healthcare Professional Liability, and General Liability for miscellaneous medical facilities (primary and excess), physicians and physician groups. Working both independently and part of a team to successfully manage their assigned book of business along with contributing to the overall profitability of the Healthcare Solutions business portfolio. This individual must be able to illustrate sufficient technical analysis, have a strong underwriting acumen combined with the necessary sales and marketing skills to achieve profitable growth targets. Essential Duties and Responsibilities: Produce, underwrite, manage and service a profitable book of new and renewal business.   Utilize underwriter authority in accordance with the published underwriting guidelines. Effectively negotiate and secure policy terms that align with the company directives...
Skyward Specialty Insurance Remote, OR Full Time
09/15/2026  
Skyward Specialty is seeking an experienced Senior Benefits Analyst to support the administration, compliance, and continuous improvement of our employee benefits and leave of absence programs. This role serves as a key subject matter expert for employee benefits, with a strong emphasis on multi-state leave administration. The ideal candidate brings deep experience managing complex leave programs across multiple states, including New York and New Jersey leave and disability requirements, while supporting a geographically dispersed workforce. In addition to leave administration, this role supports health and welfare benefits, retirement programs, vendor management, compliance, reporting, employee communications, and process improvement initiatives. The Senior Benefits Analyst partners closely with Human Resources, Payroll, Finance, Legal, and external vendors to deliver a compliant, efficient, and employee-focused benefits experience. Principal Duties and Responsibilities...
Skyward Specialty Insurance Houston, TX Full Time