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Rippling's Parker Conrad says founders should 'go to the deep end' to run their companies

TechBrunchBy TechBrunchAugust 18, 20243 Mins Read
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HR startup Rippling has grown to over 3,200 employees and a $13.5 billion valuation. Despite its size, the company's founder and CEO, Parker Conrad, still approves every expense report over $10 and handles routine HR tasks like payroll — because he needs to use his company's product on a daily basis to do so.

“One of the things I love about this company is that I'm the main user of Rippling,” he said on a recent episode of TechCrunch's Found podcast. In addition to payroll and expense approvals, he uses the product to manage benefits and set HR policies, all the way down to the device management system. “I think it's a really great feedback loop, because if something doesn't work or is hard to use, it gets fixed right away because we use it every day.”

Of course, Konrad's experience with the platform may not be exactly the same as his customers', because he knows Rippling's underlying mechanics better than your average HR VP, who didn't invent the product, but he says that using Rippling directly in this way allows him to provide specific feedback to his team about how the product should work.

“We often have a backlog of administrative tasks that result in Slack notifications going out to individual product teams or engineering teams saying, 'Hey, this didn't work quite right, or this was slower than it needed to be, or the experience wasn't clear,'” Conrad says. “That's what drives a lot of our iterations on the product side.”

This is just one area of ​​leadership where Conrad takes a contrarian approach — he also said he doesn't believe in top-down management, where managers manage other managers.

“The only way I've ever been able to solve problems is by being hands-on,” Conrad said. “If something's wrong with sales, I need to look at the last 20 sales calls and see what's going on with the salespeople on my team and the interactions with the customer and what's not working.”

Similarly, if he notices a problem elsewhere, such as with customer support, he says he will look through the “last 50” support calls and “act as a support rep myself” for a few days.

He calls this approach “anecdotal,” or collecting anecdotal data, and anecdotes are much more helpful in helping a CEO understand the problem than looking at a dashboard of data about how the company is performing in a particular area.

It's a very different style from founders who believe in willpower or demanding results, similar to how Amazon's Jeff Bezos kept a public email address to sift through customer feedback and complaints. But rather than going “on the ground” to put himself in employees' shoes like a “masked boss,” Bezos would forward such complaints to managers and ask them to write detailed analytical papers, Bezos told CNBC in 2020.

Konrad also doesn't believe in the idea of ​​founders identifying what they're weak at and then hiring someone better suited for that role. He called that approach “absurd” and said founders should learn to master the things they're not good at.

“Find something you hate about your company and run towards it, embrace it, really face it and focus on it, because that's probably what's going to kill you,” Conrad said. “It's probably something you're avoiding because it's uncomfortable to focus on. I've certainly seen that with myself, and you should really spend all your time on the things you hate.”



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