The SVP/VP – Accident & Health (A&H) Actuary 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. This role is responsible for pricing governance, reserving oversight, reinsurance analytics, underwriting decision support, regulatory rate filing support, and the development of actionable portfolio insights. The Chief Actuary partners closely with Underwriting, Compliance, Finance, IT, Reinsurance partners, and external advisors in a public company / SOX-controlled environment. Reporting & Leadership - Leads and develops a small actuarial team. - Influences across functions (Underwriting, Compliance, Finance, IT, Reinsurance) to ensure timely, controlled, and decision-useful actuarial outputs. Key Responsibilities Pricing, Rating & Regulatory Support - Provide actuarial support to Compliance for mid-year rate certifications and full-year rate filings, leveraging Willis Towers Watson stop loss manuals. - Maintain new business and renewal rate targets and rating tools within Connecture. - Maintain the Minimum Essential Coverage (MEC) rater. - Evaluate provider network savings and develop specific and aggregate pricing factors to support competitive and adequate pricing. Underwriting Partnership & Portfolio Insights - Develop and monitor key underwriting and portfolio performance metrics; present findings to Underwriting leadership and Senior Staff. - Produce ad-hoc experience studies across business segments to inform strategy, pricing, and underwriting actions. - Support Underwriting with complex case pricing and structure assessments, including consultation on unusual or high-exposure risks. - Evaluate and provide recommendations on AI-enabled medical underwriting solutions (e.g., Gradient, MedScore, Verikai, Milliman Curve), including validation of impact and governance considerations. Reinsurance & Capital Analytics - Model captive reinsurance structures and collaborate with captive actuaries and captive managers on design, performance, and ongoing monitoring. - Evaluate annual reinsurance rates and terms; maintain Excess of Loss (XOL) and Quota Share (QS) treaty structures within systems and governance processes. - Partner with Guy Carpenter to support the firm’s risk-based economic capital model, including data, assumptions, and business inputs. Reserving, Financial Controls & SOX Compliance - Peer review claim liabilities and reserves; estimate and document loss picks in accordance with internal controls. - Maintain alignment with SOX requirements and coordinate with external partners (e.g., CFGI and Ernst & Young) to support auditability, documentation, and controls testing. Data, Systems & Reporting Enablement - Partner with IT to develop and maintain stop loss databases that support pricing, experience analysis, reserving, and reporting needs. - Maintain and enhance Core & Captive dashboards to provide transparent, timely portfolio intelligence to stakeholders. Executive Communication & Culture - Participate in and contribute to A&H and enterprise communication forums such as A&H Town Halls, Actuarial Summits, and Corporate Quarterly Business Reviews. Qualifications Required - 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. Compensation & Benefits The applicable base salary for this opportunity is $200,000 - $250,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives.​ We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance.

• Lead product development and pricing for variable annuities and related guarantees (GLWBs and DBs) aligned with financial goals and risk appetite • Provide thought leadership on assumption setting (e.g., reinsurance, PBR margins, target surplus) and support enterprise assumption setting • Represent Pricing in ideation and feasibility processes to balance strategic impact and resource use • Oversee pricing projects, ensuring confidence in financial cash flow analysis (Statutory and GAAP) and risk assessment using GGY Axis • Maintain internal model controls and documentation in compliance with Pricing Standards • Present findings to senior management to inform business decisions and governance approvals • Collaborate with Product Management to ensure optimal data support for product initiatives • Lead ad hoc projects including product implementation, compliance, marketing support, and reinsurance • Guide actuarial recruiting and training to sustain a high-performance culture • Support acquisition due diligence and new business integration efforts • Foster a collaborative environment focused on professional growth and integrity in line with Actuarial Standards of Practice

• Lead full-cycle recruiting for specialized actuarial roles across pricing, reserving, forecasting, underwriting, and medical economics functions • Serve as a strategic recruiting advisor to actuarial and finance leaders • Influence business partners using data and market expertise • Build trusted relationships with hiring managers to understand business priorities and talent needs • Develop and maintain diverse pipelines for actuarial and finance roles • Own full-cycle recruiting ensuring a seamless candidate experience

• Build and maintain new efficient/expansive rating systems and related models in Python and in Excel. Building a system ultimately allows the team to help steer the portfolio more effectively • Build and maintain risk/simulation models to help analyze and steer the business • Research ways to leverage industry data to enhance current rating, new/current admitted filings, and provide guidance to underwriting • Develop complex analyses of our underwriting, operations, business development, product performance, and user experience • Assist the data science, operations, and insurance teams with ad hoc analysis, data normalization, data cleansing and process improvement • Support the integration and production of new data sources in a manner that minimizes development cycles while maximizing potential business applications • Continuously challenge how we can improve our underwriting and operations • Maintain a clean production environment such that the data models can be easily interpreted and built upon by other data science and engineering team members • Present your work, findings, and opinions to both technical and non-technical stakeholders.