Penn Entertainment announced a new corporate organizational structure, a move designed to align the company’s leadership with its strategic priorities.
Photo by Danielle Cerullo on Unsplash
In a press release, Penn said the new structure reflects a realignment of Penn’s Interactive segment, which will focus on “PENN’s digital assets in Canada and its Hollywood iCasino product in the U.S. to further leverage its core retail casino business and overall omnichannel business model.”
The language signals a narrowing of Penn’s Interactive focus toward digital casino and established international assets, rather than U.S. online sports betting expansion
Penn’s CEO and President, Jay Snowden, provided a statement on the restructuring’s objectives:
“As we turn the calendar to 2026, we are restructuring our corporate organization in order to achieve greater operational efficiencies, deepen customer engagement across channels, maximize free cash flow, and drive shareholder value.”
Executive Departures and Role Changes
The press release confirmed the departure of two senior executives and the elimination of their roles:
“Todd George, Executive Vice President, Operations, and Rich Primus, Senior Vice President, Chief Information Officer (‘CIO’), will step down, and their positions will be eliminated.”
Under the new structure, several senior vice presidents will retain operational oversight with adjusted reporting lines:
- Rafael Verde, Aaron Rosenthal, and Justin Carter will continue to oversee regional retail operations. Verde and Rosenthal will report to Snowden, and Carter will report to Verde.
- Jennifer Weissman, Chief Marketing Officer, will report to Snowden and focus on “maximizing omnichannel results,” working with Penn’s technology leadership.
Penn added that Chief Technology Officer and Head of Interactive Aaron LaBerge will assume responsibility for enterprise IT functions in addition to his current duties.
Furthermore, the company has initiated a search for a digital Chief Operating Officer. The role will oversee the day-to-day operations of the Interactive segment, reporting directly to LaBerge.
The release also stated that the company will provide an update on anticipated annualized cost savings and improved free cash flow generation when it reports its fourth-quarter 2025 financial results in February 2026.
The organizational changes are effective immediately, according to the release.
Industry Context
Tie-In With ESPN Bet Strategy
The leadership restructuring arrived two months after the company and ESPN agreed to terminate its U.S. online sports betting agreement for ESPN Bet. After the termination, Penn rebranded its sports betting app to theScore Bet, which launched on December 1.
While the organizational press release does not reference the ESPN Bet exit, the change highlights the company’s ongoing realignment of its interactive and digital leadership in the wake of that strategic shift.
The ESPN exit occurred two years into a 10-year, $1.5 billion licensing agreement. The ESPN Bet partnership followed Penn’s decision to sever ties with Barstool Sports. The company had spent approximately $500 million on Barstool, only to sell it to its founder, Dave Portnoy, for $1.
Before Barstool, the company acquired Score Media & Gaming, the parent company of theScore, in 2021 for roughly $2 billion. In 2022, it shut down theScore Bet to focus on Barstool.
Overall, Penn has invested roughly $4 billion across Barstool Sports, theScore, and ESPN Bet over the past five years. However, these investments have yet to translate into sustained market share gains in the U.S. sports betting market.
Broader Governance and Investor Pressure
Penn’s Interactive Division and its performance relative to initial expectations have been a primary focus of broader investor scrutiny from activist shareholder HG Vora. The shareholder has pushed for changes in board structure and strategic execution.
HG Vora, whose nominees were elected to Penn’s board in 2025, has criticized aspects of the company’s digital strategy and governance. The shareholder also filed a lawsuit against Penn. It alleges that Penn breached its fiduciary duties by reducing the number of seats up for election from three to two.
Penn’s press release does not cite this investor pressure or specify that the restructuring is a response to external shareholder demands. Still, the governance environment remains a backdrop to the company’s strategic reassessment.
What’s Next
The company stated that the leadership changes are expected to support operational optimization and omnichannel execution, and will be discussed further during its upcoming Q4 2025 earnings call, scheduled for February 2026.
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