Players Health, the Woj-Touted Insurance Firm, Feels Growing Pains
Players Health, the sports-focused insurance broker and software-as-a-service company, added another plume to its cap last week, announcing that Adrian Wojnarowski—the former ESPN NBA insider turned St. Bonaventure basketball GM—had joined as a brand ambassador.
According to reports, the Woj tie-in is part of a broader insurance partnership between Players Health and the Bonnies program. The move comes just four months after the company closed a $60 million funding round, which brought its total investment into the nine figures.
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In December, founder and CEO Tyrre Burks told Sportico the company had sold $80 million in premiums across 15,000 policies in 2024 alone, covering more than 5 million athletes.
A former college football player at Winona State in Minnesota, Burks has framed Players Health's growth as a personal mission to 'create the safest and most accessible environments for athletes to play the sports they love'—the company's official tagline.
Since launching in 2015, Players Health has built its foundation in the amateur sports market, securing partnerships with US Youth Soccer, USA Cheer and USA Boxing.
In March 2024, Players Health announced a $28 million funding round led by Mastry Ventures—co-founded by former NBA star Andre Iguodala—and global specialty insurer SiriusPoint.
Around the same time, the company commenced an aggressive play for the college sports insurance market, introducing a novel contract protection product for NIL collectives while also trying to get into the critical injury coverage niche.
As Sportico previously reported, this space has long been defined by volatility and controversy, with a boom-and-bust cycle in loss-of-value coverage and a trail of legal battles over disputed policies.
Entering the scene, Players Health has asserted itself as a trustworthy alternative in a market plagued by broken promises and unmet expectations.
'What sets Players Health apart is that they are an insurance technology company built by athletes, for athletes,' said a company spokesperson.
Even before enlisting Wojnarowski, Burks had garnered glowing media recognition. In 2022, the Minneapolis/St. Paul Business Journal named him one of the Twin Cities' 'Most Admired CEOs,' and Silver Waves Media included him among the '70 Most Impactful People in the NIL Space.'
Despite these accolades, Players Health advance has come with some yellow flags:
A review of public records by Sportico finds that, since 2021, Burks or Players Health has faced at least nine regulatory actions by state insurance commissioners in seven different states, primarily stemming from untimely filings and disclosure failures. These include:
March 2021: Penalized by the Kentucky Department of Insurance for failing to file surplus lines taxes on time.
July 2021: Entered a consent agreement with the Kansas Insurance Commissioner after repeatedly missing deadlines to file an excess lines report and remit taxes. Burks agreed to pay a $100 fine.
November 2021: Issued a consent order by the Washington State Tax Commissioner for failing to disclose prior regulatory actions taken in other states.
March 2022: Paid a penalty in Louisiana for failing to disclose out-of-state regulatory actions.
March 2022: Had a license application denied in Kansas due to incomplete disclosure of required information.
October 2022: Signed an agreed entry with the Indiana Department of Insurance and paid a $1,500 fine for failing to disclose administrative actions.
November 2022: Fined $500 by the Wisconsin Office of the Commissioner of Insurance for nondisclosure of previous administrative actions.
April 2024: Fined $2,500 by the New York State Department of Financial Services after admitting to nondisclosure of multiple prior regulatory actions.
July 2024: Ordered to pay a $2,000 fine by Wisconsin for failing to provide timely notice of administrative actions.
Through a spokesperson, Players Health attributed the aforementioned to 'procedural oversights that were promptly identified and corrected.'
'Since then, Players Health has implemented improved compliance protocols and engaged third-party licensing experts to ensure adherence with all state-level requirements going forward,' the spokesperson added. 'We remain fully cooperative with all regulatory bodies, and all licenses are in good standing.'
Players Health operates as both an insurance broker and a managing general agent—an independent entity that contracts with insurers to solicit, negotiate and execute insurance contracts on their behalf.
Burks founded the company in 2015 after a series of career-ending injuries cut short his brief pro career in the Canadian Football League. Initially, he raised $1.31 million in financing through convertible notes, drawing investments primarily from VC firms and individuals in his hometown of Chicago. In March 2018, the company launched an equity crowdfunding campaign seeking up to $106,699—funds it said were needed to cover two months of operating expenses while working to close a Series A round.
'Youth sports organizations are experiencing a significant increase in the liability for the failure to properly manage injuries, and protect athletes from staff misconduct and abuse,' the company said in in its offering statement filed with the Securities and Exchange Commission. 'Players Health solves the problem for sports organizations and insurers.'
Operating under the legal name Ao1 Solutions Inc., Players Health described its model as offering a free risk management SaaS platform to youth sports organizations, then using the data it collects to underwrite insurance and develop competitively priced products.
In addition to founder Burks, the company's early leadership team featured a mix of professionals with athletic backgrounds. Chris Pesigan, a CPA and former rugby player at Notre Dame, served as COO. Kari Moxness, a former University of Arizona volleyball player, led client education and performance. Dylan Wong, who played soccer at Macalester College, directed customer acquisition. Rounding out the team was general counsel Otis Grigsby, a former NFL player who played college football at the University of Kentucky.
The company's initial crowdfunding campaign closed in February 2019 without reaching its goal. However, by July of that year, it secured $2 million in fresh capital under a newly restructured parent entity, Ao1 Holdings Inc.
With fresh capital in place, the company began adding to its leadership team—a process that brought two key hires as well as legal complications.
In March 2021, Players Health appointed Jayson DeMarco as head of underwriting. He had previously been director of sports and wellness at NSM Insurance Group, which later sued both DeMarco and Players Health, alleging violations of confidentiality and non-solicitation clauses from his prior role. DeMarco and the company denied any wrongdoing, and the dispute was settled in late 2023 under undisclosed terms. DeMarco now serves as the company's vice president of underwriting.
Citing company policy, a Players Health spokesperson declined to comment on the litigation or its resolution.
Soon after DeMarco's hiring, the company named Naveen Anand as group president of insurance. Anand had recently stepped down as CEO of Hallmark Financial Services amid a class action securities fraud lawsuit filed by investors following financial troubles that led to Hallmark's eventual delisting from Nasdaq. That lawsuit was ultimately dismissed. Anand left Players Health by mid-2023 to become president of Cirrata Group, the insurance division of Ambac Financial Group, but maintained his Players Health board of directors seat until this year.
A Players Health spokesperson credited Anand for 'informing the company's growth strategy during an important period of scale.' Anand's role was not backfilled, the spokesperson added, 'as the company's structure and leadership model evolved.'
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