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Six months ago, Gina Trapani and Chris LoSacco took over as CEO and President of Postlight, respectively. This week, they join Paul and Rich to discuss their new roles, the leadership transition, and why Gina thought it might never happen. Chris and Gina also share their vision for Postlight’s future and what they’ll tackle first. Here’s to a new year and new opportunities!

Transcript

PostlightPodcast_Episode312

Paul Ford No, no longer CEO. Agencies are hard to run. It is a brutal business.

Gina Trapani Great! Thanks!

PF Yeah, just a nightmare. Just like looking into a chasm that looks back at you and says, “I will take your whole soul” [laughing in background]. It’s great. And you’re doing great. I just want—you guys keep getting paler every day, [more boisterous laughter] which is confusing.

[00:18-00:32 Intro music]

Rich Ziade Hey Paul! How are you? 

PF Oh, boy, my bursitis. No, I’m fine! Thank you! Everything is well, I don’t have bursitis, gettin’ ready for the holidays as we’re recording this. I got a sandwich I’m excited about once we’re done recording. Kind of the healthy option, so feelin’ pretty good overall, how about you? [Music fades out]

RZ I’m doing well. I’m actually in a very centred, peaceful place. 

PF Yeah, well, you’re not in the office. You know, you’re working from home, so maybe that’s it [Rich laughs]. Maybe that’s your centred, peaceful place.

RZ That could be it. There’s another reason I’m in a centred, peaceful place, Paul. Do you know why? 

PF You got a really nice curved monitor for Flight Simulator? 

RZ Reason number one. Reason number two is that we have actually executed on one of the smoothest leadership transitions in the history of business, in the history of—

PF Very proud of this. Very proud of this. You and I do not run Postlight day to day. At all. Anymore. For real. 

RZ We don’t. Yes.

PF Right? Most of these transitions, I think, it’s like, “Well, who pulls the strings?!” And, I mean, we do, we pull strings but we do it in a—like every two weeks we have our string pulling meeting. It’s very uh—

RZ A lot of the times we pull on a string and realize there’s nothing at the other end. And you’re not actually impacting anything. But you pull anyway [laughs]. 

PF Yeah, yeah, absolutely. So, look, what we’re talking about is that the company—the president and CEO of the company used to be you and me and now the president of the company is Chris LoSacco and the CEO is Gina Trapani. I’m gonna tell you, there’s an amazing coincidence: those two people happen to be on the podcast right now. Chris and Gina, hello, welcome. Welcome to the Postlight podcast that you also are hosts of.

[2:06]

GT Thank you, Paul. 

Chris LoSacco Hello.

GT I’m realizing that compared to the HBO show, our podcast episode about succession is gonna be so boring. 

CL Mmm.

GT There just wasn’t a whole lotta drama. I’m realizing like, mmm, this gonna be—we’re gonna talk about how well this thing went. 

PF There wasn’t any drama that was public or recorded. I’m sure there was plenty of drama [Chris and Gina laughing] as you thought, “How will you be taking—” You know—you know, it’s it’s—Rich and I were very confident in our roles. So there’s—there’s a little of that but that’s for the book, later, when Postlight is a 10,000 person company. 

CL We have our message retention policy in Slack set to 30 days, so who knows? 

PF Yeah, that’s right. 

GT If it happened more than 30 days ago, there’s no memory of it. 

PF Oh, let the DMs go to DM heaven. That is very, very important for any—

GT It’s a wonderful thing. Slack retention is a wonderful thing. 

PF Can I talk to you for a minute? How many DMs during the transition started with those? That like, “Hey, can I talk to you for a minute?” 

CL You know what’s in a lot of mine? A lot of mine there’s no context because they’re happening in a meeting where I’ve just [Paul laughs] gotten completely frustrated. And it just says things like, “Is he serious?” Question mark. 

PF Yeah, question mark, question mark, question mark. 

CL Yeah! And I have no idea which meeting or—I’d have to triangulate against the calendar. 

PF Two hours later I come back and just write “lol”. Right? Like—[everyone laughing]

[3:23]

GT Chris and I do the same and then I start a thread and go, “Wait, what was this about? Was this about that thing?” And he’d be like, “Yes,” or be like, “No, no, that other thing!” So we have to sort of go back and figure—I always have to know what exactly he was referring to. 

PF There is an element of running a company that is like being a diplomat in France in the eighteenth century where you’re just like, “Well, you know, how is the weather?” And that actually means that something really bad is about to happen, right? All very subtle cues, especially in client services. Anyway.

RZ I wanna actually ask a question to Chris and Gina, just to recap for everyone listening, in June—this happened in June, almost exactly in the middle of the year. And I’ve never asked you guys this, so I’ll ask you now, live: you know, what was day two like? Like you had the big announcement, I happened to be out of the country at the time, but it was big. It was a big deal. It was a big moment. I mean, it was just said out loud one day and I mean obviously the planning had been going on for a while, so that happens, what was day two like? What was actually hour two like, when you hung up on that all-hands meeting? 

GT Well, you know, it’s that thing where, like, we had been planning for so long and working toward this thing for so long that the transition moment was a moment to get to. I had to keep reminding myself—

PF I gotta interrupt you because Rich and I thought it was going incredibly fast and later [Gina laughs] we found out that you guys were like, “That took forever! That whole transition!” 

GT It was super fast for you, super long for us, and for me, I was like, “Oh, I didn’t just make it to the finish line. I made it to the starting line!” Like, that was hour two for me, right? 

PF Yeah.

GT And, you know, for me, like, the profound responsibility that this role is, like it was not lost on me. And honestly, if I didn’t have that feeling of profound responsibility, I’d be the wrong person. But I could see that you both were managing your own feelings about letting go and handing over a little bit of control and seeing people who, you know, might do things slightly differently than the way that you would do them and the feelings around this. I have had people take over things that I started before in the past. I know what that feeling is like, and being aware that those are feelings and wanted to show you, like, “We’ve got this. You don’t have to worry.” But also dealing with my own feelings of, like, “This is a profound responsibility and I need to do a good job and show up in all these ways.” And like all your strengths and weaknesses, like, it’s like a magnifying glass, you know? 

CL Mm hmm. 

[5:39]

GT And sometimes it’s like the sun shining through, just burning [others laughing] you on the weaknesses, you know? That’s what hour two was like for me. 


RZ Let’s make this extra fun, even for people who work at Postlight. I’m gonna tell a story that no one knows about. 

GT Oh boy!

RZ The transition happened in June. Around April, it was a Friday morning, and Paul and I asked for 30 minutes with Chris and Gina and we had a presentation where we laid out the 14 reasons it wasn’t time yet and certain things that needed to happen [Gina starts laughing]. 

CL Oh I remember this meeting. 

RZ You remember this meeting. And I—all I saw on Chris and Gina’s face was, “This is never gonna happen.” [Laughs boisterously]

CL Yeah. Yeah, no, I mean. 

GT There was a possibility that it wasn’t going to happen up until the words came out of your mouth at the all-hands. Like, I was fully expecting the morning of the all-hands for you two to be like, “You know what? We thought about it and this isn’t the time.” 

RZ I think what a lot of it was—By the way, I don’t—I think that was the right meeting. I think it was the right pause because I realize—you realize when you start your own business is that you don’t say a lot of things out loud, you just do stuff. There’s not a lot of documentation, there’s not a lot of protocol, there’s not a lot of anything. 

PF Especially early days, right? Like, I mean, it’s just Postlight was a very, very different company every single year. Those first like, four years. 

RZ Those bullets were listed in my head, reflecting on the ceiling as I looked up from my pillow. Because they were things that I had never articulated. They weren’t—it wasn’t a move to stall the transition. It wasn’t actually the transition itself, it happened to be a lot of change: two partners, two, like, founding partners had departed, there were some vacuums here and there. It was a lot! Right? And it was like, “Hold on, we gotta check about seven more boxes here.” Is what ended up happening. Tell us about you guys comin’ into that meeting and then comin’ out of it, I mean that had to feel good. 

[7:34]

PF No, because at that point, just for background, like, we really talked very openly about this, we were getting a transition plan in place, and Rich sat down. You and I workshopped this before it came through, and, you know, I was like, “Look, my take on this whole thing—” I had a funny role in all of this, before you guys answer this question, which was, “I will not facilitate any communication between all of these parties.” And when the transition happened, it had to happen on its terms, there could be no coaching. People had to talk about where they were at and if where they were at was the reality of the transition. If Rich wasn’t ready to go, if I wasn’t ready to go, if you weren’t ready to go, then it wasn’t going to happen. Because that’s all—it’s human beings saying, “I’m ready to let go,” and another person saying, “I’m ready to stand up.” So, Rich was like, “I have to do this.” I was like, “Then you have to do it. Let’s do it and talk it through.” You came in thinking, like, “Ok, we’re moving forward, tentatively, step by step.” How did you feel that day?

GT The thing that you, Rich and Paul, had been so good about the whole time that we’ve worked together is that you center rationale for the things we do at the company around what’s good for the business. It was not about my personal feelings. My personal feelings about delaying the transition were inconsequential, it didn’t matter. Like, what mattered was the company and the team and the stability of the business. So, to tell you the honest truth, I don’t—I don’t remember this particular meeting specifically. 

PF Oh you know, we have a bunch of them. 

GT We had a lot of meetings, you know, up to the transition where there—all the things that we had to—you know, all the boxes that we had to check before we actually did it, so I don’t actually remember this particular meeting, but—but, you know, there’s like my personal feelings in the moment, like, “Ugh! This is taking so long! I just wanna get to—I wanna do this thing.” And then there’s like, “But wait, there’s some really good points here. We do need to address these issues in the business, right?” Cuz—and that’s something that, you know, is this good for Postlight? What’s best for Postlight? That’s something that I think you’ve really, you know, imbued in me and Chris—

CL Totally.

GT We say that to one another a lot. 

CL Going through a leadership transition, it’s very fascinating because there’s like the Rich and Paul way of doing things that has worked really well for Postlight for five and a half years—six years. And then there’s, like, the Gina and Chris way of doing things, and there’s a good amount of overlap, that venn diagram, there’s a lot in the middle of the venn diagram [Paul goes, “Hmm”] but there are things that are different and, I think, one of the negotiations, so to speak, that we were doing as we lead up to the transition, and frankly even a little bit after the transition is, how do we let go of some of the things where we differ and the Chris and Gina way is gonna be a little bit different, you know? Marketing comes to mind. We had a new marketing leader coming in right as this transition was happening and there were a lot of thoughts that you guys had about what should be happening and then there was a slightly different way that Gina and I wanted to approach it and so we had to, like, work through that together. And—

[10:29]

PF We’re tech and product people, right? We craft the interface. So, actually, what happened was a set of interfaces emerged—

GT Yes.

PF—so that, like, Gina Chris Co. and Paul Rich Co. could exchange information. It’s not, like, utterly dispassionate. It’s still the same company and the same conversations. It’s just like us going, “Hey, we need this.” And you’re going, “Ok, lemme provide that,” and sort of vice versa as well. That’s what emerged after the transition.

CL Yeah!

PF You couldn’t really do that before. 

CL Some things got more formal but it was, I think, good. Like, you know, we—we buttoned up a lot of things—

PF Formal, scaleable. 

CL Formal, scaleable. 

GT It is! And it’s funny, Chris and I have really taken that—some of that formality to our senior leadership team, you know? 

CL Yup. 

GT Like, we’re not a thirty-person company where you can sort of casually make a decision that has a big impact on the group, you know, just in a conversation, we ask people, like, “Can you put together a proposal? Can you walk us through it?” And I think that’s a good thing. 

PF I mean, for the first five years, I loved to communicate through memo and writing, and one of the great tragedies of my role as CEO is that in a small organization, everyone is functionally illiterate, doesn’t matter if they have 25, you know, PhDs in English. They just—no one seems to be capable of reading anything longer than a paragraph and acting on it. . . in a Slack message. As things scale up, documents—and presentations become more and more important. And that—that has really evolved—“No, this isn’t gonna work—” That communicate—We have a megadeck that is the template for how we communicate internally and externally, and I’ve seen Google Docs with plans on them that I think people are reading and acting on. Like it’s—it’s very, very different because it used to be to effect change at Postlight, you had to simply—you sat down and you talked to people, and you talked to them enough that they then would enact that change. It was really funny—it was like—almost like society forming. It was very interesting to see. 

[12:00]

RZ One of the ways that I sort of processed the change was coming to understand—I find comfort in control. The way I see—

PF No!!! No!!! Are you kidding?!?

CL That’s so surprising!

GT I’m shocked! We’ve worked together for so long and I just didn’t know!

RZ This beautifully illustrates the comfortable rapport between the four of us [others laugh boisterously]. 

PF No, we joke about—like we have metaphors for—I always refer to it as bone-in-mouth, like just a dog, “Arrrrr!” [Others chuckling]

RZ Also very flattering. Most of the time, and you guys know this is happening, because we’ll meet and then Paul and I will talk about how you’re managing the company [Gina and Chris laugh]. Right.

PF It’s wonderful, right? It’s a great feeling? 

RZ 80% of the time, you got it right. Saying that out loud, not flattering you, I wouldn’t’ve done it much differently. 

GT What is that like a B+? 

PF That’s a C+. 

RZ Three percent of the time, you get it wrong. Do you know what the other 17% is, Gina? So 80 is right, 3 is wrong, there’s 17 left. You know what the 17 is? 

GT Uh, I don’t know but I hope it’s good [laughing]. 

RZ The 17 starts like this: why would they not do that? And what that speaks to—

PF Woah, you just described 80 percent of my Slack messages from you. 

[13:38]

RZ [Laughs] What that speaks to is my own issues with how I process change and how I would go and do things. It’s such a preposterous question to ask why you wouldn’t change the color scheme to mint green without ever talking to you, and never assuming you should do it ever, is insane! It’s fully, entirely insane. God bless Paul Ford because for whatever reason he tends to just fan the flames of me asking why you didn’t do something [chuckling]. I don’t know if he does it to make me feel—to calm down. Sometimes he just responds with, “It’s Saturday.” [Laughs]

PF No, no, no—Fan—fan the flames—I tend to put water on the flames, not fan—fanning the flames makes them larger. 

RZ It’s a dialogue. Sometimes they pierce through, sometimes we—and we have done it, and we’ve tried to be reserved. We come back to you and say, “We think you need to do more of this.” Or, “We think you should think about that differently.” 

PF Let me actually explain what happens there, right? Cuz it’s—you and I are friends, our children play together, and I think we will be friends for a very long time in our life. We have that dynamic and that’s a big part of our interaction. But there is another element where we—because we’re professionals together, we kind of assign each other work. But you can’t really do that as peers, that’s really tricky. I trust your paranoia very much and I learned to trust it the hard way because I came in like, “Oh! You know! You we’re gonna build a company based on puppies and hugs!” And you were like, [in a deep, ominous tone:] “No!” And over time I realized that there is actually room for probable more puppies and hugs than you might’ve expected but at the same time, your paranoid instincts as an operator sure were validated by events way more times around things like contracts, proposals, execution, all these sort of aspects of running a business, especially as we got bigger, that it just kinda—just grisly. You were in there, and you’d be like, “Ah! Bah bah bah bah!” And you’d get all upset and I’d be like, “What’s he talkin’ about now?” And then like six weeks later—and I know that Gina and Chris have had this experience, it’s very frustrating when somebody’s right. But your paranoia is very, very valuable. So, I feel that my job as your business partner is to not suppress that instinct but just, like, listen to it thoroughly, not internalize, not let my own anxiety go up, but then think about, like, “Ok, what is this telling us? And how can I go back to Rich and how can I go to other people and kind of get people to act and see this without maybe the sense of urgency and panic that it might’ve come across in the initial communication?” And I actually, like, this is now a healthy dynamic in my life. I think that this is a really good use of you in an organization. 

RZ You mean, between you and I. 

PF Yes! And also just like, it’s good for Postlight. 

RZ Well, is it? I mean that’s what I wanna ask Chris and Gina—

PF It’s not good if it’s directly coming from you, and fanning out to the organization. I think it’s ok if it’s coming to me and then we filter it together. 

[16:22]

RZ Gina and Chris, I mean, answer separately. I mean a lot of this about instinct. I can’t write a three-pager that hands over a set of instincts that if you just read it, you have the instincts. Talk to us about that intangible and how you think about it. Cuz instincts drive decision-making, right? Decision-making doesn’t just happen cuz there’s an owner’s manual. Cuz this is a wild business. The agency business, for those that are not in the agency business listening to this podcast: it’s a wild business. Right? So, there’s no manual. How do you cultivate those instincts? How do you start to listen to them? How do you act on them? 

GT I mean, let’s say, the important thing, which is that you develop instincts through years of experience. So, from a sheer number of years of experience that you, Rich, have been in the agency business than I’ve been in the agency business, there’s just a big delta there, right? And with experience, you develop judgement, you develop history, you develop scars. And you’re like, “I’m never gonna cut myself there again.” That happens over time and it isn’t something you can communicate in a three-page memo. So, I mean Chris and I will always take you and Paul’s thoughts and feedback and suggestions with full, open hearts because you have—you put in the years. I mean, you started this thing, right? You put in years that—in a position that we didn’t. You know, by the time it gets to us apparently it’s filtered through Paul. You know, if you send us five bullet points [Paul laughs, Rich joins], it’s human to be like, “Ah, ok, great, like—you know, [chuckles] we have to now deal with this feedback.” But then usually we talk through it, we take two and say, “They didn’t have context, this doesn’t matter, but these three [mm hmm] are really good points.” And Chris and I have sent each other a bunch of times, “It’s annoying that Rich is so right so often. Like, he’s right about this and it’s annoying that he’s right about this and that we didn’t catch it but we should take this feedback and act on it.” And we do!

RZ We’re actually saying something without saying the actual words, so let’s say the actual words: you don’t report to us. We don’t have directives. You have goals. High-level, high altitude goals but Paul and I meet with you once a week, it’s semi-structured, catchin’ up on some key things but you don’t report to us. We don’t assign you work; you don’t have directives that you have to go execute on. In fact, you’ve started to build a very particular muscle that took me years to build which is you sort of nod at some requests that aren’t actual requests, that sound like suggestions but are meant to be pushier than suggestions, and you hope we forget about them, and sometimes we do. And that’s a very powerful thing. 

PF You also increasingly—they know what’s coming. I’ve seen some definite swoop-ins like mid-meeting, where they’re like, “Great, Rich, we’ll talk about that with you later.” [Chuckling] [Yeah] They know. 

[18:55]

RZ This is all with a wink but, look, [yeah] managing that and understanding and apprec—This melts down if we don’t give the leadership that autonomy and there isn’t a dynamic where we can talk to each other but it’s clear that ownership is what it is. Like, you know, people at Postlight don’t know this—They don’t know. Nobody knows the actual power dynamics. We’ve got 120 plus people at Postlight, there’s probably 120 different perspectives on how the working relationship is, right? But I think as time goes by it’s becoming clearer and clearer that you guys have taken the wheel. And I think you guys wanted that. I think you wanted the wheel. 

CL Yeah. 

RZ So, here’s a really hard question for each of you: give us an example of something like, “Man, as soon as I get the wheel, I’m gonna stop doin’ that. Or I’m gonna change that. I’m gonna bring an end to that bullshit.” [Gina laughs boisterously]

PF Oof. 

RZ Gina’s opening up! 

PF Yeah!

GT I actually—I wanna hand this to Chris because in our first like week, Chris and I we meet—our meetings are very casual: they’re conversations, we’re—

CL We do a lot of async.

GT—a written people, so we have a constant—we do a lot of async. We have a constantly running agenda where we write to one another versus meet. But he shows up in a meeting with me and he says, “There’s somethin’ . . .that I wanna talk you through and I have a deck.” So now, this is unusual [laughs]. 

RZ You make decks! 

GT So he’ll present a deck to me, ok? 

RZ For each other?

GT Yeah, so he’s presenting a deck. And so he brings up this deck. The first slide is a photo of his degree in theatre and he says, “I wanna caveat this whole presentation with this: I have a theatre degree.” And I said, “Yes, I know this about you.” I have an English degree, just so everyone knows, in creative writing. And I said, “Ok, Chris,” and I’m like, “What’s about to come?” And then Chris, I want you to talk through—it was like all of your frustrations with the way that things worked at Postlight. Like, here’s how we’re gonna fix them.” 

[20:49]

RZ [Laughs boisterously] Can you please share this deck—

CL No! 

RZ—with us? Please? [Everyone laughing]

PF No, we’re never seeing that deck, Rich. I don’t wanna see the deck. [Rich laughing]

CL It’s important to preface—

PF No, I’ll tell ya: I’d be fine with the deck but it would just be like my Slack would be screenshots of the deck [everyone laughs] for like four straight weeks. I don’t have it in me.

CL Look: there were bits about operationally, how we were running this business that I wanted to clean up. We wanted to clean up. And it’s so funny because, you know, the things that make you good are also your biggest blindspots. And I can’t help but want things to run really efficiently. LIke, down to the cell in the spreadsheet, right? How are we collecting every dollar within the 15 or 30 days—

PF When it’s time to procure software, people should talk to Chris LoSacco. 

CL I mean, this is the thing: I want our tools to be great. We are software people! Like, the whole reason that we do what we do is to make our software better. 

RZ This could’ve been anything. I didn’t know where this was going. I could’ve been like, “God! Like, our marketing, or our logo, or our culture,” like you honed in on a very particular aspect of the business. Is that the thing that’s sort of zoomed to the top of your list in your mind or—or?

CL I don’t know that it zoomed to the top of the list, it was just like, “Ok, let’s—let’s just do this already. Like, let’s rip this bandaid, rather than be complaining about these things,” and it’s just like me and Gina, it’s like, you know, the rest of the company, things filter up to the top. And it’s like, no, we need to make sure—

RZ Tools! And how we worked and—and—

GT We were about to hit 100 employees, and the way that we worked and the tools that we used to work were not serving us. So that was a huge risk to the business. I mean it—Naturally, at the top of Chris’s list, once he presented it to me I was like, “Yes, we should do this,” I knew he was driving it. You know, I was thinking about marketing and branding culture. Culture is always at the top—

CL Yes. 

[22:50]

GT—of my list, right? Because it’s so important just for our team and for our clients and all that. And strat. I mean strat was, you know, obviously—

CL For both of us. Yeah.

GT—at the top of the list. Cuz we were transitioning a new head of digital strategy cuz we came out of those roles.

RZ Tie that to the theatre degree [Chris laughs] from the first slide. I’m trying to piece it together. 

CL My point was like, I’m not some business savant who knows exactly what we should be [Gina laughing] doing, I just care about great software and making the experience great for all of our employees, and so how do we—

RZ You’re just saying, “Look, this is just my judgement call. This is not an MBA talking.” 

CL Exactly. 

RZ I got it. Ok! Gina, your turn. 

GT I mean, digital strategy, the digital strategy group, this was less like, “Lemme change the thing that Rich and Paul had,” but as a result of this transition we were building out our strat group. We were building out our strat group anyway.

RZ Gina, take a minute, tell everyone, like, digital strategy is a hell of a term. What does digital strategy mean at Postlight and what were you attacking? 

GT Digital strategy is a cornerstone of our business, right? Like, we’ve repositioned ourselves in the market, I mean, you know, this happened a while ago, as a strategic partner to our clients. As a partner who can say—can not only kind of fulfill your order but to say, “What issues does your business have? What problems are you facing? What goals are you going after? Ok, digital’s gonna be a huge part of that because it’s 2021 and here’s how digital should be a part of that, right?” So giving that guidance, giving that advice, you know, really internalizing business problems. So the digital strategy group talks to prospects, monitors active engagements with our current clients, the health of that relationship, the health of the deliverables, the quality of the deliverables. If there are other, you know, new opportunities for us to partner in new and different ways. 

RZ Yup. 

[24:30]

GT And also, they’re in charge of, you know, essentially the Postlight brand. The way that we speak to the world at large, not just our prospects and current engagements. So, it’s a huge amount of responsibility. They’re the frontline of, you know, the services we provide. And we have a fantastic new head of digital strategy, Michael Shane. He actually did a great episode of this podcast, talking about what a strategist is and what strat is. You know, he was building out his team, it was a new—it was a kind of a—I wouldn’t say a baby group, I’d say like a toddler to middle schooler kinda group. And now I’d say they’re kind of in high school.

RZ So you felt that, “We gotta beef-up this group. We need more firepower in that group,” was that like top of mind when you were comin’ in?

GT Not just more firepower but part of it was, like, underst—Like, you and Paul were strat for so many years and there was so much happening—

RZ Yeah. 

GT And between the two of you that no one else was exposed to, right? You brought us in and then you were externalizing to us and we were running strat and now we had to do that with Michael and his team, right? And not just knowledge transfer but also just like there was an evolution that had to happen at 100 plus employees that didn’t have to happen when we were 30 or 40 employees and making sure that we were not just being reactive, that we’re being proactive. This is a work in progress, right? And Chris and I are still really involved there. Again, this was like part of the letting go and empowering our other leaders inside the org [yeah] to do the things that were really inside both of your brains for so long. 

CL I mean, I think another change that we made, looking back, is talking more about the vision and the mandates for the company, as opposed to the tactics, like what we’re doing. And we probably didn’t have to do it when we were 35 people but as we crossed 100, it’s like, “We need to chart the path here. Where are we going?” And that’s really hard for an agency, actually, because it’s not—there is no central product that is our mission. Paul, for a long time you said craft is our mission and I think that’s still a big part of our story. But the vision statement that Gina and I crafted is really around our clients. We wanna impact lasting change for our clients. And we want every single person at the company to internalize that like, that’s why we’re doing what we’re doing and mandate is to grow around that vision. 

RZ I wanna shift gears a bit and talk about how—like this wouldn’t have happened. I mean, Paul and I, this was ultimately Paul and my call—I mean, let’s say it out loud. We don’t have a board. There’s other partners but this was a decision that Paul and I made together. One of the reasons we felt good about making it was how you work together, the two of you work together. Obviously we’re outside lookin’ in but the dynamic is remarkably smooth, almost scary smooth. You ever see, like, that marriage where everything is too perfect [Gina laughs] and everyone is too nice? [Gina laughing] Which means it’s about to burst into flames any minute! But I don’t think—

GT That’s your paranoia, Rich [Chris laughs]

[27:19]

RZ Yeah, [chuckling] here’s my paranoia again! But, I guess, talk about that. Like, how did you guys sit down and say, “Alright, I’ll take this side of the house, you take that side of the house,” and that working dynamic. We just learned today that you guys make PowerPoints for each other. Which is sweet and cute. But talk about the dynamic and throw us a morsel, I mean, there must have been an ug—do you ever have a meeting where you’re like, “You know what I’m done.” And you hang up. [Gina chuckling] That happen yet?

GT Not yet! 

RZ No? I’ve hung up on Paul like 60 times. 

CL Not yet. 

RZ Come on guys. 

PF We should tell the company and the world that you are joking there. Like, it is the same, I don’t—I think I’ve had—No, we’ve had like four like showstopper conversations in five or six years. 

RZ Which, by the way, in the world of partnerships—and that could be too brothers owning a bodega, it is the exception. I mean, it really is the exception. 

PF One of the jokes I make but it’s also serious is if you and I had done this earlier in life, if we had done this in our early thirties, it wouldn’t have worked. Like there’s a point where you get a little older and you’re like, “I need people who can do those things. I can’t do those myself. And if I try it’s not as good.” 

RZ Yeah, yeah, yeah. I think you might be right there. 

PF There’s an element of that, like that’s a part of adulthood that really works. 

RZ Frame it as advice: I mean, a lot of people struggle in partnerships. What makes it work? 

CL I feel like the things that are coming to mind are like very cliche but like, mutual respect. Like, you have to look at the person at the other side of the table and feel like, “Yes, they are smart and good and making the right calls,” making the calls that you would make. Like, Gina and I agree on like 97% of the things that we would do. You know, individually. And then the three percent that we disagree about, I feel like we’re very quick to either come to a resolution or be like, “This isn’t what I think we should do but I’m gonna go with it.” 

[29:14]

GT It’s always surprising. We’re always, like, surprised when there’s a disagreement. It’s funny, you know, Chris and I have worked together at Postlight for years. I reported to you at one point, Christ. I think in the very beginning, when I first joined, I remember you giving me a performance review at some point. Like very early, like 2016. 

PF Hah! 

GT But then we were in kinda different parts of the company, we didn’t inter—Our workstreams didn’t require us to interact a lot, and then we started working on the MTA project together and that’s when I really, really started to like, see into Chris’s—the way that he thinks about product; the way that he handles tricky client conversations; the way that he pushes forward platforms. And I just—like this tremendous amount of respect and admiration grew there. Chris doesn’t get hot under the collar or react in an emotional way in meetings. There’s something I struggle with [laughs] so I’ve learned a lot from him that way and I’ve been in a lot of business partnerships throughout my career, different kinds of business partnerships, and this one is very, very healthy and positive. I think that we’re very upfront with one another. At one point we had a conversation where Chris said to me—I don’t know maybe it was a couple months ago or a few weeks ago—he said to me, “You know, I feel really accountable to you.” And I feel the same way: I feel very accountable to Chris, like as—as his partner. So it’s very healthy. I mean, I’m sure that we’re gonna have a blowout at some point, I don’t know. But [chuckling] it hasn’t—it hasn’t happened! 

RZ No, that was a joke before. 

CL Start the countdown! But, this bit about working together, that is real. Like, I think, Gina and I both really care about the work and so getting to work with the MTA—MTA was an amazing project—

GT Yeah. 

CL—great client but, you know, you’re on the frontline, you’re in the trenches together. So you’re seeing how do you motivate a team. I was watching Gina, like, build relationships with our client stakeholders and seeing firsthand like, “Oh! She is exceptional at this! And she knows how to position this team and, frankly, this company in a really amazing way as we think about, you know, what’s ahead.” In the context of the MTA, it was for Mercury, this project that we were working on. But it was like almost a direct line to, ok, as we took over digital strategy, how do we think about, you know, positioning Postlight in the same way? So doing the work together and finding your, you know, your vibes through that, that’s a great bit of advice.

RZ I mean, it was—it was a key driver. When Paul and I would talk and, you know, this wasn’t a trivial decision, it took over a year of a lot of consideration. The dynamic on that project and the way you guys worked together was definitely in a lot of the conversation. Paul, you were gonna ask. 

[31:45]

PF Well, I mean, here we are talking about what happened and how it works, like now is a chance: what do you see coming? You’re working together, you’re about to get into your second six months, you’re gonna be headed towards a year, like, what—what’s gonna happen in your relationship and in how you’re running Postlight? You’re kinda—you truly are settled into the job. Like, I mean, it really is a—our parts of managing and mentoring and leading feel increasingly done, feels like you’ve just—you’ve got the reins. So what now? How are you gonna scale this thing? Whatcha gonna do? 

GT I feel like we—we spent our first, you know, half of the year, first six months, really, like, navigating the teams with this change and turning inward and making sure that we were efficient, that we had good processes, and good tools, and we established our senior leadership team. For me, you know, 2022 is turning outward and spending more time with our clients and writing more and getting out there and speaking more and being on the podcast more. Like, we have an extraordinary group of leaders in our senior leadership team who work with us and they’ve all found their footing, and they’ve understood how this—you know, our working dynamic, and how this goes, and so I’m really looking forward to that. I’m looking forward to building relationships and representing the company externally. 

CL Yeah. We also have to continue to invest in—with scaling, comes the challenges like onboarding and making projects run efficiently. We have this framework called CORE which we’ve talked about on the podcast before. There’s like a new evolution of CORE that is ahead of us, which is how do we customize the framework to meet the stage of the project that we’re in, right? We’re taking on newer, different kinds of work, some of our work is purely strategy now. Which is like, “Hey, we have this big challenge in front of us, tell us what to do with it.” As opposed to, “Build us a platform.” Or maybe it’s one step before, “Build us a platform.” And we’re really leaning into that, and that means that checking in on that kind of work looks a little bit different. In the same way, when we’re working on, you know, we’re taking on more and more long-term maintenance projects where we are supporting platforms that have been in the wild for two, five, ten years. And that’s interesting and exciting but it’s a different kind of challenge. So how do we orient and build teams that are really motivated by that? And, likewise, how do we check in on them? And what are the success metrics around them? 

PF The altitude at which you’re operating, right? Like, that’s—that’s the big change is that you no longer can do these things directly yourself. Up until you took this role, you were able to do things—you could write a document, send an email, ask to sit down with somebody, tell somebody something, and now it’s like this art of suggestion and broad strategic goals and seeing how people report back. I mean that’s great. That’s wonderful. It’s complicated though. I missed so much in the role of CEO. I really missed being able to make and do things, it’s so much faster

[34:34]

GT The first six weeks Chris and I kept being like, “Oh, I’m gonna do this thing,” and then the other one would say to one another, “Who should be doing this thing? Should you be doing this thing?” And it was this horrible moment where you’re like, “You’re right—” 

CL You can’t do it [laughs]. 

GT—“I shouldn’t do this thing, now I have to—” And then you just—you give it to somebody else and then you’re just like, [holding breath, high-pitched:] “I hope that goes well.” [Everyone laughs

PF Yeah. 

CL Exactly. 

GT And then it does! 

RZ So, I wanna close it with a question for the both of you: is Postlight hiring?

GT We are so hiring. 

CL Full steam ahead on hiring. 

RZ So, so hiring.

GT postlight.com/careers, you should go there in your web browser right now. postlight.com/careers

PF I’m goin’! I’m goin’ to the website. It says, “Yes, we’re hiring.” 

CL Great product managers, great product designers, incredible engineers, we want ‘em all!

PF Content strategist contract. We’re looking for directors of engineering. We’re looking for lead designers. Boy, we’re—this place is growing! What an exciting firm. 

CL You know, it’s funny, we’ve talked to some people who applied and got hired and then said to us, after the fact, “I’m kind of amazed cuz I never thought that I would make it at a place like Postlight.” And so it’s worth saying to people: we do want all experience levels. And we want this to be a place where people can grow their careers. And so if you’re a little more junior or a little earlier in your career, don’t let that mean that you can’t reach out because we wanna talk to you and we’ll figure out how to support you and bring you to that next level along with us. 

GT That’s right, you should apply. 

[35:58]

PF If you have a bias towards just getting stuff done, we can work with the rest of it. 

RZ Guys, I wanna end this with a compliment. You guys have been—I mean it’s exceeded what Paul and I expected in terms of [music fades in] steadying the ship, providing a place that cares about people growing their careers, and just taking it to a mature level. And that’s so necessary, we’re 120 and counting now. You guys have done a great job!

GT Honestly, you both get credit for making a great decision!

PF There you go [Paul, Rich, and Chris laugh]. 

GT And this has been a blast! And I just—you put in a tremendous amount of trust in both of us, and it means so much to us, and even if my face falls in a meeting because [Paul laughing] you’re giving me feedback [Rich laughing], I will always welcome your—

RZ Oh, here we go. 

GT—a dvi—I mean, your advice and counsel has been key and will continue to be so. 

PF Just like we welcome feedback to hello@postlight.com.

GT Exactly! [Rich laughing] Send us a note at hello@postlight.com

RZ Well, I’m excited to see what happens in 2022. To all our wonderful listeners, you’re gonna hear more of Chris, Gina, and others at Postlight on this podcast next year. Have a wonderful, safe holiday, and see you on the other side. 

GT Happy holidays, everyone. 

CL Happy holidays. 

PF hello@postlight.com. Also, happy holidays! [Chris chuckles] Bye!

CL Bye! [Music continues for seven seconds, fades out to end.]