About us

Meet our Founder

WHO WE ARE

Josh Pettingill is the Founder and Chief Settlement Officer of Winsom Settlements. He works with clients throughout the country to resolve general liability, personal injury, medical malpractice, and worker’s compensation cases. Prior to starting Winsom, Mr. Pettingill was Co-Founder and Principal of a national settlement planning firm dedicated to assisting personal injury stakeholders. Before that, he spent ten years assisting injury victims as a Settlement Consultant and Principal for one of the largest plaintiff-based structured settlement companies in the country. He was consulted on over 15,000 cases with unique fact patterns. Mr. Pettingill also frequently testifies as an expert witness on the economic value of cases. He is the immediate past Chair of the Liability MSP Advisory Committee for the National Medicare Secondary Payer Network.

Mr. Pettingill is a frequent lecturer at national trial lawyer and industry trade associations. He has presented to the Florida Justice Association, American Association of Justice, Academy of Economic and Financial Experts, Worker Injury Law & Advocacy Group, Maryland Association for Justice, Virginia Trial Lawyers Association, Florida Workers Advocates, Academy of Special Needs Planners, National Alliance of Medicare Set-Aside Professionals, US Virgin Islands Bar, and many other organizations. He has authored over 100 articles and taught over 1000 hours of CLE’s on complex settlement planning issues.

$1 Billion

Structured Settlement Premium Placed

15,000

Unique Cases Consulted

50 Million

Proprietary Settlement Data Points

11

Books Read This Year

How can we help you?

SERVICES

Settlement Planning

Not all settlement plans are created equal. We create a customized plan to enhance your life, protect your financial security, and ensure the needs of you and your family are safeguarded.

Case Valuations

With our unique expertise and specialized skills, we can help you prove damages and accurately calculate the value of any personal injury or workers' compensation case.

National Coverage

 Winsom provides services in all 50 states, Canada and the US Virgin Islands. Whether you are in a big city or on a remote island, we have  you covered.