Skyward Specialty Insurance

Financial Planning and Analysis

• Help business leaders make informed decisions by developing financial models, analyzing performance trends, summarizing key assumptions, and translating results into clear insights
• Partner and underwriting leaders on timely analysis that supports strategic priorities, including financial modeling of new business opportunities
• Build, maintain, and enhance reports, dashboards, and analyses within planning, financial reporting, Power BI, and other business intelligence tools to improve self-service analytics and reporting efficiency
• Develop analysis and presentation materials for quarterly business reviews with divisional leaders and Executive Management
• Prepare, review, and distribute quarterly profit and loss statements, including variance explanations, key business drivers, and opportunities to improve financial visibility

Senior Analyst, FP&A

Insurance

• Partner with the President of Reinsurance to shape and execute forward-looking reinsurance strategies that align with the company's growth, capital management, and enterprise risk objectives; contribute directly to board-level strategic discussions on reinsurance.
• Lead, mentor, and develop a team of reinsurance professionals to foster a high-performance culture focused on innovation, accountability, and excellence.
• Oversee the design, placement, and optimization of treaty and facultative reinsurance programs, including negotiations with reinsurers and brokers to achieve best-in-class outcomes.
• Direct and enhance contract review, drafting, and ongoing management processes to ensure alignment with underwriting objectives, regulatory compliance, and efficient claims recovery.
• Drive advanced analytics and reporting capabilities to assess reinsurance performance, emerging risks, and market opportunities. Prepare and present strategic insights and performance updates to the President of Reinsurance and, as appropriate, C-suite and board-level stakeholders.
• Cultivate and strengthen long-term partnerships with reinsurers, brokers, and industry bodies; serve as a company representative in the reinsurance market.
• Ensure all ceded reinsurance activities adhere to regulatory, accounting, and internal standards; support robust risk control, governance, and audit processes.
• Monitor industry developments, regulatory changes, and macroeconomic trends; represent the company at industry conferences and professional associations.

Vice President, Ceded Reinsurance

Director

• Manage all components of claim handling for the Management Liability line of business
• Independently review submitted materials and policy documents, perform complete coverage analysis, and prepare coverage determination correspondence
• Review and provide direction on reserve and settlement authority, where required, on complex, specialized claims
• Support business partners through communication about specific claims, identification of claim trends, input on development, and marketing support
• Monitor claim quality and customer feedback to ensure compliance with regulatory requirements, customer satisfaction and achievement of corporate objectives
• Operate within company guidelines and authority levels in the settlement of claims
• Make appropriate decisions on coverage and strategic settlement of claims
• Review and assign new files as needed

Claims Technical Director – Management Liability

Accountant

• Oversee the month end close and manage the preparation of monthly journal entries and account reconciliations
• Prepare and distribute monthly commission and reinsurance reports
• Prepare monthly transfers
• Review general ledger items for accuracy and completeness
• Review, analyze, report, and interpret financial reports
• Review, analyze and report claim payments
• Prepare monthly account reconciliations
• Assist with preparation of audit work papers
• Review reinsurance agreements and prepare settlements
• Perform various projects and analysis as required
• Work collaboratively with the actuary, underwriting and claims departments

Senior Accountant, Accident & Health

Auditor

• Review and validate medical stop loss aggregate claim reimbursements by auditing claim data, eligibility, plan provisions, and contract terms
• Audit aggregate stop loss submissions (weekly/monthly/quarterly/annual) to confirm accuracy
• Confirm appropriate treatment of: Coordination of Benefits (COB), subrogation, third-party recovery offsets, Provider credits/refunds, Rx rebates (if contractually relevant)
• Reconcile eligibility/enrollment counts
• Review Plan & Contract Interpret - Stop loss policy/certificate, endorsements, and amendments
• Communicate with underwriting, TPA’s, brokers/producers to resolve discrepancies

Claims Auditor – Stop Loss, Aggregate

Claims Specialist

• Handle claims nationwide reported under primary and excess Miscellaneous Professional E&O, including coverage analysis, investigation, liability and potential exposure analysis, and the development and implementation of resolution strategies.
• Effectively and promptly communicate with insureds, agents, brokers and underwriters regarding claim status and handling.
• Analyze coverage and prepare coverage letters on complex matters with the guidance of in-house coverage counsel.
• Manage claims in litigation, including strategizing with defense counsel and experts on defending such.
• Set timely and accurate indemnity and expense reserves and reevaluate/update reserves appropriately based upon claim development.
• Negotiate settlements and attend mediations, arbitrations and trials as appropriate.
• Manage and control Loss Adjusting Expenses incurred by counsel, experts and vendors.
• Present, analyze and make recommendations on reserves, coverage and strategy.
• Comply with state guidelines for Good Faith Claims Handling.
• Prepare required Large Loss Reports and Trial Alerts.
• Participate in professional liability industry organizations and instructional seminars for CE and CLE credits.
• Effectively communicate and interact with all internal and external stakeholders to promote a professional and positive business environment so that Skyward’s goals and objectives are being achieved.
• Other duties as may be required due to change, growth, and continuous improvement.

Senior Claims Adjuster, Professional Liability

• Help business leaders make informed decisions by developing financial models, analyzing performance trends, summarizing key assumptions, and translating results into clear insights
• Partner and underwriting leaders on timely analysis that supports strategic priorities, including financial modeling of new business opportunities
• Build, maintain, and enhance reports, dashboards, and analyses within planning, financial reporting, Power BI, and other business intelligence tools to improve self-service analytics and reporting efficiency
• Develop analysis and presentation materials for quarterly business reviews with divisional leaders and Executive Management
• Prepare, review, and distribute quarterly profit and loss statements, including variance explanations, key business drivers, and opportunities to improve financial visibility
• Promote a culture of personal responsibility/accountability and open communication

• Supports the Claims team by managing incoming claim-related correspondence
• Organizes electronic claim files
• Assists claims professionals with administrative and document preparation needs
• Sorts, orders, indexes, and files claim-related mail received via email
• Creates and organizes ImageRight folders/zip folders as needed to support claim file structure and accessibility
• Drafts documents and provides administrative and operational support to claims professionals
• Assists with special projects and other duties as needed due to business change and growth
• Participates in continuous claims process and operational improvement efforts, including identifying workflow efficiencies and supporting implementation of improvements

Claims Intake Specialist

Vice President

• Lead a team of 7 underwriters, reporting directly to the President of E&S Property & Casualty and Inland Marine
• Own the underwriting direction, risk appetite, and portfolio composition of the E&S Excess Liability book
• Set and enforce underwriting standards, attachment point discipline, coverage structure guidelines, and pricing parameters consistent with the book's profitability objectives
• Lead complex and large-account underwriting decisions; serve as the technical authority and escalation point for the team
• Maintain clear appetite boundaries — avoid invasive medical, NY Labor Law exposure
• Structure layered excess solutions above both occurrence and claims-made underlying policies
• Monitor and actively manage loss ratios, combined ratios, and portfolio trends by class and segment; take corrective action when performance deteriorates
• Partner with actuarial and finance on pricing adequacy, rate monitoring, and reserving inputs for an excess book
• Track submission flow, hit ratios, and renewal retention
• Manage premium concentration by class
• Lead, mentor, and develop a team of 7 excess liability underwriters

Vice President – E&S Brokerage – Excess

• Own the underwriting direction, risk appetite, and portfolio composition of the E&S Property book across all target classes
• Set and enforce underwriting standards, pricing guidelines, and coverage parameters consistent with the book's profitability objectives
• Lead complex and large-account underwriting decisions; serve as the technical authority and escalation point for the team
• Maintain a disciplined approach to accumulation management
• Monitor and actively manage loss ratios, combined ratios, and portfolio trends
• Partner with actuarial and finance on pricing adequacy, rate monitoring, and reserving inputs
• Lead, mentor, and develop a team of 10 property underwriters
• Cultivate and deepen relationships with key wholesale broker partners

Vice President – E&S Brokerage, Property

General

• Evaluate and underwrite transactional commercial surety submissions, including but not limited to motor vehicle dealer (MVD), license & permit, subdivision, court, contract-related transactional, mortgage broker, and specialty bonds.
• Analyze financial statements, credit reports, and supporting documentation to assess risk and determine appropriate terms, conditions, and pricing.
• Apply underwriting authority to approve, decline, or modify submissions in alignment with company guidelines and risk appetite.
• Ensure compliance with internal underwriting standards, regulatory requirements, and state-specific bond obligations.
• Manage a high volume of transactional submissions while maintaining strong turnaround times and service levels.
• Monitor and manage a book of business to ensure profitability, retention, and appropriate risk diversification.
• Identify opportunities for cross-selling and account expansion within existing agency relationships.
• Build and maintain strong relationships with agency partners to drive submission flow and grow market share.
• Communicate underwriting decisions effectively, including providing clear rationale and alternative solutions when appropriate.
• Negotiate terms, pricing, and commission structures to remain competitive while maintaining underwriting discipline.
• Act as a market-facing representative to support agency growth and retention initiatives.
• Support new business development efforts by identifying target agencies and producers within the transactional surety space.
• Participate in agency visits, industry events, and networking opportunities to strengthen relationships and increase brand presence.
• Maintain accurate documentation and records within underwriting systems.
• Ensure timely issuance of bonds, endorsements, renewals, and cancellations.
• Partner with internal teams (claims, legal, compliance, operations) as needed to support business objectives.

Commercial Surety Underwriter

Administration

• Serves as division specialist for Plan Document reviews, providing oversight to other A&H staff in this area and taking a lead in the reviews and acceptance of Plan Documents and amendments
• Corresponds with producer, broker, TPA, and/or underwriter to obtain information required for Plan Doc review
• Balances customer service, stop loss carrier requirements, and challenges associated with Plan Doc review
• Maintains all relevant electronic files, records, and databases
• Performs other duties as assigned

Sales Administrator – Policy Issue, Medical Stop Loss

• Provide analytical and operational support to Global Agriculture underwriting team
• Support underwriters in technical analysis of treaty reinsurance submissions
• Assist with pricing analyses and model input validation
• Monitor and analyze commodities markets
• Support daily execution and monitoring of options trading activity
• Assist in valuation and risk assessment of hedging positions
• Track CME Group futures and options markets
• Review primary policy and reinsurance contract wording
• Maintain submission logs and portfolio data
• Prepare and distribute reports in partnership with accounting and finance
• Respond to data requests from brokers and ceding company clients
• Monitor agriculture reinsurance market data

Analyst, Global Agriculture Reinsurance

• Own the day-to-day execution of Skyward's cost-containment program across the stop-loss portfolio
• Develop and refine cost-containment protocols, standard operating procedures (SOPs), and playbooks
• Monitor and evaluate cost-containment vendor performance
• Assist the VP with vendor selection, due diligence, and contract evaluation
• Track, quantify, and report cost-containment savings
• Stay current on emerging cost drivers, treatment modalities, regulatory changes, and market trends
• Provide senior-level clinical expertise on complex, high-cost, and sensitive claims
• Build and maintain executive-level relationships with TPAs, producers, policyholders, and cost-containment vendors
• Serve as a senior mentor and resource to Clinical Consultants
• Identify opportunities to leverage data and analytics to improve cost-containment outcomes
• Design and maintain SOPs, workflows, and documentation standards

Assistant Vice President – Cost Containment, Employer Stop-Loss

Manager

• Overseeing the company’s fraud detection, subrogation, and recovery functions
• Coordinating all potential fraud investigations and ensuring compliance with state-level SIU reporting requirements
• Using traditional and AI-based fraud detection indicators and other investigative tools
• Partnering with adjusters and claims managers to evaluate concerns, determine appropriate investigative strategies, and assign cases to third-party vendors
• Reviewing and interpreting claims data and data from third-party vendors to make recommendations for improvements in investigations, processes and outcomes
• Using ISO data and predictive models to proactively conduct and/or facilitate additional investigation on claims
• Assigning investigative fieldwork to third-party vendors and overseeing vendor performance, quality, and compliance
• Completing and/or contributing state-level SIU statistical reporting functions in conjunction with compliance department personnel
• Providing consultative support to claims staff regarding fraud detection, subrogation, and recovery opportunities
• Reviewing vendor investigative findings and preparing or validating reports summarizing conclusions and recommendations
• Coordinating with legal, compliance, underwriting, and law enforcement/regulatory agencies when necessary
• Developing and facilitating training and awareness initiatives to strengthen fraud prevention capabilities across the claims team
• Seeking out new vendors with insightful data sources and technology solutions that help identify fraud or questionable claim indicators
• Performing other duties as assigned.

Senior Analyst, FP&A

Vice President, Ceded Reinsurance

Claims Technical Director – Management Liability

Senior Accountant, Accident & Health

Claims Auditor – Stop Loss, Aggregate

Senior Claims Adjuster, Professional Liability

Senior Analyst, FP&A

Claims Intake Specialist

Vice President – E&S Brokerage – Excess

Vice President – E&S Brokerage, Property

Commercial Surety Underwriter

Sales Administrator – Policy Issue, Medical Stop Loss

Analyst, Global Agriculture Reinsurance

Assistant Vice President – Cost Containment, Employer Stop-Loss

Manager, Special Investigations – Recovery