Demo

Customer Service Escalation Specialist (Mid-Day Shift)

Windward Risk Managers
Boca Raton, FL Full Time
POSTED ON 3/14/2026
AVAILABLE BEFORE 4/30/2026
  • This position will have a schedule of 11AM - 8PM ET shift differential ****

Position Summary

We are seeking a dedicated Customer Service Escalation Specialist to join our team. This role involves managing escalated and complex customer matters received through phone calls, emails and processing 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

  • Handle escalated phone calls referred by the front-line customer service team
  • Research and make decisions on escalated endorsements
  • Assess and determine reinstatement for policies canceled due to 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
  • Identify opportunities for system improvements and provide actionable recommendations
  • Offer support during catastrophic weather events as needed
  • Perform other duties and projects as assigned

Qualifications

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
  • Strong analytical and critical thinking skills with the ability to think strategically
  • 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 meet these qualifications and are ready to take on new challenges in a dynamic environment, we encourage you to apply!

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.

Salary : $23 - $26

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