Careers
Join our Team
At Windward Risk Managers our team members are integral to our success. We’re committed to delivering high-quality services to our insureds in all we do. If you're interested in being part of our team, consider applying for one of our available positions.

Why Join Windward Risk Managers?
At Windward Risk Managers, we’re not just building a company – we’re shaping the future of insurance management. As the trusted partner behind Florida Peninsula Insurance Company, Edison Insurance Company, and Ovation Home Insurance Exchange, we’re committed to driving innovation in the insurance industry while staying true to our values of integrity, collaboration, and excellence.
Our approach combines data-driven decision-making with a people-first mindset, ensuring we remain agile in an evolving marketplace. With a focus on long-term success, we’re poised for growth and excited to explore new opportunities, both within Florida and beyond.
When you join Windward, you become part of a forward-thinking team redefining what’s possible in insurance. Together, we’re creating a future as rewarding for our team as it is for the policyholders, members, and communities we serve.


Our Culture
At Windward Risk Managers, our team is the cornerstone of delivering exceptional customer experiences. We offer a relaxed, friendly workplace with onsite, hybrid, and remote opportunities. Our team members enjoy personal and professional growth, supported by ongoing education. We are dedicated to exceptional service, innovation, and creating a rewarding, fun company culture.
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Benefits

Total compensation is a blend of benefits and pay, reflecting our commitment to offering a comprehensive package that supports the work-life balance we all seek. We continuously enhance our benefits each year to adapt to changing needs. Our total compensation package includes a 401k with employer match, paid time off, paid holidays, and discretionary bonuses for our team members. Aligning compensation with market conditions is the foundation of our strategy.
Florida Peninsula recognizes nine paid holidays each year plus we give each team member an additional floating holiday to use at their discretion.
Paid Time Off (PTO) encompasses vacation, personal, and sick time. We award a generous PTO allotment to each team member, starting with 15 days per year for the first four years, increasing to 20 days in years 5-10, and 25 days when the team member reaches 10 years of service.
We pay 100% of the medical insurance premium for individual team members and subsidize 50% of dependent premiums. These plans include PPO and HSA eligible options. Additionally, we have company-paid Short Term and Long-Term Disability, Basic Life Insurance, and Identity Theft Assistance to our team members.
Our voluntary benefits include - Dental, Vision, Voluntary Life and ADD Insurance (with dependent and spouse coverage options), Additional Long-Term Disability (if qualified), Flexible Spending Accounts, Worksite Supplemental Insurance, and Teladoc. Our voluntary benefits carrier includes a comprehensive employee assistance program to meet the diverse needs of our team members.
We have a 401(k) which matches your contribution dollar-for-dollar up to 4% of base salary with both standard and Roth contribution options. Additionally, our team members have access to a homebuying assistance program and various financial seminars.
Our company is growing and there are internal opportunities for our team members to grow along with it. We have a tuition reimbursement program, and we partner with local universities with online programs, for tuition discounts. If you are licensed or hold a designation or certification, we will support your continuing education requirements to maintain them.
We recognize our team members, and we have a system that is aligned with our culture of recognition and rewards. Team members can recognize each other and award points that accumulate to purchase items, gift cards, travel etc. In addition, we celebrate and reward our team members on their birthdays and on milestone anniversaries.
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