Windward Risk Managers

General

• Configure rates, rules, and forms within the policy administration system (PAS) under supervision
• Monitor the Operations helpdesk, triage and escalate requests, and provide level-one helpdesk support
• Respond to technical assistance requests in person, by phone, or electronically
• Review business and regulatory requirements before making PAS configuration changes
• Analyze business systems and user needs
• Make approved PAS configuration changes and test functionality
• Fix product-configuration defects found during testing
• Perform peer reviews and quality testing on configuration changes
• Document requirements, use cases, and user stories
• Maintain knowledge-base documents
• Write and execute test plans and test scripts
• Follow code-deployment best practices using local repositories and pull/push/merge workflows
• Maintain records in JIRA, service desk, and Confluence
• Generate routine project status reports for management

Duck Creek Configurator II, III

Controller

• Manage and support day-to-day accounting activities, including Accounts Payable, Commissions, and Claims Billing functions
• Manage the GL Accounting team with month-end closing activities
• Produce company financial statements
• Support the Finance Controller with financial reporting, audits, budgeting, cost allocation, and internal controls
• Lead month-end closing and prepare internal monthly financial statements and packages
• Review journal entries, balance sheet reconciliations, and reports
• Work with the Commissions team to develop, analyze, and reconcile reports and statements
• Support Accounts Payable and Claims Billing functions as needed
• Train and mentor junior staff
• Assist with annual audit preparations
• Assist with system reviews for process and reporting improvements
• Lead the annual operating budget process with department heads
• Maintain detailed department-level budgets and supporting models
• Prepare monthly budget-to-actual variance analyses and identify key drivers and trends
• Partner with department leaders to review variances, validate explanations, and support corrective action
• Develop, document, and maintain cost allocation methodologies
• Ensure cost allocations are applied consistently and accurately
• Reconcile allocated costs to the general ledger and resolve discrepancies
• Periodically assess allocation methodologies

Assistant Controller

Collections

• Ensure commission or sales incentive payments have been properly processed
• Respond to escalated calls from the Marketing department regarding complex commission or sales incentive-related processing questions or problems
• Maintain appropriate records of communications with agents
• Prepare monthly/quarterly commission and sales incentive payment summary reports for agencies, or ad hoc reporting requests as needed
• Interact with agents to analyze and resolve non-routine/complex payment inquiries and disputes
• Process manual commission statements if required
• Resolve and reconcile individual transactions to the total of the statement and the cash receipt
• Coordinate with the Operations team regarding any system issues and work collaboratively with all stakeholders to find solutions and communicate resolutions
• Work collaboratively with staff and Marketing to identify and resolve any outstanding agent commission balances due to the company
• Assist with the development and implementation of process improvements
• Identify payment processing system enhancements
• Participate in other commission and sales incentive projects as needed
• Review and resolve any stale checks to agencies
• Assist with the preparation of agent 1099 commission reporting and respond to any follow-up inquiries from agents related to issues 1099s
• Navigate and pull data from multiple complex systems efficiently
• Apply funds received for balances due by agents to the company and deposit checks as/when applicable
• Identify and implement processes and procedures
• Create training materials to train and mentor staff
• May perform other responsibilities as assigned

Supervisor – Commissions and Collections

Business Analyst

• Partner directly with Underwriting, Product, Operations, Compliance, Claims, and Technology teams.
• Translate underwriting and/or claims guidelines into functional system requirements.
• Create user stories, business process flows, and requirement documentation.
• Troubleshoot system issues and coordinate resolution with IT and development teams.
• Participate in or lead requirements workshops, discovery sessions, and backlog refinement meetings.

Business Analyst I, II, III – Personal & Commercial Residential Insurance

• Work closely with staff and company’s Marketing, Sales and Operations teams to ensure transactional accuracy and enhance efficiency of commission payment process
• Responsible for follow-up commission questions from agents
• Process commission chargebacks related to agency of record transfers
• Ensure amounts due back to the company from agents are processed and applied timely and accurately
• Prepare monthly/quarterly commission and sales incentive payment summary reports
• Interact with agents to analyze and resolve non-routine/complex payment inquiries and disputes
• Process manual commission statements if required
• Coordinate with the Operations team regarding any system issues
• Work collaboratively with staff and Marketing to identify and resolve outstanding agent commission balances due to the company
• Assist with the development and implementation of process improvements
• Review and resolve stale checks to agencies
• Assist with preparation of agent 1099 commission reporting

Collections & Commissions Manager

• Ensure commission or sales incentive payments have been properly processed.
• Respond to escalated calls from the Marketing department regarding complex commission or sales incentive-related processing questions or problems.
• Maintains appropriate records of communications with agents.
• Prepares monthly/quarterly commission and sales incentive payment summary reports for agencies, or ad hoc reporting requests as needed.
• Interacts with agents to analyze and resolve non-routine/complex payment inquiries and disputes.
• Processes manual commission statements if required.
• Resolves and reconciles individual transactions to the total of the statement and the cash receipt.
• Coordinate with the Operations team regarding any system issues and work collaboratively with all stakeholders to find solutions and communicate resolutions.
• Work collaboratively with staff and Marketing to identify and resolve any outstanding agent commission balances due to the company.
• Assist with the development and implementation of process improvements.
• Identifies payment processing system enhancements.
• Participates in other commission and sales incentive projects as needed.
• Reviews and resolves any stale checks to agencies.
• Assist with the preparation of agent 1099 commission reporting and respond to any follow up inquiries from agents related to issued 1099s.
• Navigate and pull data from multiple complex systems efficiently.
• Apply funds received for balances due by agents to the company and deposit checks as/when applicable.
• Identify and implement processes and procedures.
• Create training materials to train and mentor staff.
• May perform other responsibilities as assigned.

Customer Support

• Manage escalated phone calls transferred by the front-line customer service team
• Analyze and make decisions on escalated endorsements
• Assess policy reinstatement opportunities for accounts canceled because of non-payment
• Respond to and triage emails from internal departments, making appropriate decisions
• Provide written responses to customer questions and concerns
• Assist in conducting quality reviews of customer service calls and related transactions
• Identify trends in customer service and processing issues, recommending procedural changes focused on retention and enhancing customer experience
• Evaluate system performance and suggest improvements to increase efficiency and effectiveness
• Provide operational support during severe weather events
• Perform other duties and projects as needed

Customer Service Escalation Specialist

Project Manager

• Develop and maintain project plans, schedules, milestones, dependencies, and deliverables.
• Actively track each team member’s planned and completed work, including commitments made during daily stand-ups and sprint planning.
• Develop a working understanding of the systems, applications, and business processes the team supports in order to effectively track progress, ask informed questions, and identify delivery risks or bottlenecks.
• Assist in defining project scope, managing changes, and coordinating resources across cross-functional teams to meet delivery commitments.
• Lead Scrum ceremonies including sprint planning, daily stand-ups, sprint reviews, and retrospectives as part of the project execution framework.
• Serve as a primary point of contact for project communications.
• Identify, document, and track project risks, issues, and dependencies.
• Maintain project documentation, schedules, and status reports.
• Support adherence to project management standards, processes, and governance requirements while ensuring alignment with Agile delivery practices.