Skyward Specialty Insurance

SVP/VP – Accident & Health Actuary

Skyward Specialty Insurance

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $200,000 - $250,000 per year

Job Level

Lead

About the role

  • Provides actuarial leadership and strategic analytical support for Skyward Specialty’s A&H business, with a primary focus on stop loss and related health programs.
  • Responsible for pricing governance, reserving oversight, reinsurance analytics, underwriting decision support, regulatory rate filing support, and development of actionable portfolio insights.
  • Partners closely with Underwriting, Compliance, Finance, IT, Reinsurance partners, and external advisors in a public company / SOX-controlled environment.
  • Leads and develops a small actuarial team.
  • Influences across functions (Underwriting, Compliance, Finance, IT, Reinsurance) to ensure timely, controlled, and decision-useful actuarial outputs.
  • Provides actuarial support to Compliance for mid-year rate certifications and full-year rate filings, leveraging Willis Towers Watson stop loss manuals.
  • Maintains new business and renewal rate targets and rating tools within Connecture.
  • Maintains the Minimum Essential Coverage (MEC) rater.
  • Evaluates provider network savings and develops specific and aggregate pricing factors to support competitive and adequate pricing.
  • Develops and monitors key underwriting and portfolio performance metrics; presents findings to Underwriting leadership and Senior Staff.
  • Produces ad-hoc experience studies across business segments to inform strategy, pricing, and underwriting actions.
  • Supports Underwriting with complex case pricing and structure assessments, including consultation on unusual or high-exposure risks.
  • Evaluates and provides recommendations on AI-enabled medical underwriting solutions (e.g., Gradient, MedScore, Verikai, Milliman Curve), including validation of impact and governance considerations.
  • Models captive reinsurance structures and collaborates with captive actuaries and captive managers on design, performance, and ongoing monitoring.
  • Evaluates annual reinsurance rates and terms; maintains Excess of Loss (XOL) and Quota Share (QS) treaty structures within systems and governance processes.
  • Partners with Guy Carpenter to support the firm’s risk-based economic capital model, including data, assumptions, and business inputs.
  • Peer reviews claim liabilities and reserves; estimates and documents loss picks in accordance with internal controls.
  • Maintains alignment with SOX requirements and coordinates with external partners (e.g., CFGI and Ernst & Young) to support auditability, documentation, and controls testing.
  • Partners with IT to develop and maintain stop loss databases that support pricing, experience analysis, reserving, and reporting needs.
  • Maintains and enhances Core & Captive dashboards to provide transparent, timely portfolio intelligence to stakeholders.
  • Participates in and contributes to A&H and enterprise communication forums such as A&H Town Halls, Actuarial Summits, and Corporate Quarterly Business Reviews.

Requirements

  • FSA (Fellow of the Society of Actuaries) or ASA (Associate of the Society of Actuaries)
  • Significant actuarial experience supporting Accident & Health, with strong exposure to stop loss pricing and portfolio management.
  • Demonstrated experience operating in a public company environment with strong documentation discipline and comfort with SOX/internal controls.
  • Proven ability to lead a team and deliver through influence in a shared services model.
  • Strong business partnership skills with Underwriting, Finance, Compliance, IT, and reinsurance stakeholders.
  • Preferred Experience with Connecture rating tools and stop loss rater maintenance.
  • Experience with reinsurance treaty structures (XOL and QS) and captive arrangements.
  • Familiarity with economic capital modeling and working with reinsurance brokers/consultants.
  • Experience evaluating or implementing AI/insurtech underwriting tools and building governance around model usage.
Benefits
  • health and welfare benefits
  • tuition and professional certification assistance
  • 401k savings
  • elective participation in the Employee Stock Purchase Program
  • paid time off
  • paid holidays
  • child bonding leave
  • other employee assistance
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
actuarial leadershipstop loss pricingportfolio managementreinsurance analyticsunderwriting decision supportregulatory rate filingAI-enabled medical underwritingeconomic capital modelingcaptivesexperience studies
Soft Skills
team leadershipinfluencebusiness partnershipcommunicationanalytical supportcollaborationpresentation skillsdocumentation disciplinestrategic thinkingproblem-solving
Certifications
FSAASA