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[upbeat music] Hey everyone, welcome back to the show. I'm Scott Inmenta, founder of the Chief of Staff Network, and today I'm really excited to share a conversation I had with Brian Silverman.

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Brian is the COO at Suzy, which is a market research platform that helps companies learn from their customers.

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Brian incredibly has been at Suzy for almost eleven years, and he's basically reinvented his career multiple times without ever leaving.

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He started as an SDR, moved into enterprise sales, then became a chief of staff when the company was going through a major pivot.

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From there, he went into biz dev, then product, then a GM-style role, strategy and ops, and now finally as COO. What I loved about this conversation is Brian's really honest about the messy parts.

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He talks about being a first-time manager during COVID, about learning to delegate when his instinct was to do everything himself, and about what it actually means when people say you're involved in everything but in charge of nothing.

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So whether you're a chief of staff role right now or wondering what comes next, or you're already in a leadership position trying to figure out how to spend your time differently, I think you're gonna get a lot out of this one.

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Let's get right into it. Brian, welcome to the podcast. Thank you. Really excited to be here. It's nice to, uh, have you here. It's also nice to see you again. It's been kind of a long time.

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We haven't seen each other in person in a long time. Yeah, for sure, and I know it's been a long time since we got started together with Chief of Staff Network, so it's been fun.

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I mean, you are one of the first members of the community, so for that I am grateful.

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That also means you have a long story to tell and an awesome history just kinda looking back at your career as a chief of staff and in other roles, and so I'm excited to dig into that with you today.

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Looking forward to it. Your path at Suzy, and we'll, we'll talk a little bit about what Suzy is just to give the audience a background, but it was quite unconventional, I think to say the least.

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You started out, from what I understand, as a more kind of enterprise account executive role. You ultimately went into biz dev for like a very small part of your time there.

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You ended up in a chief of staff role, obviously, which we'll dig into as well, and now you're serving as COO.

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For the listeners that don't know your story by just glancing at your LinkedIn, give us the quick version of kinda where you ended up today. Sure. So before I joined, our company used to be called Crowdtap.

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Before I joined Crowdtap back in twenty fifteen, I was a founder, started a company with my brother that we did for four or five years. We raised some angel funding, hired some people.

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We loved doing that together and doing entrepreneurial journey, but we weren't really able to get past that initial funding stage and, and get to that next level.

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And so, you know, I wanted to find something that was gonna scale. I wanted-- didn't wanna join a ten-person company and didn't wanna join a thousand-plus person company.

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And so I found my way to what is now Suzy actually as a SDR, so entry-level sales role.

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Was there for about a year, year and a half, and we were probably about fifty to a hundred employees at the time, and I kinda moved my way through the sales organization, and we went through this big pivot.

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And at that time, probably a year and a half, two years in, a lot of people who are two years into places are like, "Eh, like maybe I'll move on to a new thing," and we were seeing some major change, and I had a bunch of people leaving at the org, and you know, it was back of my mind too.

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But I got offered this opportunity to be chief of staff for my CEO. You know, I was recommended by my boss at the time, who's head of sales, and I had no idea what a chief of staff was.

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And I asked around to a couple people, "Would you raise your hand for that position?" My CEO came to me and asked like, "Hey, I'm, I'm looking, you know, I need somebody to be a right hand.

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Like, do you wanna be my chief of staff?" And so I asked a couple people in my life. I asked one person, and they're like, "Oh, that's basically the COO. That's awesome."

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And then I asked another person, and they're like, "Oh, that's an exec assistant. I don't think you should really take that role."

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And it turns out they were both right, depending on the, the minute or the hour that we were operating in and, and everything in between, right? But I was so happy I did it. You know, I, I took a leap of faith into it.

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I was good in sales. I like sales, but it wasn't gonna be my future forever. I wanted to see how a company grew, and this is such an amazing front door into that.

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And so I joined that chief of staff role, did that for about a year and a half, two years.

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As you mentioned, I had a stint in, in sort of biz dev and partnerships, and then over the last five, six years, I've moved into a couple of different roles.

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One is sort of a GM-style role overseeing one of our business units, call it product and marketing. I've overseen our net new sales team in my role.

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I subsequently ended up as COO a couple years ago here, and I've kind of taken on a couple of different big projects around transformation in different parts of the team and, and now I'm overseeing product engineering team, our HR team, our IT teams, partnering really closely with our head of commercial and kind of us forming, uh, our triangle with the CEO here.

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And so I think, you know, my time as chief of staff, and we'll go into it a little bit more, but I view it as like the ultimate career accelerant for me, uh, exposing me to all parts of the business, learning new things, getting new opportunities, meeting new people.

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You know, I definitely would not be in the role I am today if I, if I hadn't taken that leap originally. That's awesome. Let's flash back to when you kinda first raised your hand for that chief of staff role.

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You mentioned, you know, you had kinda two competing colleagues sitting on one shoulder and the other saying, "Hey, look, this is gonna be an EA position, probably not what you want," or, "Hey, this is gonna be a more of a strategic COO position.

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Are you even ready to handle that kinda role?" It must have been pretty daunting decision kinda even at that point in your career to take that on. What made you raise your hand for it?

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Did you have a relationship with your CEO already that you kinda trusted what you were getting yourself into? What was the thinking there?

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I had a little bit of a relationship, but I think honestly it was my boss at the time who was head of sales, who had worked with my CEO a lot more than I had and, and said like, "Look, you wanna be a founder or CEO or, or something in the future, right?

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Like, you wanna run businesses, and so, you know, this is a great opportunity for you to get that front door."

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And I think given where we were as a company and the stage that we're at, go-to-market and distribution was like our number one priority.

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And so it was kind of an easy on-ramp, right, for me because while, yes, we had all this other stuff around investors and different ways we had to run the company and what I now know to be operating cadences and stuff like that, really it was like either we're gonna go out and get revenue or this thing's not gonna work.And so every day I was spending a lot of my day being our de facto kind of head of sales because we didn't, we didn't have a head of sales after my previous boss had left.

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I was my CEO's personal SDR, going through his Rolodex, going to find folks that we should go meet with and sell Suzy to.

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And then I was able to go with him and get on a plane and go pitch Suzy to a bunch of CMOs that he knew, right?

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And so it was this really cool, I think, transition for me from what was my role as an enterprise AE and a previous SDR to a way that I could drive high impact with seventy-five percent of my time, and then the other twenty-five percent, I got exposure to how the product was getting built or our investors and our board or, or anything like that.

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I mean, what an amazing ramp-up to get just kind of a much more holistic experience and view of the business in a moment where the business kind of needed exactly what you were doing in the AE role, but you could be obviously a lot more effective having your CEO as your right hand or vice versa.

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Yeah, definitely.

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And I think in hindsight, every company has inflection points, and product is important and sales is important, and renewals are important and all that, but at the time, it was definitely like, can we sell this thing to new enterprise customers?

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Like, is that-- that's gonna be our make or break.

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And so I think there's a lot of reasons that I, I think being in that role worked out, but I think one of those is the fact that that was kind of my background, my experience, and, and I think that was a nice way because my CEO had seen me be successful in that role, and so I was able to kinda have some relative autonomy in being able to be successful there while also taking on some of the, the new things that I might be taking on over time.

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Were there other things that emerged kind of in those first few months that were not expected?

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Was there anything that you had to kinda navigate that, you know, maybe created a little bit more tension between you and your principal or just things that you were not kinda willing to sign up for?

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I don't know about not willing to sign up for, but I think it was more so about, like, what else came with the territory of being in the role.

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And I think one of the things that definitely came with the territory was around the world of, like, leadership and management.

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I wasn't formally managing a lot of these folks, but I was the CEO in the room when he wasn't there.

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And so you're kind of in this awesome, strong position, but at the same time, you wanna figure out how you can leverage the people at your organization.

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And I think, you know, now I'm seven, eight years removed from that role and, and I have a much better concept of what it means to be a leader and a manager and ways to do that.

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But I think at the time, you know, especially as a startup that was figuring out if we were gonna get through the other side, you kind of make everything-- You're a hammer and everything's a nail, right?

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And you're just like, "Go, go, go. Go, go, go."

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And I think that was definitely something that was a huge learning, and I got, you know, a decade of learning, I feel like, in a year and being able to be in that role, which is awesome. But that was definitely there.

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And then I think, two, was as any org, like, you're starting to shift through different leaders and executives and so on, and I think being privy to those conversations, but not having previously been, and knowing exactly how to navigate those things and how do you bring in the right executives and so on.

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Again, awesome learning, but definitely hard and, and challenging to figure out exactly how to navigate those things.

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There's a phrase I've heard from other chiefs of staff, involved with everything, but in charge of nothing. It resonates immensely.

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[laughs] You know, whether or not you're managing people directly, how do you hold people accountable when, you know, they don't report to you-- directly to you?

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Did you experience that tension, that kind of dynamic early on in your chief of staff role? Is it something that you had to navigate?

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You know, for the first six months, you're in this honeymoon-style phase where you get to be involved in everything, [chuckles] and it's so cool, right?

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And going to zero one on things or helping to push big things forward or anything like that. But you pretty quickly see that you can't actually do everything and be involved in everything, right?

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Like, that's how organizations ultimately have to run.

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And so I think you end up getting overwhelmed with all the stuff you have to do, especially due to the fact that, like, I can't just put in a hundred-hour week and do it, right?

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Like, I'm not gonna go and build a product or go do our marketing campaign or go hire all the people or anything like that.

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You can have moments in time where you apply yourself towards those things, but that can't be the, the forever state unless you go and take on that role for real, right?

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Like, there's a reason that there's real roles for those types of things.

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And so I think there's definitely a tension of involved in everything, but in, in charge of, of little or in charge of nothing, depending on how folks operate, right?

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And I think that ultimately the thing that was helpful for me is, and maybe this is revisionist history in my head, but, like, being able to be as upfront as possible with the people you're working with about who is deciding what and who is involved.

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Because I always talk to my CEO now about this too, like, technically, he can make a decision on everything. [chuckles] Like, he is the ultimate decision maker, right?

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But that's not necessarily a great way to run a business.

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And so I think, you know, especially as chief of staff, when you're kind of wearing the CEO hat when they're not there, ensuring, like, clear decision rights, if you will, which feels weird when you're a startup or a small company, but just letting the head of marketing or the head of product or the head of sales or whoever you're working with know, like, "Hey, I'm here to help accelerate this thing," but you're in charge or sometimes not, right?

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Sometimes if that's the thing that you're ultimately coming in, like, "Hey, we need to ramp up our events strategy.

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I'm gonna take this on for three months, but our goal is at the end of three months that, like, we're scaling this thing out."

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And so I think making sure that when you are involved, understanding your role is really, really important.

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Is there a example of a project from your kinda chief of staff days that you're still proud of, and maybe it's something that you own directly or indirectly, which is more often the case? Yeah.

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And I think this is funny 'cause, like, it's ebbed and flowed, especially as we started going remote and all that sort of stuff.

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But I think moving us from, like, a go, go, go mode to, like, establishing a real operating cadence was something that I'm, I'm really proud of and something we're still trying to do.

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And I think what I realized is, like, I used to think that was, like, a big company thing. Big companies operate on quarterly and annual plans and so on.

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Like, our job is just to, like, build a good product and sell a lot of stuff. That's it. Go, go, go.

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And I think in hindsight, you know, as we started to figure out that, you know, we needed to collect these groups of people, make some big decisions, make some big bets, and then get the whole company behind those things, that was something that, that I'm definitely proud of because I think you realize that you work with a lot of really smart people who wanna work really hard, and if all of that energy goes towards the same couple of things, it's extremely powerful.

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But if all that energy doesn't, not only does it dilute each piece of the puzzle, but it's actually real frustrating for everybody because inherently, again, if you're head of product or head of mar- like, you're relying on each other.

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If you're building out a product strategy, a good product is necessary but not sufficient, especially for us who operate in the enterprise. And so ultimately, making sure that these things fit together is important.

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I was glad that we did some of that stuff because come March 2020, we were not a remote company, and everything went remote.

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Everything got exponentially harder.To be able to be on the same page and know the big bets and be able to communicate with everybody.

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We weren't just able to collect fifty people at the front of the office and say like, "Oh, we're going left now. Hey, we're going right. We're gonna do the blue button," right?

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Like, it just doesn't work like that anymore when you're doing remote.

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And so remote afforded us the ability to get incredible talent with so many amazing things, but it definitely made decision-making, communication about key priorities a little bit harder.

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And so I think having that operating cadence was great. And I think, look, like there's times when we've overdone it too.

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We've had too many meetings and OKRs and documentation, and we spend a lot more time planning the business than working in the business or on the business.

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And I think we've learned a lot from that about like what is a, a good version of that look like and what works for other companies and with other executive teams might not work for us.

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It's always an amazing opportunity when you're learning throughout your career and the company's kinda going through those same learning curves to a degree.

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And so as you're figuring it out, you know, the company also needs to be figuring it out.

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And so, you know, you're adding kinda new processes and new definitions and, and new ways of working together that help the company to scale, and it sounds like for you as like in a chief of staff role, thinking about the operating rhythms here, I'm sure a lot of the lessons that you learned as a chief of staff at that point are still things that you're leveraging today as COO.

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You did your chief of staff role for, remind me, around two years, right? Yes. At what point did you start thinking about what was coming next? You're growing as a leader here.

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You're getting more exposure to the company's challenges. How did you start thinking about approaching that transition? What was kinda the immediate next step for you?

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So I think what was interesting is like, I don't think that at the time I was like, "Oh, like I'm gonna do the two years and then move on."

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I think especially at the time, chief of staff was a little bit newer role, right? And it wasn't quite as established that people tend to take a couple of years and then find something and that sort of thing.

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What ended up happening was, you know, I was getting involved with this one team on the product side and this one business unit. So Suzy's a primary market research platform for all intents and purposes.

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We help customers learn from their customers who work with big Fortune five hundred companies, and one of the pieces of the platform was that we were vertically integrated.

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So we had the respondent set of people who were consumers who you go out and, and ask questions to and get answers from, and that itself was like a product. It was a consumer product and a mobile app.

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We had to do marketing and so on and so forth.

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And based on the way that Suzy was founded and this pivot out of a previous company, we fell into this awesome asset of what CrowdTap was before, and we hadn't really given it the love that I think it deserved to set us up to be able to scale with our enterprise customers and go from three to five to ten to twenty-plus million in revenue.

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And as I worked more and more with that team, I just realized there was a big opportunity to invest more and be more involved with that and ramp up our marketing and our acquisition spending, ramp up our lifecycle marketing and engagement, ramp up our product investments in a way that would allow us to functionally operate this marketplace between supply and demand with customers and consumers.

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And so as I realized this, I went to my boss at the time, I was like, "This is a place we need to start focusing.

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It's not yet falling apart, but we haven't invested enough in this place of the business in order to support our customers."

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And, you know, had some conversations, talked about what I might do, and at the end of the day, he's like, "Okay, why don't you just take it on? Like, why don't you do this?"

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And so it wasn't a conversation necessarily of like, "Hey, I feel like I'm nearing the end of my time as chief of staff. What's gonna be next?"

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necessarily, as much as it was like, "Here's a new problem to go solve for the business, and this problem is not something that you'll go take on for two months and then move on to the next thing necessarily."

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And so that's how I ultimately moved on from, "Hey, I'm gonna be a chief of staff," to the next kind of thing that I woke up and, and it was really...

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There were a lot of awesome things about it, a lot of challenging things about it, but I literally went from, as you said before, in charge of nothing and involved in everything to like that, involved in this one thing and in charge of all of it [chuckles], right?

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And like that was a very jarring experience for me because, you know, it's nice to be involved in everything.

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You know everything that's going on, you know all the people and all that sort of stuff, and then all of a sudden you wake up every day thinking just about this one thing, and there's awesome pros and difficult cons about, about that transition.

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It can be a hard transition for that reason.

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You're giving up a lot of access so that you can go deeper on one part of the business, and sometimes giving up that accessibility means a feeling of a loss of power or control or just visibility, right, and voice.

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For all the interesting stories I hear of chiefs of staff moving on to their next things, they very rarely happen because the chief of staff is necessarily forcing it, but they almost always happen because the chief of staff has raised his or her hand and said, "There's a problem over here that I wanna go solve, and I need to be more than a chief of staff to go solve that.

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Like, I really need to be in the trenches." And whether that's a leadership position or another role, that becomes kind of the way out.

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And so I'm curious, when you made your way over to the product side of the organization, brand new territory for you, what was that like for you? Was it a new discipline that you had to learn?

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Is it something that, again, you kind of carried those skills on with you? Is it just a blip in the radar of your career? It's core and fundamental for sure.

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I think it was like a really big turning point because for me, as I go back in my career, right, I was a founder, I was an entrepreneur, like I wanna run businesses, and then the way I did that and the way in, my wedge, if you will, right, was through sales, and it was through customer relationships.

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And I think for anybody out there that's listening, like sales is one of, if not the most fundamental skills that you can learn to go and do anything.

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You can go do it, go and be in product, go be in HR, whatever you want, right?

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The idea of like asking real questions and actually caring about the answer and being able to persuade people, ask for the money, ask for a job, whatever, I think is a core fundamental skill to...

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no matter what you're doing. But if I looked at the pie chart of my experience, it was like ninety percent commercial, if you will, in some capacity, right?

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And like ten percent operational, twenty percent operational, eighty percent. I knew the people in the product and the marketing side, but I didn't know really what they did all day.

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I didn't know what it took to build a product.

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I remember I had this one experience, um, at the time, you know, a, a product manager and, and I went to her and I was likeI don't really know what a software development life cycle is and what QA is and what tickets are, and can you just like walk me through, like when we say here's an idea till like now a customer is touching it, like what happens, right?

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And I remember we had a, you know, this is back in the office, and we sat in the back and, you know, I have a very distinct memory of it, and I think it was almost awesome that I had this level of naivete to go and ask the dumb questions, if you will, right?

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Because it afforded me that opportunity, but I was coming with the business strategy and the customer problem at heart.

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And so I just had to go and learn how to either leverage the best people that were on the team or go learn some of those skills.

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And, you know, I, I did a report course in consumer marketing and product and, like, you know, I did some crash courses in that that were immensely helpful and helped bring some frameworks.

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You know, I think recommend any of those things to anybody, especially as they're learning a skill, because otherwise you just get inundated with the problems of the business and the things you got to solve, and you don't actually know how to do any of it, right?

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Now, I'm overseeing our R&D team, for example, and like I, I never could have been able to do that if I didn't spend four years overseeing this business unit that was kind of part product, part marketing.

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And so I think for me, being a generalist has been really helpful and really impactful.

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And I think this is an example of where being able to come with a sales background, understanding the customer, and then from my chief of staff background, having the business needs and strategy in the back of my mind, then being able to deploy that through product and marketing was impactful.

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I think one of the most important things that you just said is that you recognized where your skills were on the commercial side, but also where some of the gaps were.

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And, you know, as we said before, A, you were willing to kind of raise your hand and, and jump into that knowing that you had to kind of ramp up the skills and being brave enough to ask for help as well, clearly, you know, kind of pushed you along.

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And obviously signing up for outside courses and, and kind of doing the work. This was also the first time I believe that you were managing people, right?

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Talk to us about that transition because now you're moving from chief of staff, leading without authority to all of a sudden having all the authority, but also all the responsibilities.

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And so what did that transition look like for you? That was really hard. [laughs] This is all around when COVID is starting, right?

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So I started overseeing the team January twenty twenty, and six weeks, eight weeks later, we were like, "Hey, we're also gonna have to do this thing remotely."

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So we're gonna go build a business, we're gonna run the business, and you're gonna start to become a manager all during COVID. It was really hard.

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I mean, I think to be honest, I went into it thinking management was just telling people what to do, and then they go and do it. [laughs] Right? Um, and that's not a, a knock on any of my managers, right?

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Like, there's so much more to management than just that experience that you see on the other side of what it actually takes to coach people, to hire people, to have difficult conversations and all those things.

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And so I think one of the things, you know, whether you're talking about learning product or learning management that I always try to do and, and hope will always persist throughout my career is just like the recognition that, sure, I think I've learned a lot and I know a lot, but like I'm constantly learning, right?

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And I think, you know, it's important to have conviction and, and believe in yourself, but at the same time, I've been here at Suzy for nearly eleven years because every day feels like I'm learning something new.

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And I think for me, that was a time where people bet on me and helped me, you know, experienced managers at the company who helped me and, and, you know, we had some management courses, especially we wanted to double down on them in a remote environment because all of a sudden you're not tapping your employee on the shoulder and saying help or anything like that, right?

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But it was really hard.

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I mean, I, I look back at some of the decisions I made or some of the ways I managed or anything like that, and often as a new manager, for me, it erred way too far on the side of, I guess I'd call it being too nice.

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We employ radical candor, and so, you know, ruinous empathy, I think, was heavy in my management style for the first few years as a result of that.

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Even COVID aside and all the difficulties and hardships everybody was going through during that time, giving hard feedback is hard.

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And until you realize that that's what great people want, it feels hard and it feels uncomfortable.

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And so I think that concept of people management, whether it was coaching, whether it was setting a vision, whether it was making decisions when there's people who are disagreeing, I could go on and on about all those things that you don't really experience until you experience it, was a difficult but I think really important transition.

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You know, I talk to a lot of people who look at people management, and they're like, "Gosh, that kind of sounds terrible." [laughs] And I'm like, "To be honest, sometimes it is," right? I'm like, "Sometimes it is."

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I often tell people, like on a day-to-day basis, it often is, but on a week-to-week or month-to-month basis, it's awesome.

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When you reflect on people who are growing, who are taking on new positions, even if they go somewhere else that's out of your company and, and you've had a part in that, I love that.

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And for other people, they wanna be an IC seller, an IC engineer or anything, and thank goodness we have those people too. There are two common factors in the glass ceiling of ch- most chief of staff roles.

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One of those is people management, the other is usually kind of P&L ownership.

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Do you think that had you stayed as chief of staff for longer, you could have found opportunities, opened up doors to get either one of those experiences, especially the kind of people management side that you just described?

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Or in your experience, was it kind of a capped environment and having made your way out of the role and stayed at Suzy, I mean, you reinvented your career kind of multiple times at Suzy, which is incredible, given the macro environment of most people kind of jumping ship every couple years.

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Do you think you could have learned the same skills as chief of staff?

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I think I probably would've had some skills that I would've gone deeper in, but I think as pertains to those two specific ones, people management and, and learning how to operate on a P&L.

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People management would've been tough for a company of our size, right? At the time, we were sixty people or so, and I think that would've been tough.

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I think if you're a big company and you're overseeing the office of the CEO or office of the CXO- Yeah, that's helpful context... that's probably doable, right?

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I think you can probably start to have folks who are there, and you can start to operate in a way that you could get that people management structure.

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But I think for us, that was probably a no-go relative to maybe one person here or there or something like not the scale of managing a few people and then tens of people and so on.

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I think as it pertains to P&L management, it's interesting because while at the time I probably thought I was managing a P&L, I think in reality it was like the peak of our zero interest rate era, and it was really-How do you spend more money to grow faster?

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[laughs] And like, I don't think we uttered the word cogs and profit for twenty-four months because it was all about growth. Grow, grow, grow. Like, get more salespeople.

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For us, it was get more consumers on our platform if we needed to hire another pod of a product manager and a couple engineers or anything.

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And so I think while I, I was exposed to the concept of P&L management, I think being a practitioner, I wasn't effective in it at the time.

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I think also in hindsight, like being a chief of staff, depending on the relationship that you have with your principal, you can get that P&L management and whether it's ownership and responsibility or probably more so just exposure and being able to provide a strategic look at it.

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Even now, like in a COO role, right, as we prepare for board meetings and I work with my CEO and my CFO, bringing a fresh perspective to the table now that I understand a P&L and what we're seeing and so on is really valuable, and I think a lot of chiefs of staff can do that.

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But I think oftentimes, at least in my experience, like principals are running so fast, they kind of assume people know how to manage a P&L, and they kind of assume that, yeah, yeah, it's just a bunch of spreadsheets and math, like you don't need to see it.

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And I think for many, right, I don't, I don't know people's relationships with their principals, but if they just ask, not only do I think that they'll have an opportunity to learn and see how different strategies and tactics that are being deployed at the business are impacting the P&L, but also they can provide a lot of value to the principal or to whoever they're working with, right, or the finance team or whomever, because they are involved in a lot of different things, and they do see like, "Oh my god, our gross margins went down by this many points," and nobody actually knows why because it's just a number on a spreadsheet without the context of what's actually going on in the business.

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But as a chief of staff, you do have your tentacles in so many areas, and whether you know the answer or you have a hypothesis, it's at least so helpful because at the end of the day, the purpose of a P&L is just to understand like where are we at and where do we wanna go, and if where do we wanna go isn't good enough, how do we change that trajectory, right?

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And so I think people management for us would've been tough at the size that we were, but I think in hindsight, I definitely could have double-clicked a little bit more into P&L management, even in my chief of staff role.

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I definitely agree with that.

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I mean, in my experience as a chief of staff, I wasn't owning a revenue stream directly, but just the very act of, say, putting together the board and investor presentations on a minimum quarterly basis.

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Sure, we had all the pretty graphs, but we needed to explain those graphs [laughs] and you know, what, what the change in numbers meant and how it was affecting the business and our projections and whether or not we were gonna hit those projections.

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And so all of my experience running a P&L, at least at that time, came from those exercises, and that was basically like going to business school and like kinda rapid fire and in real life. [laughs] Yeah.

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I can work with whomever and I can make any spreadsheet make up and go-- make a graph go up and to the right. [laughs] You know? Yeah.

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We can, we can pretty easily forecast the next twelve to twenty-four months to grow at just about any rate we want, right?

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But I think as chief of staff and then, you know, as now in COO role, but I think as chief of staff in particular, like you have an opportunity to be like, "So how are we gonna do that? Where are we putting our bets?

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Where are we putting our chips, right? Are we hiring more salespeople? If we hire more salespeople, like what's our success? What's our ramp time? Are we gonna go build out a new product to make a new product set?

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Like what do we think that's gonna look like?" And, you know, I don't think it's about getting it right, right?

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I think if you think you have a three to six-month ramp for salespeople, it's more important that you recognize that if we hire those people on January first, like they're not gonna be productive until July first, so like probably shouldn't have that ramp starting January fifteenth, right?

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And then I think the question then comes that I always try to pose is like, "What would help us blow this projection out of the water?"

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And I think that's where as long as you have some level of accuracy and understanding in a P&L and in your forecast and your projections as a chief of staff, um, and I think it's true for any executive really, but I think as a chief of staff, you can start to ask the questions like, "So how are we gonna minimize the risk and maximize the upside?

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Like what are the couple of things we're gonna do to actually make that happen? And then how do we stick to those decisions and really invest in them?"

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'Cause they're probably gonna involve some combination of hiring people or spending money on software or spending money on marketing or opening an office or whatever, whatever tactic or bet you might wanna make. Yeah.

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I will double down on that. As a chief of staff, whether you're junior or super senior, you still have the opportunity to kinda poke your head behind a lot of the closed doors that other employees just frankly can't.

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And that provides you almost unlimited context into what the business is doing, where time is being spent, what priorities are actually being prioritized, and if you're connecting the dots between the financials and where the time is going.

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As you said, as long as you're leaning in even further to say, "Hey, I recommend this," or, "I see a problem over here.

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Here's how we might be able to address it," that's really, I think, where leadership as a chief of staff starts to grow and other opportunities start to present themselves in terms of where you may step in after your tenure as a COS.

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Yeah. One of the things I talk a ton about to employees here at Suzy and then other folks that I talk to is like there's a pretty big difference between leadership and management.

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Like you don't have to manage people to be a leader, and I think that developing those leadership skills, whether it's about painting a vision, good communication, like bridging strategy to tactics, I can go on and on, right?

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Like those are skill sets that I think you can learn and demonstrate, like you said, whether you're fresh out of college as a chief of staff or you're a twenty-year vet as a chief of staff or anything else like that.

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Like you can be a leader at the company regardless of whether you manage zero or a hundred people, and I think sometimes people merge those two things together, and I think those are particularly true in like engineering and sales roles, but I think in the chief of staff role, you know, we talked about kind of being involved in everything and in charge of nothing, but that doesn't preclude you from going out and being a leader at the company.

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Let's talk a little bit more about kind of leadership lessons. You're now overseeing operations, HR, I think sales as a COO, right? You, you're seeing kind of a couple different divisions. R&D you said as well.

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You mentioned to me in our last chat a quote that stuck out, "As a leader, your job is not to make the trains run." Talk to me a little bit about kinda what that means to you.

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How do you kinda think about yourself now managing lots of people, but leading kind of these divisions forward within Suzy?That's my goal. I wouldn't say it's always true [laughs] but that's my goal, right?

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I think ultimately my goal, right, is to lay down-- to keep going with the analogy, is to lay down the tracks, pick the direction and how many trains are gonna be on the tracks, and then let the great people we have go be the conductors and figure out how they're gonna go do those things.

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And the only way they're gonna be able to do that, maybe even coming back to the beginning of our conversation, is to know the direction that we're going in, the main bets, the main priorities, and then keeping those people accountable.

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I think going back to my people management learnings, like I used to think keeping people accountable meant like, what's your number, whether you're in marketing or sales or engineering, everybody's got some sort of number, and like, I'm gonna stay on you every week talking about that number.

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And while I think that that can be effective in some places, I think in reality what I realized is like finding the right people in the first place who are accountable people versus teaching people how to be accountable has been far more impactful.

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And you hear this everywhere. Spend more time on finding the right people, make sure that the right people are in the seats, like all those sorts of things.

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And it really is so true because often what I've found is that, especially as I've moved into managing managers and managing VPs and so on, is like these people are awesome. They're really great, right?

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But there's an opportunity cost to having somebody who's good versus great, and your bar needs to be at great for that, right? You need to-- I think of it in two ways.

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One, like, I need a person who's a VP in X role to push beyond the bar I'm setting. I need to be the brake, not the gas pedal.

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If I'm the gas pedal, like we got a problem because I need them to be able to go and motivate their teams.

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And so I think ultimately when I look at my own leadership lessons and, and keeping the trains running, if you will, like if I'm day-to-day figuring out how to make sure we're hitting our roadmap or make sure we're having conversations at the right time or whatever my given role is at the time, like, I'm not spending my time and my mind space figuring out what the priorities are for the next quarter or the next year or whatever timeframe we're working on.

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And if that's the case, especially now when the world is changing so incredibly fast, like we're gonna hit a local maximum instead of a global maximum.

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As a venture-backed company, like nobody's interested in a local maximum, [laughs] right? Like it's to the moon or bust. And I think ultimately, like we gotta make those bets, and we gotta figure out where we're going.

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And I think a good example of this is something I wish we had, had moved on faster.

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Obviously, and this is gonna sound so obvious in hindsight, but like we didn't adapt to AI for internal operations or our product fast enough, and we did that because it wasn't good enough yet, if you will, right?

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And I'm sure a lot of the other-- I think a lot of people, right, and you know, who are like, okay, like we work with big enterprise companies, we work with banks and big CPG companies and so on.

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It's just not good enough yet. And that statement on its own was accurate, [laughs] right?

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Like you couldn't count the number of R's in the word Raspberry at the time and stuff like that, let alone do deep data analysis and, and so on.

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But if instead you tried to skate where the puck is going and say, "Well, what does that mean we need to do in terms of the people we hire, the product we build, the way we operate?"

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We would've moved much faster in taking that risk, and I think would've been in a different place. But that's hard because if you're too in the day-to-day, you don't see that and figure out what to do next.

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You're just trying to figure out how to iterate and optimize within, within the local area. That's really interesting.

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There's another thing that you shared with me, I think when you were a chief of staff, so we're talking five, six-plus years ago, which stuck with me for a long time, and it's something that we've reiterated to numerous chiefs of staff along the way, which is kinda splitting your time between business as usual work versus projects that move the company forward.

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I guess in thinking about your notes right now on, you know, how AI is shifting the business, that's clearly projects that move the company forward.

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Looking back at your chief of staff role, how did you think about splitting your time between kind of those two dynamics, and how has that shifted now in your COO role?

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I read something where somebody had articulated it nicely, which was like, in order to be successful, this isn't just as the chief of staff, but in order to like feel and be successful in your role, like spending seventy, eighty percent of your time just like kicking ass in your role, whatever that means, right?

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And obviously, the chief of staff, it depends who your principal for and what their needs are and how you're a foil to them and so on is important.

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Like let's not overlook that for the, the sexy future-facing stuff, if you will.

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But ensuring that you're then spending twenty-plus percent of your time moving the needle forward in some capacity, that could be learning a new skill, that could be working with a new team, that could be talking with customers, whatever the need is, I think is really important.

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What I think now is true though, and it varies by different roles, is I think we can now spend a lot more time figuring out the next problem to solve and more time mitigating the risk that you're picking the wrong problem because AI and automation can do so much more in the business as usual front.

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I think, for example, let's say you're in sales. I don't think the best use of AI and automation is that if you used to send out a hundred cold emails to just go send out two hundred cold emails.

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I think the best use of AI and automation is to go find the right hundred and twenty people to reach out to and go find those people.

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And I think that that's a microcosm for a lot of these things, which is now I think I could spend more time, and sometimes that means big-picture thinking, and sometimes that means...

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I don't know, this week we had a, a hackathon with our R&D team, and, you know, I got my hands dirty in Replit and started building products in a way that I hadn't done before. And sometimes it's that, right?

237
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So it doesn't just have to be big-picture thinking and strategy and, and that sort of thing.

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But I do think these new tools and technology have afforded us the ability to spend less time still delivering the same impact on that business as usual work, but more time saying, "Okay, what problem are we gonna solve next?"

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And I think those are how a lot of companies, a lot of people are gonna win in today's day and age is by spending more time figuring out what problem to solve as opposed to worrying about how to solve the problem.

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We talked a lot with our engineers this week, for example, which is like, you might be typing a lot fewer lines of code, but we need your specialized engineering brain who does great systems thinking and architecture and so on to spend more time saying, like, "How do we best implement this solution?

241
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And is this the best solution for us to be implementing," right? And yeah, now the business as usual stuff, which was you typing and writing code, ninety percent of it doesn't need to happen in the same way anymore.

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But making sure that we're building the right things in the first place has become more and more impactful in a world where, one, we have to move faster, but two, you know, it's become easier to do all this stuff, to go send a sales email, to go build a product or anything like that.

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And so I think from now my role as COO, you know, I try to do that across the company, which is like-How do we get each part of the company and all the leaders at the company to ensure that they're spending the right time moving the needle forward instead of just going out and saving those renewals or just going out and building the product?

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How do we make sure that our HR team is thinking ahead of the curve and going out and finding the right people?

245
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And I think that maybe instead of eighty/twenty, it's closer to sixty/forty, seventy-five/twenty-five, or something like that.

246
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But again, that doesn't mean doing less BAU, and it doesn't mean just doubling the stuff you were doing by, like, getting an AISDR or something like that.

247
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I think it does mean, though, you know, spending a little bit more time critically thinking about what problem we're solving in the first place. Yeah. I, I like this idea for the kind of BAU projects.

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It's all about zooming in and thinking about, you know, how can we do this differently? Are we solving the right problem? Can these technologies impact the way that we approach this, you know, sans any human involvement?

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And that's a very different, very first principles way of kinda thinking about how that work gets done. It then opens up the world, obviously, to focus more on what are the big shifts that we can make in the business.

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The other thing that is worth talking about is, as a chief of staff, you're often the lone wolf [chuckles] doing the things on your own. There is no kinda direct team involvement.

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You now have the capacity, and some might even call it a luxury, looking at it from the other side, of delegation, right, and being able to bring in other team members who may have more capacity or more experience doing some of this work.

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How has that been kind of a theme in your growth? What's been the hardest part about shifting from doing all the work yourself to now coaching others to do it with you?

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I think the way I got over that, and saying I'm over it is probably a little hyperbolic 'cause delegation is still challenging, right?

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But the way I, I started to, I think, get over it is when I started to realize that when I delegated to folks who knew what the hell they were doing, they did it significantly better than me.

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[laughs] That builds your ability to trust, I guess. Yeah. And seeing that happen made me realize, like, okay, if I'm delegating ten things, it doesn't mean all ten are gonna happen as fast or as good as I want.

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But if eight of those things are actually happening as fast and better than I want, then I now just have to turn my attention to two of them and make sure that I can course-correct those things.

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And so I think that for me, going from chief of staff, I'm doing everything to that style of delegation, you know, it's been five, six, seven years and still something I'm, I'm trying to figure out and find the right balance on.

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I think the other thing that it's required is when I first think I started delegating, I was doing so pretty ineffectively just by saying, "Hey, here's a task. I need you to go do it." Like, "Can you take this on?"

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And what that ends up missing is so much of the context of, like, why that thing is important.

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And so I think for me as a leader, it's always important to say, "Hey, I need you to go do X, Y, and Z, but here's why I need you to do that."

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And not everything that you delegate is gonna be business changing and super cool and, and whatever, but, like, if someone's gonna take on a thing, making sure they understand the why behind it I think is, is really important.

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And when I was the person in charge of doing the thing, I never had to do that. [chuckles] I always knew the why 'cause I was the person who was involved in the thing and then taking the thing on.

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And so I think that that's been a pretty major shift. And honestly, sometimes if I don't know the why, it forces me to say, like, "Hey, is this thing even really worth doing in the first place?" Yeah.

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It's a whole different view in terms of prioritization to have to kind of put yourself in the other person's shoes and thinking about, you know, is this even worth approaching. Yeah. For sure.

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Brian, looking back at your whole journey, chief of staff, biz dev, product, strategy and ops, now COO, what's the thread that kinda ties it all together for you?

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I think for me, honestly, the thread has just been how do I, whether it's as an individual or as a manager or someone building a product or anything like that, drive leverage in the business?

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And I think that's only getting more and more true, right, as you see all these companies have millions of dollars of ARR or FTE and so on and so forth.

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But to me, like, if I as an individual am producing one unit of output, like, that's not good enough, right?

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If I as an individual and I have a team of one person and we together are producing two units of output, like, that's not good enough. And the ways to drive leverage could be by picking the right priorities.

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It could be through building great products.

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It could be through the operating cadence and making sure that one plus one in different parts of the business, like the product strategy and the go-to-market strategy come together.

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But ultimately, whether I was in chief of staff, whether I was overseeing a business unit, whether I was in strategy and operations, whether now in my role as COO, how do I effectively drive leverage in the business is kind of that thread that I've been going.

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And I think frankly, that's why I found sales to be something that I was good. I wasn't the best salesperson.

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I was good, but, like, I wasn't the best salesperson, but, you know, not as my future per se because I think great salespeople could be 10X, right?

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And I think that's awesome, but I think for me, I saw other areas and ways that I could most drive leverage in the business and areas to learn from.

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And so I think for me, I'm constantly thinking of, like, this thing that I'm going to take on, is it going to be driving leverage in the business?

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Or to go back from before, like, is it just gonna help us hit a local maximum? And I think there's so many good ideas out there.

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Now with AI, every idea is so much more accessible that taking a moment to really think about is this the right problem to solve to drive leverage has probably been that thread. That's awesome.

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And I think your kinda generalist background has been carried through all of that to be able to make those the right decisions more often than not. I hope so. I hope the right decisions more often than not. Yeah.

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[laughs] Brian, it was really nice talking with you today. I appreciate you joining. Awesome, Scott. Thank you. This was fun. Thanks again for Brian Silverman joining us today.

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A few things that stuck out with me from this conversation. First was the way Brian talked about moving from chief of staff into his next role.

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It wasn't because he was looking to leave, it was because he saw a problem in the business that needed more than a chief of staff to solve. And I think that's a pattern I've seen with a lot of successful transitions.

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If you don't plan your exit, you kind of earn it by leading into something that matters. Second, this idea of driving leverage.

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Brian kept coming back to that as a thread through his whole career, not just doing the work, but asking whether the work you're doing is actually creating outsized impact.

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It's a really useful lens for anyone, but especially for chiefs of staff who can easily get pulled in a hundred different directions. And third was his point about delegation.

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It's not about handing off tasks, it's about sharing the why, and that's sometimes if you can't explain the why, maybe the thing isn't worth doing in the first place.

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If you enjoyed this episode, share it with the chief of staff you know, and if you're not already a member of the Chief of Staff Network, come check us out.

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We've got a community of over nine hundred chiefs of staff from companies like Microsoft, Google, Apple, Meta, and a lot more. That's it for today. Thanks for listening, and I'll see you on the next one.

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