The Exchanges

Q for that 25 person company that's building some SaaS product. They're hiring their first VP of sales. You're obviously highly competent. You've done similar things. What is the bad thing that would happen or the suboptimal thing if you did what most people do and tried to, you know, help them with their specific situation instead of kind of giving them these movie clips of your kind of earned experience?

A Hazard number one is that you are implicitly alleviating the Executive, the CEO, the founder of the need to think from first principles. One of the most difficult realities that I had to come to terms with as a CEO, and this in turn has made me a far more effective COO, is that I'm never going to feel comfortable with my answers. Number one, the hardest questions always bubble up onto my plate. So if there were an easy or obvious answer, it would have been done below me. And so by definition, I'm going to get all the nuclear stuff. Number two is like this sort of really high blast radius Questions are inherently ambiguous, and so I'm never going to have confidence in my decision. I could spin my wheels for days and weeks trying to come up with a better answer, but option A and option B, if I'm lucky to even have options, blow. You know, what you eventually learn is like, number one, you got to live with that discomfort, and number two, it's about how quickly you choose one and learn from it, not about whether you choose the right one. If A and B both suck, pick one and go.

AI assessment note: “you are implicitly alleviating the Executive, the CEO, the founder of the need to think”

Q You spent a decent portion of your career building a company yourself as the founder and CEO, something like 10 years, I think. You're five years into being the COO of Rippling. What has being in the COO role taught you about being a CEO that maybe you didn't know when you were actually in the seat?

A First thing I would say is that every CEO succeeds For his or her own reason. The CEO job is inherently idiosyncratic. It's specific to the market you're in. It's specific to the team you have. It's specific to the moment in time scale of your company. It's like all of these really broad variables determine what is needed of a CEO. And then the CEO shows up with his or her strengths and like plays those strengths all day, every day. And one thing that's really clear about successful CEOs is that they don't ever really worry about the downside of their strengths. Like they just go almost blindly, just like at the business, applying their instincts. And then there's a lot of downside that can come with, you know, a spike. One area where my CEO Parker spikes is like, he's very direct, does not pull any punches. He almost, you might even say lacks empathy when it comes to delivering a directive or, or difficult information to somebody. There's downside to that. You can upset people. You can stir the pot. You can create a lot of chaos, but like that doesn't matter. Like he comes in with that strength and applies it relentlessly all day. And so when I was CEO, I think I worried too much about the downsides of my strength. My strengths are a little different. I'm more of an empath. I can read the room really well. I can sort of get people to understand a difficult thing without creati…

AI assessment note: “when I was CEO, I think I worried too much about the downsides”

Q Can you talk a little bit about some of the other stuff for you in particular? When you're sitting down with someone that's kind of going on in your brain that you're trying to suss out in them?

A It's really funny to me that people think that the content of an interview is about the content of the interview. The interview is the metadata. I don't care what topic we're talking about. I'm studying the way you think. I'm studying how you communicate. I'm studying how you respond to challenges and pressure. We could be talking about cars. We could be talking about rollerblades, you know, experienced executives. A hundred percent get that. Everybody should get that though. What it means is like cut loose, just be yourself, do your thing. It doesn't matter what the topic is because the useful information for the interviewer is sort of fitting you to the, to the organization on the basis of the things around the topic. The stuff that I look for when I'm spending time with an executive, I'm really happy that I have had as much batting practice with senior people over the course of my career so far as I have, because it's given me a good intuition for whether someone is a high performer. What I've Honed over the past five, six, seven years, I think is an ability to then interpret my gut, describe my intuition in a way that's productive to helping other people make a decision or to flag concerns that can get a little bit deeper dive. Only like three or four years ago, I remember there was a, an acronym I came across on LinkedIn from someone who had tipped to this guy, but I don't…

AI assessment note: “I'm studying the way you think. I'm studying how you communicate.”

Q Hang with me. Um, so with that sort of framing, how do you think about where you want to put those people?

A I'm going to give you a concrete example of like where this specific dynamic played out at Rippling recently. So we have a lot of products. We have payroll product, benefits administration product. We have spend management product. It's hard to market all of that at once. If you have a single product In a single market, your product marketing team can go do the sort of expected thing. They can build the messaging document for what people in that market segment care about. They can tease out your one or two big differentiators. And then it's about like cranking through that over and over and over. It doesn't change that much. One of the challenges of marketing a product like Rippling is that you've got to be able to talk about the platform benefits and like why every application that runs on the Rippling platform is better than any standalone SaaS application that would run on its own. Because of the underlying data structure and this kind of thing. So the challenge is harder. When you go shopping at Ross, it is hard to find a Gucci bag. If you look into the ocean of product marketers, it's kind of like shopping at Ross. It is not a job that demands a lot of really deep first principles thought from people in the job. There's lots of really smart product marketers out there. If you do your listener or a product marketer, I'm sure you're brilliant. There's a lot Of people who are…

AI assessment note: “I'm going to give you a concrete example of like where this specific dynamic played”

Q But you often have people that are more junior with more equity. That's the nature of a startup, right? You're the ninth employee. Yes. You get layered seven times down. Yep.

A That dynamic can happen. The other dynamic that can happen kind of in the other direction is that you'll have people who are really vested in the business because they view it as a career opportunity. Kind of regardless of the equity. The reason I say this is because like me reporting to me, probably the subordinate me probably doesn't have quite the same desire to win and or fear of loss that I personally do have today. And so I sort of, I say this because like you have to acknowledge that dynamic in any organization, even the early employee who has a ton of equity, but it's been layered a few times is still going to have a little wind taken out of their sails by that very fact, even though they're, they're significant equity holders. There's just like a finite number of people in the world who have that hunger And I think the answer to that is like, absolutely. I think it's extraordinarily rare that someone just loves their work and gets out of bed in the morning and just gets fired up by it and wants to fight the good fight and dig in and push and drive. That is your A player. That's your star player. And like, you just don't, God doesn't give us too many of those to work with. When you find them, this is a whole other topic. It's like, when you find those people, man, you got to load them up with responsibility. Far in excess of what you think they would be capable of on pa…

AI assessment note: “even the early employee who has a ton of equity, but it's been layered”

Q To wrap up, I'm curious, when you think about all the spectacular people that you've had the chance to work with, is there anything that just pops to mind that's had some sort of disproportionate effect on the way that you think about Building companies now. Could you kind of crystallize the thing that they imparted on your worldview?

A I would say for me, the biggest growth, man, this is where I can really get, get into it. It's like one big growth thing for me from when I was younger to where I am today is accepting who I am. And I know that that's a really cliched, broad thing to say, but like I spent, like I was a gay kid in a tiny town in the middle of nowhere and I needed to be somebody else. I needed to be somebody else. I needed to be somewhere else. I spent my energy in my twenties trying to become the somebody else, the somewhere else that my 18 year old self wanted. And somewhere around 30 or 31, I looked back and I'm like, why the fuck am I still trying to please that 18 year old? He doesn't exist anymore. Why am I operating in his frame? I began to operate without a frame, which was, I just was in the moment trying to be who I am. Didn't like who I was and had a lot of self-doubt and Self-criticism and a lot of voices in my head telling me that I wasn't worth much unless I did this or unless I achieved that. And it was only when I let go of those things that I started to perform well because I was just free to be who I was as opposed to who I thought I was supposed to be. And what's amazing is that when you free yourself of the shackle of self-doubt and self-criticism, you become a resource to other people who are a few steps back on that journey, but you can spot it from a mile away. And one of t…

AI assessment note: “It's like one big growth thing for me from when I was younger”