In this interview, Rowan Trollope, former senior vice president and general manager now CEO of Five9, explains how the role of CEO differs from senior executive positions, emphasizing that the CEO alone defines company culture and holds ultimate decision‑making authority. He describes his own practice of fostering transparency by creating an open Slack channel where any employee can ask him questions directly, bypassing traditional communications layers. Trollope contrasts this approach with the insular, "us‑versus‑them" cultures he observed at companies like Facebook and Uber, noting that such competitive mindsets can create blind spots and hinder self‑correction. He highlights the danger of multiple sub‑cultures—silos or tribalism—within an organization, arguing that a single, coherent culture is essential for alignment and growth. The conversation also touches on the practical impact of his transition to CEO, such as a reduced staff headcount and the ability to make decisions without needing approval from higher‑up executives.
Chapters
How's life changed? I mean, when you're— oh yeah, because what were you, a VP or EVP? What was the title?
So I reported to the CEO. I was a senior vice president, but general manager is the key.
Ah, GM is over there with it. So what's the difference between, you know, sitting in the throne versus, you know, be on the right hand of the throne, so to speak?
There's no one, there's no one, you know, it's like one of the biggest differences is, uh, there's no decision you can't make. And, you know, when you're when you're number 2 at a Cisco or a Microsoft or, you know, any of these big companies, you don't define the culture. I mean, you work for the CEO. The CEO defines culture. That is like, make no mistake. And if you, if you get that wrong, it's like bad things happen, right? Because you can't have 2 people setting culture or 3 people setting culture. So that's like the hugest difference in my company now. I said, you know, the culture comes from me and you know that. So there's no one that can tell me no, which is nice. There's— you didn't— I didn't have to check in with anyone at my new— in my new job. The last job, you know, um, well, there's downsides of being a much smaller company, but there's also a lot of upsides to it. So there's this dimension of—
1,000.
1,000. Oh wow.
So you, you took over the top slot and lost 80% of your staff.
Staff. Yeah, it's much nicer. It's— I don't— it's less work for me.
You still can't know everybody, but you can know a lot of people. You can know maybe 300 people, 400 people.
Yeah, I have a, I have a channel on Slack that I created, all 1,000 people ask me anything 24/7. I'll answer them instantly.
I did. There's literally an Ask Jason on Inside Slack where I just said, listen, just if you got a question, just ask it. F it. Like, we're— that's like the kind of the new culture of business, which is like, stop looking at the CEO as the god queen or god king because they're not. You probably know the answer to your own question.
Exactly.
You're probably just scared of being fired, and that's why you're not just making a goddamn decision.
And I encourage people to post up there and I will answer directly, unpolished. There's no comms people typing my answers. There's none of that, right? It's just direct.
What got Facebook in trouble? Like Facebook is so inauthentic that you're like—
You mean in the culture?
The culture.
In their company culture.
The communication.
Oh, okay. I haven't seen it.
It was very insular. Like every, it's us versus the world.
Yeah, yeah.
Which was really good. Like that's a neat culture to, it's a very effective culture if you wanna beat everybody is to just have that, —crazy, like, competitive.
Same as Uber.
Yeah, Uber, I think, had a circle-the-wagons mentality at times. It's fierce, but then it also leads to a blind spot, which is anytime criticism comes in, you're just like, well, that's just people who are trying to— Take us down. —take us down.
Yeah.
So we should ignore it. And in both companies, if you look at it, ignoring the critics was great for focus. Yeah. It was really bad for self-correcting unforced errors. I guess would be the way I would say it. You know what's interesting? You said something I think very profound, which just zipped by, and that's one of the reasons I love doing this podcast is I get 2 times a week to talk to really, really, really smart people who are in the field. You said you can't have more than one culture, and I realized, oh, there is a word for having more than one culture inside a company.
Silos or what? Tribalism. Tribalism, yeah.
And it's the worst effing thing you could ever have.
That's why acquisitions are so hard. You're buying a culture. Yeah. You can't, but you know, I've been through so many of those. You can't change that. You bring it in, it is what it is. And that's why so many acquisitions don't work.
