Windward Risk Managers Jobs Hiring Now
Windward Risk Managers is hiring for 5 open roles on Migrate Mate as of July 16, 2026, concentrated in business operations and compliance & legal, with listed salaries up to about $109,000. Migrate Mate updates Windward Risk Managers's live openings daily. Windward Risk Managers is a specialty insurance services firm offering claims management, risk consulting, and investigative services to clients in the property and casualty insurance sector.
Find Windward Risk Managers JobsOverview
Windward Risk Managers hiring data on Migrate Mate, as of July 16, 2026.
- Open jobs
- 5
- Top team
- Business Operations
- Seniority
- Across all levels
- Work type
- 40% remote or hybrid
- Top location
- Boca Raton
- Salary range
- $68,000–$109,000
Listed salaries for Windward Risk Managers roles on Migrate Mate range from about $68,000 to $109,000 per year across 5 open roles, as of July 16, 2026. One role lists an hourly contract rate.
Open Roles at Windward Risk Managers
Showing 5 of 5+ Windward Risk Managers jobs
Florida Residency Requirement: Applicants must currently reside in the State of Florida to be considered for this position.
Schedule: This position follows an 11:00 AM–8:00 PM ET schedule and includes a shift differential.
Position Summary:
Join our team as a Customer Service Escalation specialist, where you will be responsible for reviewing and resolving escalated and complex customer concerns received via telephone, email, and other service requests. The ideal candidate will possess strong problem-solving and troubleshooting skills, as the position requires making decisions beyond standard guidelines. Please note this role is not part of the New Business/Renewal Underwriting Department
Essential Functions:
- 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
Required Education and Experience:
- Valid Florida Insurance License (2-20 or 20-44)
- High school diploma is required; college education is preferred
- Minimum of 5 years of current experience in Florida homeowners insurance, either in an agency or underwriting setting
Preferred Qualifications:
- Bilingual in English and Spanish is preferred
- Experience or education in training and procedural documentation is a plus
Essential Skills:
- Advanced knowledge of Florida homeowners coverage, industry challenges, and basic underwriting practices
- Demonstrated ability to analyze complex situations and make sound, strategic decisions.
- Exceptional attention to detail, particularly in complex or sensitive cases
- Proven ability to collaborate effectively across teams to resolve high-priority issues
- Excellent time management skills and the ability to adapt to changing priorities
- Strong work ethic and discipline, especially while working remotely
- Outstanding written communication skills, including excellent editing and proofreading abilities for professional correspondence
- Excellent oral and interpersonal communication skills, maintaining professionalism under stress and effectively engaging with various audiences
- Ability to demonstrate empathy while remaining objective
- A proactive mindset with a “can do” attitude
- Advanced proficiency in Microsoft Office, particularly Excel and Word
If you're a motivated professional with these qualifications, we invite you to submit your application.
Due to current business and operational considerations, we currently hire employees residing in the following states at this time: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, and WI.
Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future.
WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities.
Notice to Third Party Agencies: WRM does not accept unsolicited resumes from third party recruiting firms. Absent a signed Service Agreement by WRM’s Human Resources Department, WRM reserves the right to pursue and hire these candidates without financial obligation to recruiters or agencies.
Florida Residency Requirement: Applicants must currently reside in the State of Florida to be considered for this position.
Schedule: This position follows an 11:00 AM–8:00 PM ET schedule and includes a shift differential.
Position Summary:
Join our team as a Customer Service Escalation specialist, where you will be responsible for reviewing and resolving escalated and complex customer concerns received via telephone, email, and other service requests. The ideal candidate will possess strong problem-solving and troubleshooting skills, as the position requires making decisions beyond standard guidelines. Please note this role is not part of the New Business/Renewal Underwriting Department
Essential Functions:
- 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
Required Education and Experience:
- Valid Florida Insurance License (2-20 or 20-44)
- High school diploma is required; college education is preferred
- Minimum of 5 years of current experience in Florida homeowners insurance, either in an agency or underwriting setting
Preferred Qualifications:
- Bilingual in English and Spanish is preferred
- Experience or education in training and procedural documentation is a plus
Essential Skills:
- Advanced knowledge of Florida homeowners coverage, industry challenges, and basic underwriting practices
- Demonstrated ability to analyze complex situations and make sound, strategic decisions.
- Exceptional attention to detail, particularly in complex or sensitive cases
- Proven ability to collaborate effectively across teams to resolve high-priority issues
- Excellent time management skills and the ability to adapt to changing priorities
- Strong work ethic and discipline, especially while working remotely
- Outstanding written communication skills, including excellent editing and proofreading abilities for professional correspondence
- Excellent oral and interpersonal communication skills, maintaining professionalism under stress and effectively engaging with various audiences
- Ability to demonstrate empathy while remaining objective
- A proactive mindset with a “can do” attitude
- Advanced proficiency in Microsoft Office, particularly Excel and Word
If you're a motivated professional with these qualifications, we invite you to submit your application.
Due to current business and operational considerations, we currently hire employees residing in the following states at this time: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, and WI.
Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future.
WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities.
Notice to Third Party Agencies: WRM does not accept unsolicited resumes from third party recruiting firms. Absent a signed Service Agreement by WRM’s Human Resources Department, WRM reserves the right to pursue and hire these candidates without financial obligation to recruiters or agencies.
Job Roles at Windward Risk Managers
Working at Windward Risk Managers
Windward Risk Managers's 5 open roles are across all levels, and about 40% are remote or hybrid. The most active teams are business operations and compliance & legal. Windward Risk Managers provides claims management, field investigation, and risk consulting services within the property and casualty insurance industry. Open positions span analytical, technical support, project management, customer service, and field investigator functions, reflecting a staff that supports both operational and client-facing work. Most Windward Risk Managers roles are based in Boca Raton and Remote.
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Browse jobs by roleWindward Risk Managers Jobs: Frequently Asked Questions
How many jobs is Windward Risk Managers hiring for right now?
Windward Risk Managers is hiring for 5 open roles on Migrate Mate as of July 16, 2026, updated daily, concentrated in business operations and compliance & legal. Openings span claims analysis, technical support, project management, field investigation, and customer service. Migrate Mate refreshes Windward Risk Managers's listings every day, so checking back regularly surfaces newly posted positions.
What kinds of roles does Windward Risk Managers hire for?
The most active teams are business operations and compliance & legal. Windward Risk Managers posts roles across claims analysis, field investigation, IT help desk support, project management, and customer service escalation. Positions range from entry-level analyst roles to mid-level specialists and investigators, and most postings are across all levels. Both contract and permanent positions appear in the active listings.
Are Windward Risk Managers jobs remote or in-person?
A mix of remote and on-site. About 40% of Windward Risk Managers's open roles on Migrate Mate are remote or hybrid as of July 16, 2026, with the rest based in Boca Raton. Each Windward Risk Managers listing shows its work location so you can filter before applying.
How do I apply to a job at Windward Risk Managers?
Find a Windward Risk Managers role that matches your background on Migrate Mate, then follow the listing through to Windward Risk Managers' own application process. Windward Risk Managers manages its hiring directly, so all applications, screening steps, and interview scheduling are handled by their internal team. Migrate Mate does not accept applications on the company's behalf.
What do Windward Risk Managers jobs pay?
Listed salaries for Windward Risk Managers roles on Migrate Mate range from about $68,000 to $109,000 per year as of July 16, 2026, with most postings at across all levels. One role lists an hourly contract rate. Exact pay is set by Windward Risk Managers and shown on each listing.
Does Windward Risk Managers hire entry-level?
Most of Windward Risk Managers's open roles on Migrate Mate are across all levels as of July 16, 2026. Check individual Windward Risk Managers listings for stated experience requirements.
Where is Windward Risk Managers hiring?
Most Windward Risk Managers roles are based in Boca Raton and Remote, and about 40% offer remote or hybrid work as of July 16, 2026. Migrate Mate shows the location on each listing.