We are a full-service insurance supplement and estimating company. Since 2015, we have been helping roofing and restoration companies navigate the insurance supplement process from start to finish. As restoration specialists, we know how to navigate the insurance ecosystem compliantly and efficiently.
Our Team
Mike Weckerle
President
Mike has spent a decade helping restoration contractors maximize profits and improve cash flow through accurate and timely estimates and supplements. As President of Contractor Supplement Solutions, he leads a team of 20 highly motivated professionals dedicated to providing personalized customer service and backend support to restoration contractors nationwide.
Before joining Contractor Supplement Solutions, Mike served as Sales Manager at JA Edwards of America, a roofing contractor based in Orlando, Florida. He helped build a sales team that transformed the company from a local startup to a multimillion-dollar statewide entity – giving him firsthand insight into the challenges and opportunities that contractors face at every stage of growth.
Mike is a Winter Park, Florida, native and attended Rollins College, where he earned a bachelor’s degree in economics. Outside the office, he is passionate about family and community. He spends his free time with his wife and two daughters and serves as the Pitching Coach for the Winter Park High School baseball team.
Whitney
Senior Account Manager
Whitney is an experienced Senior Account Manager with a background that blends client relations and commercial/residential construction. She currently leads team operations at CSS, where she manages client accounts, keeps workflows running smoothly, and helps ensure projects stay on track and on schedule.
Before that, she worked as a Project Engineer at Williams Company, contributing to large-scale developments like Vineland Pointe and major retail builds including Target and The Cheesecake Factory.
Whitney started her career in account management at Disposall, where she built strong client relationships and played a key role in supporting business growth through thoughtful account management.
Mateo Trinidad
Senior Account Manager
Mateo is a Senior Account Manager at CSS, where he oversees and supports contractor clients across the United States. In his role, he focuses on helping clients get full recovery on their insurance jobs by providing strategic guidance and responsive service. Prior to joining CSS, he built a strong foundation in customer service through his work in call centers, where he developed excellent communication and problem-solving skills. He brings a client-first mindset into the role, ensuring every partner receives attentive and results-driven support.
Mitch Tomlinson
Senior Account Manager
Mitch is a Senior Account Manager at CSS, helping provide compliant customer service to contractors in all 50 states. He worked as a project manager for a home builder for a few years before entering the storm damage restoration industry in 2016, specializing in residential and commercial roofing projects. He is committed to delivering a personalized experience for every contractor, clearly communicating throughout the entire supplement process.
