
Nationwide
The full economics
of the case.
Data-Driven Economic Strategies for Optimal Recovery.
Proprietary quoting, independent economic analysis, and more than two decades of catastrophic-case experience—built for trial lawyers who expect more than a rate sheet.
The practice$1B+
Structured settlement premium placed
15,000
Unique cases consulted
50M
Proprietary settlement data points
50+
States, Canada & the U.S. Virgin Islands
The Winsom difference
Not all structures are created equal.
Winsom was founded to overcome the shortcomings of traditional settlement-planning firms. Our consultants use proprietary quoting to capture the arbitrage in the life market and years in catastrophic cases to change how counsel approaches the negotiation itself.
Largest payouts
Proprietary quoting techniques capture the arbitrage that exists between life markets—so the structure pays more, not just sooner.
Highest-rated companies
We place structured settlements with the highest-rated life insurance companies across the market, allowing us to compare options and build the best fit for each case.
Comprehensive counsel
From present-value analysis to MSA funding and fee deferrals, one specialist practice covers the full economics of the case.

Independent counsel · Not a sales floor
Services
One practice. Every economic dimension of the recovery.
On structured settlements
“Anyone settling a personal injury claim should seriously consider a structured settlement as part of their plan for financial recovery. Structured settlements can stretch settlement funds by providing tax-free payments for lost income, medical bills or other future needs, which delivers tremendous long-term security for injured people and their families.”

How we work
From inquiry to placement, without theatre.
01
Case inquiry
Send the facts—or call from mediation. There is no cost to involve us on a structured settlement.
02
Valuation
We model present value, medicals, wage loss, and any MSA so the number in the room is the right one.
03
Market quotes
Proprietary quoting across the life market captures pricing the other side did not know was available.
04
Placement
Documents, funding, and carrier selection close cleanly—so the recovery is protected for the life of the plan.

The founder
Josh Pettingill
Founder & Chief Settlement Officer
Consulted on more than 15,000 unique cases. Immediate past Chair of the Liability MSP Advisory Committee for the National Medicare Secondary Payer Network. A frequent expert witness, and the person who still takes the call from mediation.
Meet the practiceCounsel
What trial lawyers say.
“I never enter settlement negotiations without Josh Pettingill by my side. His expertise is instrumental for helping to resolve cases in a timely manner for maximum value and takes a lot of stress off my plate.”
Lou P.
Trial Lawyer
“Josh does an excellent job of both presenting and defending on cross examination economic damages for a jury or a settlement package for catastrophic tort claims.”
Robert R.
Trial Lawyer
From the table
Not satisfied with the other side’s expert? Call from mediation.
Never rely on the opposing structured-settlement proposal. We quote the market as it actually is—and we will be on the phone while the conference is still in session.