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.

Job postings

Why Join Windward Risk Managers?

As CEO and co-founder of Windward Risk Managers, I am excited about our future and proud of the innovative, collaborative, and creative team we have assembled. Our goal is to be the premier management partner for insurance carriers, by enhancing their operations, streamlining claims, handling and improving customer experience through expert guidance and operational excellence. The foundation of our success is based on the focus we place on our team members, customers, and communities.


Windward Risk Managers is poised for growth in the coming years. Our conservative approach combined with best-in-class usage of data and analytics is what drives our decisions. Risk is inherent in our industry, but how we use the information available to us to mitigate that risk is critical to our success.


Engaged and happy team members are the foundation of our success. So come, join our team and be part of a successful, growing organization that is a leader in the insurance industry.

Paul M. Adkins
Chairman & CEO

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

All-inclusive Compensation

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.

Holidays

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

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.

Health and Wellness Benefits

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.

Additional Voluntary Benefits

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.

Financial Planning

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.

Growth and Professional Development

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.

Recognition and Rewards

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.

Contact Us

Insuring your home is one of the most important decisions you may make. Visit our carrier partner's pages to learn more about how they can meet your individual homeowners insurance needs and easily get a quote. Select one of our carrier partners below or call your agent today.