“I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey

(instrumental music) It is really important to me that we feel that we've deliberately understaffed every project at the company. If you overstaff, you get politics, you get people working on things that are further down the priority list than necessary. That is poison. It's wasteful, it slows you down, it creates cruft.

You've been a longtime COO at Rippling. Recently, you moved into CPO, chief product officer, at Rippling. Something you talk a lot about is that extraordinary results require extraordinary efforts.

If you want to be in the 99th percentile in terms of outcomes, it's gonna be really difficult. You gotta sort of remind people that if they ever find themselves in the comfort zone at work, they are definitely making a mistake. It's supposed to be really fricking exhausting.

You're a big fan of escalating issues.

Fundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable, well, you're optimizing for your own comfort. And it's fundamentally selfish.

So many people have teams that are not functioning incredibly well.

Teams will always optimize for local comfort over company outcomes. The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop-off in intensity. That is fucking dangerous. As an executive, as a leader, your job is to preserve that intensity at its highest possible level.

You've had a couple really interesting experiences with your own startup.

We talk in Silicon Valley about never quit, but that is complete, absolute venture capital bullshit.

Today, my guest is Matt McInnis, chief product officer and formerly longtime chief operating officer at Rippling. If you don't know much about Rippling, it's a massively successful business, last valued at over $16 billion. They have over 5,000 employees, and Matt has been instrumental to that success. He's also got a really rare combination of brutal honesty, a ton of experience building a very complex and very successful business, and being able to clearly articulate what he has learned really well. Matt shared a lot of insights and advice that I've not heard anyone else on this podcast share, and I left this conversation feeling that every leader needs to hear his advice. A huge thank you to Albert Skreisand and Sunil Rahman for suggesting topics and questions for this conversation. If you enjoyed this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get a year free of 19 incredible products, an entire year of Lovable, Replit, Bolt, Gamma, Enada, Linear, Devin, Posthog, Superhuman, Descript, Whisperful, Perplexity, Warp, Granola, Magic Patterns, Raycast, ChatBRD, Mobbin, and Stripe Atlas. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Matt McInnis after a short word from our sponsors.