Bloomberg Law
March 29, 2023, 9:30 AM

WeWork’s Former Top Lawyer Picks Up Legal Chief Job at DailyPay

Brian Baxter
Brian Baxter

Former WeWork Inc. legal and compliance chief Jared DeMatteis has landed a top post at DailyPay Inc., an on-demand payroll services startup.

DeMatteis, who stepped down last month from WeWork, is DailyPay’s first chief legal and strategy officer, the company said Tuesday. He oversees DailyPay’s legal, compliance, regulatory, policy, and corporate development functions.

DailyPay is one of several new third-party pay providers that have gained popularity and faced regulatory scrutiny in recent years. DailyPay turned down a reported $2 billion takeover bid last year by Chime Financial Inc., a fellow financial technology company.

DeMatteis spent eight years at WeWork after working for Cravath, Swaine & Moore and Wilmer Cutler Pickering Hale and Dorr. He became WeWork’s top lawyer in 2021 after the exit of former legal chief Jennifer Berrent, who earlier this year became of counsel at corporate boutique Buhler Duggal & Henry.

DeMatteis received more than $4.6 million in total compensation during fiscal 2021, WeWork disclosed in its most recent proxy statement. His pay package at the co-working company included $624,000 in base salary, $1.9 million in stock and options awards, and a nearly $2.1 million bonus.

WeWork will pay DeMatteis $534,000 this year in lieu of his 2022 annual cash bonus as part of a transition services agreement, according to a securities filing last month by the New York-based company. WeWork promoted Pamela Swidler, a former head of Americas and international legal, to succeed him.

The real estate outfit announced a major restructuring this month with its former owner, SoftBank Group Corp., to raise capital and cut about $1.5 billion in debt. WeWork went public in 2021 by combining with a special purpose acquisition company advised by Cooley.

DailyPay Moves

New York-based DailyPay has been busy in recent years building out its legal and compliance team, hiring Vladimir Kleyman from Sotheby’s Financial Services Inc. to be its first-ever general counsel in 2020.

The following year, DailyPay recruited another former Sotheby’s lawyer, Jane Levine, to serve as its chief compliance officer.

A spokeswoman for DailyPay confirmed that Kleyman and Levine will now report to DeMatteis in his new role and that the company’s primary outside legal advisers are Cooley and Goodwin Procter.

DailyPay also confirmed its promotion this month of Ryan Naples, a lawyer whom the company initially hired in 2021, to be its director of public policy. Naples was previously a senior manager for public policy at Lyft Inc.

Matthew Kopko, a former Cooley associate who had been DailyPay’s vice president of public policy, is now an adviser to the company after he took a new job in January at Strive Asset Management LLC.

To contact the reporter on this story: Brian Baxter in New York at

To contact the editors responsible for this story: Chris Opfer at; John Hughes at

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