Supervisor – Commissions and Collections

Windward Risk Managers

Supervisor – Commission and Collections managing commission payment processes and interactions with marketing, sales and operations teams. Responsible for accuracy and efficiency in handling transactions and agent inquiries.

Posted 8/1/2026full-timeBoca Raton • Florida • 🇺🇸 United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in commission and sales incentive administration, with strong analytical skills to evaluate complex payment processes and financial information. Proficient in MS Excel and Word for data analysis and reporting, while effectively collaborating with various departments to resolve issues.

Highest-signal resume keywords

Commission AdministrationSales Incentive ProcessingData AnalysisStrong Communication SkillsProcess Improvement

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Commission ProcessingFinancial ReportingData ReconciliationPayment Processing1099 ReportingAnalytical SkillsRecord MaintenanceSystem Enhancement IdentificationManual Commission StatementsComplex Problem Resolution

Soft Skills

Strong Organization SkillsCollaborationMentoringPlanning SkillsVerbal Communication

Tools & Technologies

MS ExcelMS WordPayment Processing SystemsData Management Systems

Industry Keywords

CollectionsSales IncentivesAgent CommissionFinancial InformationBusiness AdministrationAccountingFinance

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

Undergraduate degree in business administration, accounting, finance or related field
Proven experience (3+ years) in collections, commissions and/or sales incentive administration field
Strong verbal and written communication skills for interaction with agents in addressing agent inquiries
Strong analytical skills and ability to research and evaluate complex payment process issues and financial information
Strong organization and planning skills to set priorities, and to plan work
Ability to effectively operate with other departments and management to address challenges and collaborate to find solutions
Strong MS Excel and Word skills to prepare, analyze and properly present large sets of data

Benefits

Comp & perks

Hybrid schedule of 4 days in office and 1 day remote following initial training period
Training for up to 6 months fully in office 5 days per week