Enterprise IT Management Software
Rippling is an all-in-one HR and IT platform founded in 2016 by Parker Conrad (CEO) and Prasanna Sankar (Co-founder, Board Member). The company was built on the thesis that the market needed a unified operating system to run a company, covering payroll, insurance, HR, and IT provisioning, with Conrad and Sankar drawing directly on their experience at Zenefits to map out a multi-year product roadmap from day one.
As of the March 2019 interview, Rippling had approximately 2,000 paying customers, net revenue retention that had reached 300 percent at the time of its Series A, and had raised a total of roughly 65 million dollars, including a 45 million dollar round led by Kleiner Perkins in early 2018. Sankar indicated that 36 million dollars in ARR was not far away. The company has since grown substantially, reaching 1 billion dollars in revenue by 2026, with total funding of 2.4 billion dollars across 10 rounds and a latest valuation of 16.8 billion dollars as of 2025.
The single most striking strategic fact from the early interview is that Rippling spent 10 million dollars and 18 months building its MVP before generating its first dollar of revenue, a deliberate bet that only a broad, fully built product could capture the winner-take-all dynamics Sankar and Conrad had observed firsthand at Zenefits.
