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Rippling announced a $250 million Series C Round of venture capital at a $6.5 billion valuation for its core HR automation suite targeting the middle market. This brings its total raised to $450 million. Sequoia led the round.

Do you remember Parker Conrad? Probably not, but you might remember the scandal he’s famous for. He’s the original founder of Zenefits that was ousted over big regulatory problems along with a $500K settlement to the SEC over charges alleging that he misled investors in the process. Zenefits aim was to “disintermediate” the health insurance brokerage industry by giving away free core HR software for the right to be a small employer’s insurance broker, which would give Zenefits perpetual commissions and fees.  It sounded too good to be true. And it was. Along the way, he got into a kerfuffle with ADP over the handling of shared customer data and account log-ins which got its own share of headlines. During Parker’s time at Zenefits it just seemed like playing it fast and loose with employee data was the model.

It’s clear that when Conrad launches a startup, he’s not satisfied with disruption or transformation that helps a function get to the next place in their evolution. He likes to blow things up. Exciting, but what he blew up at Zenefits was Zenefits.

Now Rippling has caught the eye of top Silicon Valley investors, and on the surface I can see why. Starting a few years ago automating the onboarding process, Rippling manages employee data for most of the key transitions in the employee experience. The few small businesses I’ve spoken to that are using Rippling are not unhappy. I have a hard time thinking this one ends well, given the sensitivity of employee data and the Rippling CEO’s history playing fast and loose with it. Let’s hope for those customers using it, that it does.

$13.7  billion was invested globally in work tech through Q3 2021 across 299 deals. WorkTech Market Insiders can access insights and analysis of all of the deals in our Q3 report with a free membership.

Source: Parker Conrad’s Rippling is now valued at $6.5 billion — more than Zenefits at its peak – TechCrunch

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