Transcript

Paul Ford Your voice is so loud.

Rich Ziade Alright, I’ll talk lower. 

Gina Trapani It’s been very good for Postlight though. [Paul laughs] Your voice being that loud. It’s a feature.

RZ On pause. Recording. [Gina laughs] [music ramps up, plays alone, fades out]

PF Rich!

RZ Paul!

PF Big news this week.

RZ Big good news?

PF Big good news.

RZ Tell me about the big good news.

PF I quit.

RZ Blegh. [Paul laughs] I meant to talk to you. I quit, too. 

PF Oh my God, what a crazy coincidence! What are we going to do with ourselves? 

RZ But that’s a good news quit.

PF It is a good news quit.

RZ Because they’ve got great leadership at Postlight that has stepped up.

PF Yeah, this is good news. We’re, I mean, let’s be clear. We’re gonna keep doing this podcast, so nobody has to worry.

RZ Don’t worry!

PF Don’t you worry. You’re going to hear our dulcet tones in your ears forever. But no, it was time we’re going to talk about that. And we’ll talk about we want to introduce you to the new leadership!

RZ At Postlight, yes. 

PF Pretty exciting. 

RZ Let’s do it. 

PF I’m freeeee!

RZ It’s bittersweet. More sweet than bitter for sure. Paul and myself have stepped down from running the Postlight machine. Postlight business.

PF That’s right. You used to be the President. I used to be the CEO. And now we’re both ready, let’s say together. 1, 2, 3…

PF & RZ Co-founders.

PF Yeah, once again.

RZ Yes. It’s a milestone, frankly, an achievement, cultivating and building a place where you can step aside and let others run it, I think is a really cool thing to do. It’s something that’s been cooking for a while.

PF Yeah. I mean, we started talking about this well over a year ago. 

RZ Yeah. Yeah. 

PF So I mean, you know, this is an interesting moment, right. And I think we made a choice to handle it in a very specific way, which is to take our time, to be really clear with each other about what we wanted. And we want to do on the other side, to acknowledge and really feel good about where we’d gotten the firm, like this place is almost 100 people now, it’s very successful, has a lovely office, we got it through a pandemic, we got it through the Trump presidency. We got it through all kinds of stuff. And then there is this point, and I don’t know what the point was for you. But for me, it was just like, I don’t need to keep doing what I’m doing as CEO, I don’t need to keep, like I felt I’d kind of proved my point.

RZ Yes, I think that’s part of it. But I think another part of it is, it’s funny. Success at this scale tends to test you in terms of success equals happiness, or success equals some happiness or less happiness as more success happens. The truth is, we both have been thinking about other leaders at Postlight. I’m actually proud of this about Postlight, partners can get fast tracked at Postlight. We tend to act quickly.

PF We’ve grown a bunch of careers.

RZ We’ve grown a bunch of careers. And we are not alone here today, Paul Ford. The new leadership of Postlight. In fact, we asked to borrow the office to record this podcast. So who is that new leadership? Paul?

PF Well, Gina Trapani is the new CEO of Postlight.

RZ Clap, clap, clap.

PF Clap, clap, clap. And Chris LoSacco is the new President of Postlight. Hello, Gina and Chris.

GT Hi!

Chris LoSacco Hey there. 

PF It’s awkward. 

GT It’s a little awkward.

PF No, I mean, taking power is awkward. It’s incredibly awkward.

CL This wasn’t an ousting. 

PF No, I know.

GT It wasn’t a coup. [Gina laughs]

PF But that’s why I’m you know—

RZ The best kind of coup doesn’t feel like a coup. [Rich laughs] We should get an origin story here. Both Gina and Chris are partners of Postlight. They’ve been partners for years, they’ve worked together incredibly well. So I’m gonna, I’m gonna go into interview mode. I’ll pose this question to both of you. We were kind of cryptic, sometimes consciously, sometimes less consciously about a clear path to this.

PF Well, what we did do is we set up a group, which we refer to as Strategy Group inside of the firm, what about a year and a half ago?And that group is responsible for a lot of the things that Rich and I used to do, which was sales being one example, growth, marketing, client relations, quality, managing the quality of all the deliverables. All the kind of like things that aren’t making products, but that you need to do for the agency to run. Got rolled up. Yeah. Because that’s what we did as leaders. And the two people who really naturally emerged saying, hey, let me take more of that, this wasn’t a very glamorous role when we created it, were Chris and Gina.

RZ I will say this, and then I want to pose the question. This wouldn’t have happened if it weren’t for the dynamic that Chris and Gina have. It’s worth saying, when you get to this level. The titles of CEO and President are pretty ambiguous, frankly. There are people that can fall into either roll and clearly have all the levers. It depends on the company, depends on the culture. There are no laws that dictate—

PF It’s very different what you and I used to do compared to what like Satya Nadella does in Microsoft, right? Like its CEO as a title can be anything. Same as President. President tends to be a little more operational. CEO is very ambiguous. 

RZ That’s right. So we had ideas. Was it a thing where you felt like you wanted it? Let me throw it to Gina first. Like, okay, I’m seeing the possibility here. Because we were cryptic.

PF Yeah what was that like, when you’re sort of like, do they want me to run the company? Like, what, how, what happened there?

GT It is very confusing. I mean, I could see that you were looking around and saying, like, what were the leaders that we have here? Or how does this business scale or you only scale business with with good leaders who can then activate things. So it’s very confusing, Because there were times and you’d be like, are you interested in taking more of a leadership role here at Postlight? And the answer to that question is always yes. But like, I would go home and say to my wife, like, I don’t know what that means. I don’t know if they know what that means. Or maybe they know, and they’re not telling me, maybe they know, and they want to hear it from me. I’m not sure.

PF All of the above, Gine. All of the above.

GT What it is like, there’s an opportunity here. I’m Postlight’s biggest fan, I love working with our clients, bad software deeply upsets me. I think that Chris and I really share that. And I was like, I’m gonna go for it. I want to, you know, see, see what happens here. And then there’s kind of a period, time when it was like, nothing really happened. And you know, it wasn’t like grabbing territory. And you were a little bit like, do you want this or not? And I was like, well—

RZ Yeah, that was a great moment.

GT It was a conversation.

RZ I want to dive into this for a second here. It was a wonderful chicken egg moment. Gina looked at me and she’s like, so what’s up? And I said, you need to step up if you really want to lead and she said, well, if you let me lead, then I’ll step up. I’m like, no, no, it doesn’t work that way. Like, you have to, like, stall the plane when you’re training. You got to do it. You got to show me you can do it and show us so that our comfort levels there and then we will do it. And Gina’s rationale was, well, you haven’t empowered me. So how can I do it? I’m like, well, I’m not gonna empower you to show me you can do it. And we went back and forth. [Gina laughs]

GT We did!

RZ It was a moment.

GT It was a moment.

RZ But actually, it was a clarifying moment, because I think you adjusted and I think I adjusted to some extent, I think that needed to be aired out. Because at this level, there’s no punch list. There is no clearly, okay, you know, we’re getting nines out of 10s down the list here, right. And so it’s a go there isn’t that. It’s very human. At this level, it is very human. And that handoff is very human. Chris, posed to you. I mean, I’ve been working, I mean, just real quick with Chris LoSacco for 211 years now.

PF Easily.

CL It’s been over 15 years. 

RZ Over 15 years, my past, my last agency, we work together, you worked at an Acquirer, which is a media company, and then came over to Postlight. Chris is one of the most thoughtful product thinkers I’ve ever worked with, but matured into an operational leader that thinks about all aspects of the business. Same question for you, like, did you feel like hmm, I think I’ve got an opening here. Did you see a path?

CL It was partially seeing a path? I think it was also the conversations that the four of us were having, you know, as the Digital Strategy Team was maturing, Gina and I just naturally moved closer to the center of the business, we were right thinking about the relationships, we were thinking about the team, we were thinking about how people went on client engagements, and it felt very, like a very natural evolution. And as we talked about, you know, some of the bigger initiatives that you two might focus on which we can get to in a minute, like it was very exciting and attractive to me to think about Gina and I taking the reins and saying, we see a future for this business, we’re gonna carry it forward and let you to, you know, make bigger bets, which was really exciting to us.

RZ Worth saying out loud. When you get to this altitude at just about every company, there’s a little bit of buying, there’s a little bit of posture, like positioning time with the power structure, like how do I get good face time with the people who can actually, people are ambitious. There wasn’t a lot of that here.

PF No I think if anything, I think people avoided spending time with us. I think that—[Rich & Paul laugh]

GT I mean, the partners at Postlight are all pretty apolitical. There’s not politics or land grabbing here. Or like we all we’re all pretty collaborative. I don’t know. We just isn’t that kind of culture.

PF Well, it doesn’t work with Rich and me. 

GT It doesn’t work on you. That is true.

PF We find it really unappealing, essentially, even though there is always power in the room, you want a peer dynamic because you’re focused on the work.

CL That’s right. And we really care about the work. I mean, I think that was one of the things that drew Gina and me closer to what what the business was doing was, you know, we like to work.

GT I mean, it was so clear to me from very early on that Rich and Paul, like the thing that would, you know, gain your favor or have you look upon me as someone who can be capable is the work. And this is I mean, this is advice I give to literally everybody who comes to me for advice in their career, you know, I want to get to senior this or I want to level up to that, it’s like, just do the work, focus on the work, don’t focus on the title, the title will follow. You just do the work, just show your value. And Chris really has that same ethic, and I read that really resonates with me. And I think part of the reason why he and I just work together, we also both just really enjoy the work. I think people sometimes want a title because they have this like notion of what a title means. And then it gives them status and you know, meaning in this world. And that’s a dark road, you don’t want to go down that road.

PF People always think and I can’t play them because I used to be there too. You think there’s secret knowledge in the world, there’s something you’re missing some detail, some some system of rules. And like we work on this pretty hard to try to make sure that we don’t do that. Now we aren’t that there isn’t this like secret way to get promoted, but rather than it’s, it’s pretty clear, and you worked hard, and you stuck around and you had some good days and some bad days, but they were mostly good. And then bam, you know, stuff starts to happen, which in agencies often can happen pretty quickly. So I think like, no, we don’t have that culture where people are sort of like, every now and then we’d be in this office and talking to somebody and I could feel people’s eyes on the window. [Gina laughs]

RZ That’s natural. It’s utterly natural and normal.

PF What’s happening in there? 

RZ Yeah, I think a little tidbit of advice at this altitude, schmoozing doesn’t work. 

CL That’s right. 

RZ At this altitude, it’s not that, you know, the bullshit meters off. It’s just that we’re so utterly consumed by the health of the business that telling me I have nice pants today—

PF Well, and detail doesn’t work that I think if anything, what made the leadership path clear to us was that you’re getting less and less detailed, but more and more assured with how you are communicating to us.

CL Yeah, I actually think we learned to do the opposite is not overwhelm you both with detail. And you know, grind through each little bullet point on the agenda. But instead say, here’s what you really need to care about. And don’t worry about the rest. We got it.

PF You were very confident in your own value, which actually is you can make that up in your life and be like, I’m a genius, but there was, it was earned.

GT It works for clients, too. [Gina laughs] That’s kind of part of our job. 

PF That’s right. No, that’s right.

RZ What’s the number one quality that you think helped get you here? First, Gina.

PF God! Well, I mean, she is a leader. So. Fine to put her in the hot seat.

RZ These are the kinds of bullshit questions that are going to get tossed to you now.

PF Yeah it’s true. [Gina laughs]

GT Oh, number one quality. Gosh, this feels like a bad interview question Rich. I’m like, like candidate interview questions. 

RZ If you don’t want to answer it, I’ll answer it for you. [Gina laughs]

PF Wow, this is a great interview.

GT Says the owner of the business who promoted me to CEO. 

PF If you ever wanted to be the most stereotypical version of yourself—

RZ No, but I do think, look, let’s lay this out. I mean, if Paul and I didn’t give you these titles, you wouldn’t have them. Right. They were handed to you. And there are certain qualities, I think, first of all, you’re both incredibly complimentary. You have strengths that complement each other’s weaknesses in a very, frankly, it’s just dumb luck that we ended up here that you guys work so well together, and you’re complimentary. But do you have an answer? Gina, I still, I just gave you a bunch of some time there. I can answer it for you if you want.

GT I do. I do. There was a moment in my time here at Postlight where Rich and Paul, you were both very confusing to me, I didn’t know what you spent your time thinking about or talking about you were in another room with the door closed. And I don’t know in the kitchen, or in a casual conversation, you said something about how you were a little concerned the pipeline, the sales pipeline felt a little dry. And I said, I thought to myself, I don’t know what that means, I’m going to ask a little bit more. And that started a conversation that made the big shift for me, which is that I had to shift into an owner’s mindset, which is very weird and difficult to do when you’re an employee allocated to a project, you just don’t have a whole lot of visibility, even to the notion of being you know, an owner or part of like thinking like an owner of Postlight the business was foreign, you know, felt like this giant entity that I was just one small part of but I had to make that shift and I think that once I started to try to understand, like be in your shoes and think like an owner and think about like the business and you know, outside of my individual emotions ambitions, my teammates have visual individual emotions, ambitions. Look at it from that altitude. That was a big shift for me. And I think that you to start to see me make that shift and go like, oh, that’s interesting!