Pentland, who has been PayPal’s top lawyer for nearly seven years, entered into a separation agreement with the company Nov. 10, according to a Nov. 15 securities filing. PayPal said that as part of that deal Pentland will receive a cash payment of more than $2.5 million prior to her final separation date of July 31, 2022.
PayPal spokeswoman Amanda Miller told Bloomberg Law that Pentland will “continue to serve as a counselor and adviser supporting our ongoing activities and initiatives until mid-2022.”
Trained as a lawyer in the U.K. but perennially one of the top paid U.S. law department leaders, Pentland had previously been legal chief at Nokia Corp. She has also mentored other legal chiefs, such as Wanjiku Walcott, a former PayPal general counsel who is now the top lawyer at Discover Financial Services Inc.
In a lengthy Tuesday post to her LinkedIn profile, Pentland cited a desire to “seek renewal” after working in her “dream job.”
“None of us are maximizing our potential if we continue in the same role forever,” she wrote. “Renewal for you and your teams should be an open discussion and not hidden in the shadows. My last seven years have been exhilarating and non-stop.”
PayPal announced in late October that it would not pursue a potential $45 billion acquisition of Pinterest Inc., a social media company that saw one of its top lawyers leave last month. PayPal earlier this month reached a separate deal with Amazon.com Inc. to let its customers use its Venmo payment service.
Pentland said Bimal Patel will take over leadership of PayPal’s legal group on Jan. 1. Patel is a former head of the financial advisory and regulation practice at O’Melveny & Myers who worked in the Treasury Department during the Trump administration.
Pentland hired Patel in January to be her successor as head of the company’s legal function, she said. Martin confirmed the promotion to general counsel of Patel, who once testified about his humble origins before the Senate Banking Committee.
Securities filings show that Pentland has sold off nearly $21.6 million in PayPal stock so far this year. She currently owns more than $12.6 million in stock for the San Jose, Calif.-based company, per Bloomberg data.
PayPal paid Pentland nearly $10.1 million in total compensation during 2020, according to the company’s most recent proxy statement, down from the almost $11.2 million in remuneration she received the year prior.
Holland & Knight, Kutak Rock, and Orrick, Herrington & Sutcliffe have collectively handled nearly 30% of PayPal’s U.S. federal litigation work within the last five years, according to Bloomberg Law data. Douglas Peters, a former litigation partner at Kutak Rock, joined PayPal almost a year ago as senior legal counsel for regulatory.
White & Case advised PayPal in September on its $2.7 billion acquisition of Japanese startup payments platform Paidy Inc.