Rippling and Parker Conrad

analysisRippling was co-founded in April 2016 by Parker Conrad as chief executive and Prasanna Sankar as chief technology officer, shortly after Conrad left Zenefits, where Sankar had been director of engineering; Sankar left Rippling in 2020. It raised $250 million in May 2022 at an estimated valuation of $11.25 billion and $450 million in May 2025 at $16.8 billion, from investors including Elad Gil, Goldman Sachs Alternatives and Y Combinator, and launched an international payroll product in 2022. The business news outlet estimates Conrad's stake at about 20% and Sankar's at about 9%, though Sankar told the business news outlet he had divested his shares; these are estimates, and an earlier figure cited by an online encyclopedia put Conrad's stake at 22% in 2022. ^{1 2 3 4}

analysisConrad resigned as chief executive and director of Zenefits on 8 February 2016 after it emerged that the company had used unlicensed brokers to sell health insurance. According to an online encyclopedia, citing a news agency, he agreed in October 2017, without admitting or denying wrongdoing, to pay a fine to settle SEC charges of misleading investors about the company's compliance; the SEC order is not retained. Conrad has alleged, as the same entry reports, that Andreessen Horowitz and David Sacks, his successor at Zenefits, waged a proxy war in the media to ruin his image. ¹