Skyward Specialty

Role Description The objective of this position is to assist the Underwriter in the quoting process for our Medical Stop Loss business in the Accident & Health division. This position does not include binding authority. - Prepare new business submissions, including analysis of needed information for Underwriter review and quoting. - Customer service – correspond with clients requiring professional and responsive phone and email communications. - Process and maintain orderly electronic underwriting files. - Perform quality work within deadlines with or without direct supervision. - Interact professionally with other employees, customers, and suppliers. - Work effectively as a team contributor on all assignments. - Work independently while understanding the necessity for communicating and coordinating work efforts with other employees and organizations. - Adhere to company guidelines, policies, and procedures. - Other duties as may be assigned as the business continues to develop. Qualifications - Industry experience preferred - Proficiency in Microsoft Office product suite and the use of computer systems and various software applications - Collaboration and teamwork - Communication (verbal and written) - Organizational and planning skills - Analytical thinking and aptitude for evaluating and interpreting detailed information and data - Ability to independently multi-task and respond to changing business priorities - Demonstrated customer service experience and the ability to interact with a wide variety of people on a daily basis in person, via telephone, and email Benefits - The applicable base salary for this opportunity is $60,000 - $70,000. - The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. - This opportunity may be eligible for performance-based incentives. - 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 and paid holidays. - Child bonding leave. - Other employee assistance. Company Description

Role Description The Assistant Vice President OR Senior Underwriter, Global Agriculture Reinsurance is a senior technical underwriting role responsible for supporting, expanding, maintaining, and managing Skyward's global portfolio of agriculture reinsurance. The role underwrites and prices new and renewal treaty submissions, shapes portfolio strategy, and represents Skyward in the reinsurance market with brokers and ceding company clients. This is a high-authority individual-contributor position for a proven (re)insurance professional who is at their best evaluating complex treaty business, forming a defensible technical view of risk, and building durable broker and client relationships. The role can be filled at the Senior Underwriter or Assistant Vice President level depending on the candidate's experience and underwriting authority. It reports to the Head of Global Agriculture and partners closely with Actuarial, Claims, Finance, and Accounting. Key Responsibilities - Perform in-depth technical underwriting and analysis of treaty reinsurance business across the global agriculture portfolio, including proportional and non-proportional structures. - Underwrite and price new and renewal agriculture reinsurance submissions, applying delegated underwriting authority and pricing methodologies appropriate to crop, livestock, and related agricultural risks. - Review primary policy forms, reinsurance contract wording, and endorsements to confirm coverage intent, terms, and conditions are accurately reflected and aligned with Skyward's risk appetite. - Evaluate exposure, loss history, accumulation, and program structure to form a clear, defensible technical view of each opportunity. - Provide support for strategic planning and ongoing management of the global agriculture portfolio, including profitability monitoring, portfolio construction, and renewal strategy. - Market, develop, and maintain strong broker and ceding-client relationships, representing Skyward in the market and at industry events. - Monitor market development and explore trends and cycles in agriculture reinsurance, translating those insights into actionable recommendations. - Partner with Accounting, Finance, Claims, and Actuarial on monthly, quarterly, and ad hoc reporting and on reserving and planning processes. - Serve as a senior technical resource to analysts and less-experienced team members, contributing to underwriting guidelines, pricing tools, and best practices (AVP level). Qualifications - Bachelor's degree in agricultural economics, finance, risk management, actuarial science, mathematics, or a related field; advanced degree or professional designations (CPCU, ARe, ACAS/FCAS, or similar) a plus. - Seven or more years of (re)insurance experience, with a meaningful portion in agriculture, treaty reinsurance, or a closely related specialty line; calibrated toward the AVP end for candidates with broader portfolio or market-facing exposure. - Demonstrated treaty underwriting and pricing experience, including familiarity with proportional and non-proportional structures. - Working knowledge of agriculture insurance and reinsurance products and the global agriculture risk landscape. - Strong command of reinsurance contract and policy wording and the ability to identify coverage and structural issues. - Proficiency with pricing and exposure analysis tools and strong Excel skills; comfort working with large data sets. - Established broker and/or cedant relationships and the credibility to represent Skyward in the market. - Excellent analytical, communication, and relationship-management skills, with sound, decisive underwriting judgment. Travel This role involves periodic domestic and international travel for client and broker meetings, industry conferences, and market events (estimated 15–25%). Compensation & Benefits - The applicable base salary for this opportunity is $125,000 - $175,000. - 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.

Role Description The Senior Underwriter OR AVP is responsible for underwriting new and renewal medical stop-loss captive accounts at a profitable level. This role involves managing relationships with producers and customers to ensure alignment with overall company stop-loss goals. The Senior Underwriting position works closely with the other team members in the region and with the sales team to identify business and producers that most closely meet our underwriting acumen. - Evaluate risk for in-force business and new business prospects. - Make decisions to quote or decline to quote and develop premium rates in accordance with underwriting guidelines and authority limits. - Develop and communicate new business or renewal rate recommendations and decisions in line with underwriting authority limits. - Prepare and generate correspondence, proposals, and other reports as needed. - Provide detailed explanations to Skyward A&H clients regarding conditions and requirements of quotes, rating decisions, and other information to support the sale of new and renewal business. - Coordinate medical reviews with the clinical risk management team and make recommendations regarding the level of acceptable risk. - Negotiate rates, terms, and conditions for new and existing business. - Manage the new business and renewal book to balance profitability and growth. - Process sold accounts and confirmed renewals following established procedures. - Develop and maintain relationships with clients, producers, and sales representatives to support the company’s production goals and persistency. - Support Skyward A&H growth initiatives related to reference-based pricing, captive, and small group programs. - Review plan design and calculate rates for requested or recommended plan changes. - Provide competitive feedback on rates, products, pricing, and marketing strategies. - Make presentations to peers, producers, and leadership as necessary. - Utilize departmental tools, experience, and judgment during the underwriting process to set pricing, review risk, negotiate, and accomplish goals. - Assist associate underwriters with training and peer review. - Perform other duties as assigned. - Some travel may be required for trainings and/or meetings (less than 10%). Qualifications - Bachelor’s Degree preferred. - 4+ years of experience underwriting medical stop-loss required. - Preferred experience underwriting reference-based pricing and/or small group programs. - Professional certifications (HIAA, CEBS, FMLI, etc.) beneficial. Requirements - In-depth knowledge of underwriting principles, risk assessment, and regulatory requirements. - Proven track record of developing and implementing successful underwriting strategies and policies. - Strong analytical and decision-making skills, with the ability to evaluate complex transactions. - Ability to prioritize and balance a dynamic workload. - Strong communication and interpersonal skills, with the ability to build relationships with internal and external stakeholders. - Proficiency in underwriting software (Connexure/ESL preferred) and other relevant technology. Benefits - The applicable base salary for this opportunity is $100,000 - $170,000. - The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. - This opportunity may be eligible for performance-based incentives. - 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 and paid holidays. - Child bonding leave. - Other employee assistance.

Role Description The Senior Underwriter OR AVP is responsible for underwriting new and renewal medical stop-loss accounts at a profitable level. This role involves managing relationships with producers and customers to ensure alignment with overall company stop-loss goals. The Senior Underwriting position works closely with the other team members in the region and with the sales team to identify business and producers that most closely meet our underwriting acumen. - Evaluate risk for in-force business and new business prospects. - Make decisions to quote or decline to quote and develop premium rates in accordance with underwriting guidelines and authority limits. - Develop and communicate new business or renewal rate recommendations and decisions in line with underwriting authority limits. - Prepare and generate correspondence, proposals, and other reports as needed. - Provide detailed explanations to Skyward A&H clients regarding conditions and requirements of quotes, rating decisions, and other information to support the sale of new and renewal business. - Coordinate medical reviews with the clinical risk management team and make recommendations regarding the level of acceptable risk. - Negotiate rates, terms, and conditions for new and existing business. - Manage the new business and renewal book to balance profitability and growth. - Process sold accounts and confirmed renewals following established procedures. - Develop and maintain relationships with clients, producers, and sales representatives to support the company’s production goals and persistency. - Support Skyward A&H growth initiatives related to reference-based pricing, captive, and small group programs. - Review plan design and calculate rates for requested or recommended plan changes. - Provide competitive feedback on rates, products, pricing, and marketing strategies. - Make presentations to peers, producers, and leadership as necessary. - Utilize departmental tools, experience, and judgment during the underwriting process to set pricing, review risk, negotiate, and accomplish goals. - Assist associate underwriters with training and peer review. - Perform other duties as assigned. - Some travel may be required for trainings and/or meetings (less than 10%). Qualifications - Bachelor’s Degree preferred. - 4+ years of experience underwriting medical stop-loss required. - Preferred experience underwriting reference-based pricing and/or small group programs. - Professional certifications (HIAA, CEBS, FMLI, etc.) beneficial. Requirements - In-depth knowledge of underwriting principles, risk assessment, and regulatory requirements. - Proven track record of developing and implementing successful underwriting strategies and policies. - Strong analytical and decision-making skills, with the ability to evaluate complex transactions. - Ability to prioritize and balance a dynamic workload. - Strong communication and interpersonal skills, with the ability to build relationships with internal and external stakeholders. - Proficiency in underwriting software (Connexure/ESL preferred) and other relevant technology. Benefits - The applicable base salary for this opportunity is $100,000 - $170,000. - The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. - This opportunity may be eligible for performance-based incentives. - 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 and paid holidays. - Child bonding leave. - Other employee assistance.

Role Description The E&S General Liability Senior Underwriter OR AVP is responsible for underwriting new and renewal middle market accounts within an E&S/non-admitted environment. This role requires strong technical underwriting judgment, thoughtful risk selection, and the ability to structure coverage/terms to achieve profitable growth. The Senior Underwriter should have established wholesale broker relationships with individual brokerage offices. The Senior Underwriter will independently manage a renewal book, grow new business through select wholesale broker relationships, and provide mentorship and technical guidance to underwriting team members. Essential Duties and Responsibilities - Underwrite and manage a middle market GL portfolio including new business, renewals, and account stewardship to achieve profitability, retention, and growth objectives. - Evaluate risk and exposure by analyzing operations, loss history, financials (as appropriate), coverage needs, and industry trends; determine suitability within company appetite. - Develop coverage, pricing, and terms aligned with risk characteristics and rate adequacy; leverage deductibles/SIRs, endorsements, and coverage restrictions when needed to achieve appropriate risk-adjusted return. - Structure and negotiate deals with wholesalers, including quote development, proposal presentation, counteroffers, and binding decisions within delegated authority. - Oversee account lifecycle management, including: - underwriting file documentation (analysis, rationale, pricing support, referrals), - issuance coordination and policy review, - mid-term endorsements, - renewal strategy and execution, - collaboration with claims, loss control, and operations as applicable. - Maintain excellent underwriting governance: ensure compliance with guidelines, regulatory/non-admitted requirements, documentation standards, and referral/authority protocols. - Broker relationship management and marketing: manage a targeted group of wholesale brokers, actively source and qualify middle market opportunities, communicate underwriting appetite clearly and consistently, differentiate through expertise, responsiveness, and creative problem solving—not price alone. - Portfolio management: monitor aggregates, concentration, mix of business, and loss trends, identify remediation actions on underperforming segments/accounts, contribute to planning and forecasting efforts. - Mentor and support junior underwriters: provide technical coaching, file guidance, and decision support, participate in training, peer reviews, and knowledge sharing. - Contribute to underwriting discipline and continuous improvement: assist in refining guidelines, workflows, tools, and product/coverage approach for middle market GL, support underwriting file audits/reviews and participate in system testing/enhancements as needed. Qualifications - Bachelor’s degree required (or equivalent experience). - 5+ years of General Liability underwriting experience, with demonstrated success underwriting E&S/non-admitted business. - Experience underwriting middle market accounts with higher complexity (e.g., multi-location, multi-state, higher hazard classes, layered or manuscript coverage considerations, heavier loss history, complex operations). Requirements - Strong technical knowledge of GL coverage, policy forms, exclusions/endorsements, and non-admitted market practices. - Demonstrated ability to assess risk, analyze data, and make sound decisions with clear underwriting rationale. - Strong command of pricing concepts and rate adequacy, including using terms/structure (not just price) to appropriately underwrite risk. - Proven ability to build and maintain wholesale broker relationships and to generate profitable submissions. - Excellent communication skills—able to explain decisions and coverage positions clearly to brokers and internal partners. - Ability to work independently while collaborating effectively across underwriting, claims, loss control, and operations. - Strong organizational skills and attention to detail; able to manage multiple accounts and deadlines in a fast-paced environment. Preferred / Beneficial Qualifications - Insurance designations (e.g., CPCU, AU, ARM, RPLU) preferred. - Experience with specific middle market segments relevant to your appetite (e.g., construction, habitational, products, light manufacturing, distribution, social services, etc.). - Proficiency in Microsoft Office Suite (Outlook, Word, Excel) and underwriting systems/analytics tools. - Experience participating in audits/file reviews, guideline creation, or product refinement. Compensation & Benefits - The applicable base salary for this opportunity is $120,000 – $170,000. 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 offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401(k) savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance programs.

Role Description Responsible for underwriting new/renewal general liability accounts at a profitable level and managing the relationships involved to ensure the alignment with overall company goals. Participate in the training and development of underwriting team members. Collaborate with team members to improve decision making, risk selection, terms, product and workflow. - Complete proper file documentation including loss analysis, exposures to loss, rate adequacy and use of available information. - Oversee all aspects of accounts, including risk selection, quoting, binding, issuance, file documentation, loss control report review, review of mid-term endorsements and renewals as well as billing, servicing, and claims, whether duties are to be performed by you or by others acting under your direction. - Develop and manage brokers including marketing visits and periodic review of loss results, submission activity, and productivity. - Assist in analyzing and developing new products, pricing, or coverage as needed. - Assist in analyzing loss trends. - Mentor less experienced team members. - Remain current on industry issues and insurance marketplace news that could impact the success of the company and the achievement of its goals and objectives. - Conduct underwriting file reviews on a rotating basis to confirm underwriters are operating within their delegated authority set forth by company guidelines and within confines of company reinsurance treaties. Qualifications - Bachelor’s Degree preferred - Insurance designations or certifications preferred - 6+ years’ experience in casualty underwriting required Requirements - Ability to apply principles of logical thinking to assess risk, define problems, collect data, establish facts, and draw intelligent, valid conclusions and make decisions. - Ability to work both independently and collaboratively in a team environment to develop and manage a book of business that achieves corporate financial objectives. - Sound knowledge of general liability rating techniques and policy forms in a non-admitted carrier environment, including the value of coverage restrictions compared to price. - Ability to differentiate oneself based on service and risk appetite rather than price. Benefits - The applicable base salary for this opportunity is $120,000 - $170,000. - 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 programs.

Role Description The Assistant Vice President OR Senior Underwriter (Based on experience) underwrites and markets complex insurance products primarily through Wholesale brokerage, managing the relationships involved to ensure profitable alignment with overall company goals and provides intermediate levels of risk assessment and technical underwriting expertise to determine underwriting acceptability. Additionally, provides guidance and support to less experienced team members. - Underwriting new and renewal accounts to meet growth and profitability targets. - Negotiating participation, pricing and terms and conditions with brokers. - Responsible for effective management of assigned distribution, including maintaining existing relationships as well as identifying and developing new distribution. - Foster strong partnerships by keeping brokers informed of new products, programs and overall appetite while also communicating underwriting decisions in a clear and timely manner. - Research and obtain market intelligence in order to stay on top of emerging risks, industry trends and competitor activities. - Assist in analyzing and developing new products, pricing, or coverage as needed. Assist in analyzing loss trends. - Adheres to CAT guidelines and underwriting discipline to minimize exposure and appropriately price individual risks. - Remain current on industry issues and insurance marketplace news that could impact the success of the company and the achievement of its goals and objectives. Qualifications - Bachelor’s degree preferred. - 5+ years of progressively complex specialty underwriting experience required. - Experience in the wholesale E&S Inland Marine market required. - Upper tier middle market and Large Account experience utilizing complex program designs required. - CPCU/ RPLU designation is a plus. - Ability to apply principles of logical thinking to assess risk, define problems, collect data, establish facts, and draw intelligent, valid conclusions and make decisions. - Familiarity with CAB, CATNET, and other peril or risk based decision support tools. - Sound knowledge of AAIS Forms, manual rating techniques, and manuscript forms in a specialty carrier environment, including the value of coverage restrictions compared to price. - Ability to differentiate oneself based on service, product knowledge, and risk appetite rather than price exclusively. Benefits - The applicable base salary for this opportunity is $115,000 - $195,000. - The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. - This opportunity is eligible for performance-based incentives. - 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 and paid holidays. - Child bonding leave. - Other employee assistance programs.

Role Description The Senior Underwriter OR AVP is responsible for underwriting new and renewal medical stop-loss accounts at a profitable level. This role involves managing relationships with producers and customers to ensure alignment with overall company stop-loss goals. The Senior Underwriting position works closely with the other team members in the region and with the sales team to identify business and producers that most closely meet our underwriting acumen. - Evaluate risk for in-force business and new business prospects. - Make decisions to quote or decline to quote and develop premium rates in accordance with underwriting guidelines and authority limits. - Develop and communicate new business or renewal rate recommendations and decisions in line with underwriting authority limits. - Prepare and generate correspondence, proposals, and other reports as needed. - Provide detailed explanations to Skyward A&H clients regarding conditions and requirements of quotes, rating decisions, and other information to support the sale of new and renewal business. - Coordinate medical reviews with the clinical risk management team and make recommendations regarding the level of acceptable risk. - Negotiate rates, terms, and conditions for new and existing business. - Manage the new business and renewal book to balance profitability and growth. - Process sold accounts and confirmed renewals following established procedures. - Develop and maintain relationships with clients, producers, and sales representatives to support the company’s production goals and persistency. - Support Skyward A&H growth initiatives related to reference-based pricing, captive, and small group programs. - Review plan design and calculate rates for requested or recommended plan changes. - Provide competitive feedback on rates, products, pricing, and marketing strategies. - Make presentations to peers, producers, and leadership as necessary. - Utilize departmental tools, experience, and judgment during the underwriting process to set pricing, review risk, negotiate, and accomplish goals. - Assist associate underwriters with training and peer review. - Perform other duties as assigned. - Some travel may be required for trainings and/or meetings (less than 10%). Qualifications - Bachelor’s Degree preferred. - 4+ years of experience underwriting medical stop-loss required. - Preferred experience underwriting reference-based pricing and/or small group programs. - Professional certifications (HIAA, CEBS, FMLI, etc.) beneficial. Requirements - In-depth knowledge of underwriting principles, risk assessment, and regulatory requirements. - Proven track record of developing and implementing successful underwriting strategies and policies. - Strong analytical and decision-making skills, with the ability to evaluate complex transactions. - Ability to prioritize and balance a dynamic workload. - Strong communication and interpersonal skills, with the ability to build relationships with internal and external stakeholders. - Proficiency in underwriting software (Connexure/ESL preferred) and other relevant technology. Benefits - The applicable base salary for this opportunity is $100,000 - $170,000. - The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. - This opportunity may be eligible for performance-based incentives. - 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 and paid holidays. - Child bonding leave. - Other employee assistance.

Summary This position is responsible for building strong relationships with our internal customers by being a thought leader supporting various segments and divisions. Excellent communication, customer service and organizational skills are required for success in this position. This role involves approaching problems with a holistic perspective, focusing not just on resolving the immediate issue but also on identifying sustainable and innovative ways to achieve long-term success. The candidate will have excellent analytical skills, and the ability to communicate effectively with technical and non-technical stakeholders. Principal Duties and Responsibilities - Responsible for developing and maintaining trusted business relationships, driving the greatest possible business value from technology to meet the business needs and organizational goals. - Apply influential analytical and problem-solving skills to communicate solutions in both technical and user-friendly language. - Collaborate in the planning, designing, development, and deployment of new applications and enhancements to existing applications ensuring full systems lifecycle process is adhered to. - Work with business stakeholders and project managers to develop business requirements and project implementation strategies. - Collaborate with customers, vendors, developers, architects, QA and other technical teams to design, test, and implement solutions that meet customer requirements. - Key aspect of this role is comprehensive requirements gathering, cross-functional collaboration, and leveraging cutting-edge technologies. - Promote a proactive environment by researching and recommending process and technology solutions for continuous improvement. - Develop test cases, perform testing, and manage user testing to ensure requirements are met for system modifications. - Demonstrate products, leveraging a combination of technical expertise, business acumen, and excellent communication skills to showcase how solutions align with business needs and objectives. - Generate weekly and monthly reports and perform data analysis to identify anomalies, trends, and improvement opportunities. - Analyze and resolve Helpdesk issues. - Mentor and coach analysts team members ​Knowledge, Skills, and Abilities - A curious and analytical mindset focused on finding solutions to difficult problems. - Strong documentation and organizational skills are necessary. - To exhibit a confident, engaging communication style incorporating both written and verbal communication skills. - Excellent analytical and problem-solving skills. - Experience/Knowledge of Commercial Insurance and/or Underwriting or Claims systems. - Experience in developing business and functional requirements. - Ability to multitask in a fast-paced environment at various stages of completion. - Ability to translate highly technical specifications into clear non-technical requirements and functional design documents - Advanced skills in Microsoft Office applications, specifically SharePoint, Word, Excel, and Outlook. Visio and Power BI skills are a plus. - Exposure to Azure DevOps, Power Automate and Power Apps a plus. - Familiarity with modern AI-powered productivity tools such as GitHub Copilot, ChatGPT, or similar technologies preferred. - Commitment to staying updated on advancements in AI tools and best practices. Qualifications, Education and Experience - 4-year college degree and/or 10+ years of work experience as a Business Analyst required - 3+ years P&C Insurance industry experience highly preferred - Permanent US Work Authorization required - Experience with Agile, Iterative and Waterfall project methodologies Compensation & Benefits The applicable base salary for this opportunity is $105,000 - $130,000. 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 programs. #LI-Remote

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.