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Matt MacInnis: commitment

28 Dec 2025 Lenny's Podcast 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

“Even the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me, but it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better.”

— Matt MacInnis

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Speaker
Matt MacInnis
Attribution
Verified speaker
Claim type
commitment
Recorded
28 Dec 2025
Publisher
Lenny's Podcast

Transcript context

…To close out this thread of intensity and adding energy to everything, something I've heard about you is you're big on escalating. You're a big fan of escalating issues, and also you always tell people to never not give you negative feedback, to always share feedback to not hide anything. Tell me about those two. Fundamentally, the most selfish thing you can do is withhold feedback from someone. Who are you optimizing for when you do that? What are you optimizing for 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. It's the most selfish thing you could possibly do, is withhold feedback that would otherwise be useful to someone because you don't want to be uncomfortable. Well, that's not how high performance teams operate. So I demand feedback, and I give it, and it doesn't mean that when I give feedback, it's not open to being questioned or discussed. I mean, of course it is, but when I observe something, I try to say it. That's the feedback topic. The part of this that has been interesting to me is that people withhold, escalate, the customers withhold. Customers don't want to escalate to me as an executive. Even the founders in whose businesses I've invested who use Rippling are reluctant to hit me up when something goes wrong because they don't want to bother me, but it's literally my job, literally my job to find things, problems, and make them better, and by virtue of making those specific things better, to iterate on the processes so that the system that builds the system can get better. There's no greater gift to me as a product executive than receiving an escalation from a customer. We have an escalations team at Rippling, which sounds weird, but it's people who are just particularly skilled at pistol whipping other people in the company to get to real root causes, real root causes. Not like throw away the word root cause, like, "Oh, we fixed the data error and shut the ticket down." No, you went and you found the software that created the data error, and then you found the system that created the software that created the data error, and you solved all of that back to the top. Escalation seems extremely good at that at Rippling. So we have sort of a dedicated little team that does this for us. Escalations are a gift, and it's like, if you're a listener right now on this podcast and you are a Rippling customer and you have shit that you think we should know, the fact that I might already know it is not a reason for you to withhold the gift of your feedback. So it's an attitude that I take to this every day. I've got a little cue of some stuff that I've... Minor things that are from the last couple of days from people who had some knits and issues that I'm just like, I've got them queued up on my to do list today and I'm going to take them to the product teams directly and be like, "I'd like to understand what happened here." Not in a negative way. I just think we'll all get better if we study this one, and so yeah, escalations are a gift, feedback like that is a gift, and nobody is ever inconveniencing me when they do it. For people that are listening to this and feeling like, "Man, this is so stressful and intense and just like, I don't know if I want to work this way," give them a sense of just how successful Rippling is. I think a lot of people may not even have heard of Rippling. A lot of people are like, "Yeah, it's doing great." What are some things you can share that are public or not public that give people a sense of just how massive this business has become?…

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