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Episode 141 October 30, 2018 | 39min

Postlight Is Three

We talk about who we are and how we lead.

Show Notes

Don’t Add Bullshit To The World: In recent episodes you’ve heard our guests talk about scalingethicsdesign, and engineering — now it’s time to hear from Postlight’s partners and leaders. We discuss the diverse backgrounds of our leadership team, how have their roles have changed over time, and how we come together to make good software while shipping great products. This episode is also the debut of Paul’s new, deeper voice, which Gina calls “a massage for your ears.”

Paul Ford Uh your weren’t a Comp Sci major though, were you?

Chris Losacco I was—I was a Comp Sci major.

PF Oh! Ok, ok.

CL Yeah, double major.

PF What was the other major?

CL Theater.

PF The—this just always is amazing to me [laughter] [music fades in, plays alone for 18 seconds, ramps down]. I’m Paul Ford, co-founder and CEO of Postlight.

Rich Ziade I’m Rich Ziade, co-founder and President of Postlight.

PF Rich, today is not about us.

RZ No, it’s not. Is it?

PF And, in fact, people know who we are. They know what we do if they listen to this podcast.

RZ Yeah.

PF And let’s just . . . stop talking and start listening [music fades out].

RZ Yes.

CL Hi! My name is Chris Losacco. I am a managing partner and the Head of Product at Postlight.

RZ Welcome, Chris.

CL Hi guys.

RZ I’ve been working with Chris for . . . almost 14 years now.

CL Yeah.

RZ Chris is an immensely talented product lead. And we care about product management a lot. Chris is able to do it at a scale that very few people can.

PF Well, wait, can—Chris can you—

CL Thank you.

[1:08]

PF Can you define the job? Can you say what a product manager does?

CL Product manager is the—the champion of the thing. They want it to be the right solution for whatever problem is out there so they are the—the ones fighting for the users of the app and making sure that it gets there on time. Working with design and engineering and everyone else to get it across the finish line. And get it into the hands of the people.

RZ Chris, draw a picture of the product management team at Postlight. By the way, Paul, a very talented group.

CL So we’ve got a great collection of PMs who are v—extremely well rounded. We’ve got, you know, some folks are uh more technical than others, some folks have a—a design bent, but everyone’s kinda has a baseline, you know, level of knowledge about just creating software at every level and we’ve got people who are good on the ground, who know how to drive towards shipping and getting something across the goal line. It’s people who know how to put the designer and engineer together and get a list of stuff, bullet it out, and hit the ground running, and then take it across the finish line.

PF One of the things that really defines you to me is that you have an instinctual horror of things that are of low quality. Like it just like [hmm]—you can’t put one over on Chris. I’ve seen it—I’ve seen—everyone’s tried, including us. Like you’re just like, “I think we can just compromise and get this out—”

RZ “Just, yeah—”

PF “And the face won’t—”

RZ “Duct tape it!”

PF “Face won’t change.” Where does that come from cuz you’re not like a—you’re not like an angry person but there’s this thing—

CL No—

PF—where you’re just like—

CL There’s a lot of bad software out in the world [yeah] and we just don’t need to be adding to it. Like let’s make—if we’re gonna make stuff, let’s make good things.

[2:53]

PF That’s true. I have a little maxim that I came up when I was trying to figure how I was gonna work and it’s just don’t add bullshit to the world.

CL Yeah! That’s right.

PF So . . . what—what is good software?

CL I mean good software is something that is at the very least not a pain to use, it doesn’t add friction and frustration to your life. It’s something that is good and at its best it’s uh joyful to use. It—it’s something you look forward to uh, you know, interacting with and—and getting to experience.

RZ This is interesting cuz uh we’re talking about product but what you’re really talking about are the motivations and like the inspirations behind good design.

CL Absolutely! I think good design is critical to good product work.

RZ Yeah, and a good product manager cares deeply about it and a really great product manager has taste.

PF Aesthetics become part of everything, like they also are part [mm] of the engineering.

CL Yes!

PF You know it can’t be a big mess cuz then you can’t build something beautiful on top of it.

CL That’s right.

PF When you’re building things, how do you get the engineers and the designers to kind of find a peaceful way forward?

CL The thing that we’ve built here, I think, is we’ve got people on both sides of the coin who respect the other discipline immensely. So you’ve got engineers who really care about design and vice versa designers who are really interested in engineering. And so getting them to play nicely together is not really a challenge, like you get that outta the box. I think in the industry you need design to appreciate that engineering is what’s bringing their design to life and you need engineering to realize that design is driving the product forward, design is driving the experience forward. So you just want there to be mutual sort of respect and appreciation for the other side of the table.

[4:36]

RZ Product management is weird cuz you’re sort of like the interim boss. Like you’re really pretty much gonna set the agenda and frankly the day’s work and days and and weeks of work for a bunch of people.

CL Yeah, that’s right!

PF Mm hmm.

RZ When things aren’t feeling right or you’re sending someone back in to do it again [yeah] there’s a couple of ways to do it. Now, Chris has a skill that I don’t have where rather than saying, “That’s not gonna work,” or gettin’ riled up, he just kinda keeps sending you back in. And that’s hard.

PF Look, I heard the answer in the—the first thing we talked about which is that you’re an advocate for the user.

RZ Yeah.

CL Yeah that’s a huge piece of it.

PF People need to get where the user’s gonna be.

RZ Yeah.

CL You can’t talk about the how. You have to talk about the what. Like the what you’re doing. I think it’s hard when you send people back in and say, “You did this wrong, you have to do it this way.” But instead if you say, “Look: we’re trying to get across this line and we’re just not across it yet, like, we need to give it another shot. We need to go that extra ten, 20, 30 percent, whatever it is,” people are much more likely to say, “I see where you’re going, we’re aligned in the same way. I’m gonna go give it another, you know, another round.”

RZ Even though you may be the advocate for the product as you’re describing and an advocate for the user, very often there is a business that is—has asked for the thing [yup] and you have been assigned to make sure the thing gets out there. Talk a little bit about balancing relationship and execution.

CL I mean how I like to approach it and how the team approaches it is translating what we’re hearing from the key stakeholders on the client side into how it maps to the users of the product, and how we can achieve what they’re after on the business side with real goals about what somebody wants to achieve, how somebody wants to use it, that kind of thing [yeah, yeah]. We wanna tie it back to . . . how are people actually using this thing? What are we not doing that you’re after? And how can we get at that problem rather than just responding to needs?

[6:43]

RZ Yup. Did you think you could be a product manager even coming out of school? Did you even know the definition of the title?

CL No. No.

RZ What’s the—for someone that’s thinking about jumping into this territory, cuz we have listeners that are engineers and designers and frankly other types of managers. Starting point.

CL Start with what a user cares about. And how do you conceptualize how you’re putting a product together that’s gonna be in the hands of real people actually using it. Start there. And then kind of layer in, you know, architecture and the other engineering pieces, and knowing what’s out there, and how to kinda pull the pieces together cuz those are important parts of it too. But I think the basis has to be: what are the people who are using the—the piece of software doing and how do you [music fades in] orient yourself and the team around that? [Music ramps up and plays alone for eight seconds, ramps down].

Meredith Franzese My name is Meredith Franzese. I’m a managing partner [music fades out], uh Head of Operations at Postlight.

RZ You would think based on how we described Postlight that it’s just a bunch of people having a good time in a garage.

PF Yeah, you might think that [Meredith chuckles].

RZ You really would think that. Like, “Hey guys! We’re passing around the seamless web phone!”

PF This is a business.

RZ It’s a business and we’ve [chuckles] gotten bigger and boy, would the shit unravel if we didn’t have somebody taking care of the gears that make it run, and beyond just what we deliver for clients.

PF There’s a reason this machine rolls along.

RZ Yeah [laughs and Meredith laughs]. I—I can draw Meredith’s face when I say, “Mer, I got an idea!” [Laughs]

MF It’s uzh—it’s usually a good idea [Rich laughs, Meredith chuckles]. It’s just as long as we have enough time to get it done.

[8:29]

RZ Give us your professional path, story, in like three minutes.

MF I—I mean I like—I like operations. I’ve always worked in either new business initiatives in large companies or early stage companies. I think that there is one thing that I’m good at which is taking—Rich has an idea [chuckles] and—or anyone has an idea and pulling it together into something that actually, you know, happens.

RZ Execution is what you’re talking about.

MF Uh yeah I like execution and I like execution though when you start at the messy part.

PF So . . . Rich comes in and says, “We need to open a—well, office in Lebanon,” is a good example. I was going to say hot dog stand—

RZ I mean that was a big project, right?

PF Right.

RZ I mean that was—

PF So these are—these are the sorta things that fall into your world and a lot of them are very abstract like where do you start?

MF Usually with what’s the goal and objective [mm hmm] and—and then that’s usually closely followed by when does this need to get done? Because just as a for instance if we wanna do an event around . . . the release of something and we’ve got three months to figure it out or three weeks, it—it immediately becomes a different scope of work.

RZ And just to—just to highlight: we’re saying event. Many people who listen to this have never been to our events. Our events are not like, “Let’s order some pizza.” They’re—they’re usually productions to some extent.

PF No, they’re catered, they’re well produced, they’re recorded if it’s appropriate—

RZ We have to communicate out with our guests and there’s a lot going on here.

MF Yeah, I mean marketing for us is tough because—

RZ It’s marketing—

[10:03]

MF Well yeah and we—we make a lot of cool things that we can’t talk about. So we have to constantly be looking for ways to connect with the community that often isn’t tied to the work that we’re doing 90 percent of the time cuz we can’t really talk about it.

PF What’s your goal as the person who runs ops inside of Postlight?

MF A lot of times when we think about operations as the team, we think Postlight is our client. It’s like we’re in client services here at Postlight and our job is tied to what are the objectives of our client, Postlight, and that will sometimes that’s really heavy into growth of people; other times that’s in turning up the signal around how Poslight’s performing; sometimes that’s doing taxes [laughs], uh but we are like you would run a client engagement, we’re constantly taking the temperature and looking at the long term goals of—of our client.

PF Ok so how—you have a team [mm hmm]. Talk a little bit about the team, how it’s made up to get all these things done.

MF Yeah, so we have individuals that are really experts at the different parts of operations. So we’ve got a really great Director of Human Resources—

PF That’s our friend Christine Morse.

MF Yes! We have two people on the marketing team that drive both the strategy and also the design which has been a new addition which has been great. And then we have two people that are really great utility players that can help fill in.

PF So, we’re on this podcast, we talk about design, engineering, product, we rarely talk about ops but like what is it like running a group that isn’t the star of the show in the way that those other three things are going to be the star of the show for us to sell?

MF Yeah, you have to be ok being behind the scenes, like behind the scenes with the headphones on, because you’re not out on the front of the stage if you’re in operations in most cases, and I think the big goal or part of the operations team that I think I’m most proud of and the team is most proud of is the ability that we’ve had to build the culture of Postlight where people feel like they’re part of Postlight even though everyone’s on really different work projects, different pacing, different clients that they’re interacting with. And I think that that’s tied to both our commitment to hiring people that love their craft and excel at their craft, and, you know, sharing culture. Where we’ve been able to have people feel connected to Postlight as a bigger entity even if their day in and day out is, you know, at one of our client’s offices.

[12:26]

PF So enabling that becomes your job, right?

MF Mm hmm. Though you—you—you don’t give yourself enough credit. I mean part of what works here as the culture, I think, is that we allow people to have a life outside of Postlight and I think that comes actually from the top down. Like having a good work-life balance, encouraging people to have interests outside of just their job at Postlight [mm hmm], is—is been something that is really starts with—with both of you and is something that has come throughout the org. And the other part is just a commitment to the craft. And we’ve said that from day one at Postlight. We—we ship products and we care about our work and that is really in any position you are in Postlight I think that that’s a true statement you can make about someone here.

PF I mean that is real. We do obsess a little bit about quality [Meredith laughs] cuz—No but I mean and that’s—if the quality slips, the agency goes away [yeah]. That’s—I’ve seen it happen.

RZ I mean I think it’s been one of the big successes. Ops when it succeeds is invisible.

MF Mm hmm.

RZ Alright?

PF Yeah.

RZ To your point—

MF You only—

PF Like a product but—

RZ Right.

PF But yes.

RZ It’s like—

MF You only really see—notice operations when it’s failing.

PF Mm hmm.

MF When you’re like—

RZ Yeah.

MF “Why isn’t the AC working in the office?” You’re like, “It was working the other [laughing] 300 days.”

[13:32]

RZ [Laughs] “Call ops!”

MF Right. Exactly. When something falls apart is when you realize that the machine has, you know, has—has a break.

PF It was very hard for me to ask at one point, I was like, “I think we have to fix a shelf in the toilet.” [Meredith laughs] You know it was just sort of like it was in the early days. I’m like, “I don’t know even know how—I’ll get a screwdriver and do it.”

MF And it’s—it’s broken several times, I mean we’ve learned a lot, right? Recruiting was hard at—at different points and we had to really figure out how do we maintain the quality but also accelerate based on our growth needs? And that’s been—you know, fixing those things has been a team effort.

PF You know the way I’d articulate it is you start and stop a lot when you’re getting the company going [mm hmm]. Like, “Ok, well we can stop recruiting for a minute,” and now what we have are just continual processes. Sometimes there’s more gas in the tank than others [mm hmm] but I don’t—we haven’t stopped recruiting in forever now, right?

RZ Yeah.

PF Like we just sort of keep going.

MF What’s important with operations is you can never take your fingers off the pulse [yeah] because just when everything is smooth and working well, like something’s gonna change and growth, of course, is hard, and growing when it comes to operations in our business is how do you—how do you scale people? How do you scale a Postlight brand and what we stand for [music fades in] without becoming insert big generic agency here? [Music ramps up, plays alone for six seconds, ramps down].

Matthew Quintanilla Hi my name is Matt Quintanilla. I’m a partner and Director of Product Design [music fades out] here at Postlight.

RZ Welcome, Matt. Little origin story: I’ve been working with Matt longer than Postlight’s been alive.

PF How did you find Richard Ziade?

[15:04]

MQ I applied for Arc90 which was the previous agency that we worked together for.

RZ Other side of the—the story here: you know Matt was—was interesting.

PF Still is!

RZ He’s still a very interesting person. So, Paul, at Arc90 [uh huh], we had a weird requirement: weird, weird job rec. The designers had to code. They had to be able to code.

PF That’s cool as long as you’re willing to hire from a pool of—

RZ 11 [laughs].

PF 150 designers in—in America. Um so somehow—well this is good though cuz the designers who could code are gonna find you cuz no one else cared.

RZ [Laughs boisterously] This is true or they didn’t know they had us.

PF So Matt that was you, you knew how to hack stuff together as well as make it—make it look really good.

MQ Correct. I mean I really sort of cut my teeth on learning design first and really thinking that through and just kind of using uh web dev as—as the hobby uh [mm hmm] to make myself more flexible, particularly back then I was I mean I had studied journalism, I was thinking about, you know, where am I gonna end up?

PF Sure. Keep your options open.

MQ For sure. And so, you know, at a place like Arc90 that was—that was very much at the core of how we thought about everything is like how do we build what we’re doing? How do we ship this? And I think that that really influenced kind of how I approach, you know, what we talk about design systems today. Like thinking through every—every module as a piece of a larger, you know, from the atom level to the molecule to the actual organism. Like it [stammers] cuts all the way through.

RZ We’ve—we’ve tossed around design systems a couple of times and it’s a word that gets tossed around these days uh first off it sounds heavy and intense and fancy which is cool. Define it.

MQ Design systems for—for me is about creating a common language, is about creating a system of not rules but a framework to really think and piece together what needs to be built.

PF Mm hmm.

[16:52]

MQ And—and without that, you know, it really does become a—a much more subjective situation. I mean is—is inherently subjective in a lot of ways and this isn’t about creating a barrier to design but instead is to—to really open up the idea that it should share a language just as with writing or—or sort of having a style book for writers is important, it’s important for designers as well. And particularly when we think about the interaction of product design versus just straight up design or—or sort of any other creative pursuit uh attached to it, it—it really is about defining that structure and being able to bend it.

RZ Yeah. Tell us a little bit about the team.

MQ When I talk about Postlight I say, “We’re an agency that positions ourself at the nexus of engineering and design,” and I think that that’s true all the way to every individual member of our design team. We really have crafted a group of individuals that come from diverse backgrounds. That is our strength as a team and really understanding that because we think about product as being the entirety of how something functions, how something works, and—and how it’s designed.

RZ Matt, talk to that person for a second uh who is in design and we talked before about how it’s this kind of big huge landscape um and sort of the strain of design that, I think, we consider success at Postlight—

PF Yeah, what’s gonna make them successful?

RZ Yeah, and—and where can they go? And how should they think about learning in advance?

MQ So when I talk to—to people about coming onto the design team, I really stress that this is a place where there’s a lot of autonomy, there’s a lot of expectation around leadership. Um that person really needs to carry the room in talking with clients, talking with the internal team, and really shape the conversation around design. I’m a Director here at Postlight but I’m not the Creative Director and we don’t have that distinction here. It’s important because it—it really does allow people to come in and—and understand what needs to be solved and—and execute on that from top to bottom. We—we wear a lot of hats here. That’s—that’s user research to wire frames to UI to showing that clients to getting feedback. It’s the whole gamut of design.

PF So you’re—you’re gonna be part of a small team that is—like not the overall design team but [stammers] an individual product team. You’re gonna be on one or two teams at once and you’re gonna be responsible for the whole product as a designer.

[19:10]

MQ Absolutely.

PF Ok.

MQ There’s a lot of support though for those designer. We, as a group, focus our conversations around design in—in our design reviews, around getting just really impactful designer to designer feedback. Uh we do it ad hoc all the time. “I need 20 minutes and a white board. Can we jump in here? Like I need to talk some stuff out.” So you’re not alone. You’re not siloed here but there is a—a very big opportunity for people who want to really leap straight into product design and sort of owning that autonomy.

PF I gotta imagine as Director of Design that a lot of your job is telling people, “Not yet.” [Laughs] “Keep going.” How—how do you do that? Over and over again and still cuz your team likes you. They really do. You’ve noticed this, Rich?

RZ I imagine it’s hard cuz it’s not about, you know, engineering success is often quantitative in—in various ways—

PF Yeah it’s like—

RZ Like how productive are you? The, you know, how stable is your code? And how tight is your code? But design, man, like—People, first off, it’s—it’s expression. As functional as it can be, or is aiming to be, it is still expression and you’re still talking to something—

PF Oh whenever anybody tries to quantify it they just ruin everything good about it. I mean it’s gotta have that spark.

RZ And you will invoke emotion. I mean there’s no doubt about it. So yeah talk about feedback and critique.

MQ There is a strategic aspect of the design that we do, particularly here at Postlight, that I think, you know, measuring that and saying, you know, “Are—are we meeting the goals? Is the client, you know, feeling what we’re doing? Can we measure that?” That’s definitely part of it but you’re—you’re right about the emotional like everybody sort of thinks they’re a designer, clients included, and I think that there’s no shortage of opinions around what is a very subjective field. It goes beyond just like, “I don’t like this blue,” to, you know, “Is this really the right vibe? Like are we feeling it?” Like that’s [Rich chuckles]—there’s a lot of voices around the room around that sort of stuff and so as a director I feel like my role is to prompt the question more. Did we think this through? What else could we have done? How—how further can we take this? It’s about making sure that everybody starts framing the questions, is able to zoom in and out of the here’s the micro of this page but what’s the macro of the entire system? Of the entire solution? How—how do you encourage that sort of conversation and—and bump it beyond just what’s on screen and what we’re showing to the client?

[21:34]

PF It’s hard, right? I mean making things [absolutely] you—you are able to find success, you know how to do it right! I’m gonna do it! And actually help empowering people, you never know if you did a good job or not. Maybe 20 years from now they’ll be like, “ I really learned a lot from you, Matt. Thank you so much.” But today, they—uh ok. Ok. [Rich chuckles] That’s humans. Humans are like that.

MQ Absolutely.

PF Alright so you’re growing this team and so people should get in touch.

MQ 100 percent.

PF Ok so now you know who you’ll be working with and the kind of thinking that happens in Postlight design.

RZ Beautiful.

PF So, time [music fades in] to send that resume, people.

RZ Thank you, Matt.

MQ Thank you.

PF Thank you [music plays alone for ten seconds, ramps down then fades out].

Jeremy Mack Hi, my name is Jeremy Mack. I am a partner and Director of Engineering at Postlight.

RZ Ok. So, before we dive in, J. Mack, about engineering at Postlight. Tell us a little bit about you . . . Uh how’d—just give me the . . . rip through your resume in like 300 seconds.

JM I started out at college in uh Ohio uh as a Cyber Warrior working the Air Force. I left from there after about three years and went over to another air force contractor. So uh I—I ended up doing a little bit more software development there and kinda got into some web development stuff and along the way ended up going to some meetups in Dayton and found a uh company there, an agency, that was doing some really cool web work. About five years out of school I started doing agency work there, kinda taking clients and shipping a bunch of different pieces of software from freezer cooking—uh which was uh an interesting experience of learning how to cook to build software for cooking.

RZ Wh—

JM Um—

RZ What? [Laughs]

[23:26]

JM Yeah. Yeah.

RZ Very cool. Um now at this point, I mean, you’re walking us through your career, and you’re gettin’ pretty close to you and I working together [mm hmm]. You weren’t really managing people yet, if I’m not mistaken.

JM Yeah I was more of a kind of mentorship like I’m the senior on the team and like on the project and I’m helping people [right] figure out where they’re going or maybe running a meetup from time to time, giving a talk at a conference, but yeah [right] definitely not directly managing any engineers.

RZ Right. So, your sort of ascent into a leadership role happened pretty quickly and one of the things that’s impressed me and Paul is how you kind of embraced it cuz engineering to management is not a straight line.

JM It—it was an interesting journey for sure. I—you start your career hacking software and figuring out how viruses and things like that work and then you’re kinda some of the only developer—you know maybe the one developer on a large software project, you get kind of an ego and you start to believe that, you know, you know how to write software best and the other people around you aren’t that great at what they—they’re doing. And the first thing I had to do was develop an appreciation for what other people were capable of, and that kind of uh has just continued to evolve since then—that I’ve trusted more and more people taking over the day to day of writing code on the projects I’m on and I—I get just as much enjoyment out of seeing what they produce or reviewing the code and talking to them about how they approach the problems. I still try to stay relevant by doing, you know, side projects or the occasion strategic prototype for a client um and that’s a great way to stay—stay modern but I know that my best place is to enable all of the people that we’ve hired that I see as peers and who have far excelled uh away from where even I am capable of developing software, uh just giving them the ability to write code is—is really uh—it’s been an incredible part of my career.

PF Yeah. Talk to us a little bit about your team.

[25:17]

JM We started off with essentially me managing uh the majority of the people on the team when it was a little bit smaller and we quickly realized we needed to have uh more managers and the ability for people to have direct contact with somebody who’s guiding their career at Postlight. So it’s been an important thing for us at Postlight that we have a consistent manager for you who’s an engineer that knows your trade and your story at Postlight and that manager is not overtaxed with a bunch of direct reports. They’ve got maybe four or five reports at most and they have more than enough time to be able to meet with you once a week or once every two weeks if that’s what you prefer. That’s how the team has grown and—and gotten to the size it is and still stayed really healthy. Being able to have the people who manage the other engineers at Postlight report to me about the happiness of each individual person, what interests they have, and maybe what new pieces of tech we should be considering, has just been a really good interaction that’s led us grow to the size we are and not have issues where people feel disconnected from where engineering’s going. We’ve done middle management right that we actually have a layer of people who deeply care about the people they manage and they advocate for them up to me, and I make sure that they’re heard at the highest levels. And uh I’ve seen it time and time again produce long and happy relationships with Postlight with its engineers.

RZ One of the things we kinda take pride in is that we like to people we’re not a fill-in-the-blank shop. We’re a ship that from an engineering perspective really likes to kinda continue and keep looking ahead and focus on craft uh, you know, versus like, “Eh we’re one of the best Java shops in town,” or whatever it be. Nothing—nothing against Java.

JM Yeah. Uh I—I like to think that we stay in the cutting edge without cutting ourselves. That we are capable of exploring experimental new technologies which is where the type of engineer we hire at Postlight really thrives. They wanna take a look at what’s new; what solves the problem they had with the last engagement they were on; makes that no longer an issue that’s even possible. So we enable people to look at those new technologies; to talk about them; to experiment with them; bring them to us; and even pitch them on client work. And we bring it in, you know, carefully and we assess things and we try things out and they—they grow into, you know, what our tech stack is that we go to at Postlight. And the fact that the uh engineering team as a whole is able to affect that direction, that autonomy, that ability to have control over your day to day destiny of what you’re gonna be working with, what tools your gonna be using, appeals to the type of person who finds Postlight interesting as whole. That we give people autonomy and we let them make choices and then talk about how those choices went and then adjust them as necessary over time. I think it’s a very mature two-way relationship that we have with engineering where we expect maturity out of them and [stammers], you know, out of tech choices, and we get it back and we get a lot of good conversation and feedback on—on approaches. I’ve had such wonderful meetings with uh people who are running our different engagements at Postlight where they’re telling me, “Hey, this thing right now isn’t working out. It’s not the most ideal. I’m thinking about changing the direction to this,” and I may have been the person who decided the original direction six months ago but I mean the conversation is always wonderful to have and—and more often than not we end up going the direction that the person on the ground decided because they’re very good at their job.

[28:42]

RZ Uh J. Mack, the team is 20 people. How about we make it bigger?

JM We’re actually taking a large effort to make sure that we reach out to as many people as possible with the job opportunities we have at Postlight. We accept both New York based and remote engineers at Postlight and uh I take pride in saying that we have one of the best uh remote cultures when it comes to engineering. So both our engineers in New York and spread out around the United States are completely in the loop and part of the choices we make. So definitely send in a resume, let’s talk.

RZ Awesome, [email protected] J. Mack, [music fades in] thank you so much for this lovely interview.

PF Exactly. Thank you, J. Mack. [Music ramps up, plays alone for five seconds]. [Paul comes in with a deep, raspy voice] Hey Rich, before we talk to our next um—

RZ You need to explain this, Paul, for the audience.

PF So, I went to a corporate event and I don’t actually drink that much.

RZ Yeah.

PF And I overdid it and yelled a lot in the bar.

RZ Why were you standing on the bar at the corporate event?

PF It doesn’t really matter now, does it?

RZ No, it doesn’t.

PF It is kind of going to be an awkward contrast when this is edited together.

RZ I think I love it.

PF Maybe I’ll just keep this voice.

RZ Uh I kinda like it.

[29:55]

Gina Trapani It’s giving my ears a massage.

PF I feel—

GT Like the bass—it’s so low that I can—

RZ Yeah.

GT—feel the vibration in my ears.

PF Well it’s either this or if I—I try to talk in my regular voice [voice cracking] it does that. [Back to deep, raspy voice] So we’re gonna just go with this.

RZ Yeah.

PF I’m sorry everyone. Alright, so let’s talk to Gina Trapani about her work as um a managing partner . . . at Postlight.

GT Hi! I’m Gina Trapani and I’m a managing partner at Postlight.

PF Gina, your role is a little bit different than many of the other managing partners and directors here. You used to uh manage teams as a Director of Engineering.

GT Yes I did.

PF But now you don’t have a specific portfolio. You’re—you’re just sort of focused on growth of the company.

GT Yup. Internal and external. So I help with sales but I also help—help with some culture stuff.

PF What’s it like not to have a team?

GT A bit different. I mean I think being a manager of a team is a certain kind of mindset and you’re advocating for your people and—but I think, you know, not having a team and thinking about the business as a whole is a shift, for sure.

PF You know, when you had a team it was pretty clear like what you did all day. You—you talked to your people, you’d program, and—and [mm hmm]—and build things, uh sometimes talk to the clients, work with product managers. What do you do all day now?

[31:06]

GT So, my role has shifted really from like—from maker to manager, right? So my work now is meetings. My work is not like get commits and [chuckless] and one-on-ones, it’s more—it’s—it’s higher level and it’s interesting, it’s something that I’ve been figuring out. Like how do I quantify my work product when I spent the day in meetings talking about decisions and strategy, and talking to potential clients, and then sometimes I sit down at my desk and write a proposal or write an internal document like our charter or, you know, what our, you know, titles mean.

PF It’s wei—weird, right? Because success if very abstract.

GT Very abstract.

PF Like it’s sort of is the business growing and overall successful?

GT Yeah. Yeah, like the health—I’m like, you know, my mandate is to, you know, the health of the business, right? But like that’s—that’s very squishy and kind of like invisible, I think, you know, to—to everyone. So, it’s a different way of working and like thinking about, you know, what you’re—whether or not you’re being successful.

PF Are people still coming to you for mentoring and for council and coffee?

GT Yeah, that—that still happens but I think when you—you know when you have a title change and you’re not kind of on the ground with people like the—the dynamic changes a little bit, you know, there’s—there’s a little bit of a different power dynamic. And I’m definitely navigating that. You know, how can I be useful but how can I also be responsible as a leader here?

PF What are the things that surprise you about sales? Like you and I and Rich are out there telling people about this company and asking them for large sums of money.

GT The biggest thing that surprised me and that I’ve learned mostly from Rich like so I had this notion that like you, you know, sign the contract and then the contract dictated the terms of like how the things were done. And the big thing that I’ve learned from Rich is that it’s actually the relationship that drives what happens and that the contract is just a documentation. It’s just an artifact. And of course we have contracts and we enforce them, right? But like the relationship is the thing that matters and it’s an ongoing conversation, and it’s not something that you just set up and go and you’re done. And it’s not, “Eff you. Pay me.” Right? It’s like, “How can I help?” And things change, the statement of work changes, the needs change, sometimes the work is different than you thought it would be, and that’s ok. Like that’s actually not an outlier. That’s a, you know, an expectation. So, that was surprising to me. I thought that I was gonna have a lot more conversations about what the contract says and that [chuckles]—and Rich—this is the thing that I really learned from Rich is that as soon as you’re talking about the contract, like you’ve lost [laughing].

[33:24]

RZ When you’re going back to the terms. Yeah.

GT When you’re going back to the terms, you’re in a bad place. You know? That surprised me.

RZ Yeah. That’s—that’s something to adjust to. It’s oftentimes when we sell and you can attest to this [mm hmm], we kind of have to get them relax about it [yeah]. Cuz they’re like, “Wait, but shouldn’t put this in?” I’m like, “Look: this is gonna change. This is the framework. [Software changes] Software changes.”

PF Well you know I think what’s changed overall in the business, just at least from my perspective over the last, you know, x years, is that . . . the people on the other side of the table actually understand that, they’re not buying a new cabinet or a car. It’s—they’ve built something. They’ve seen where things go wrong—

RZ Mostly understand it.

PF They do and you say like, “Look: there’s gonna be a point in the middle where we don’t know what’s gonna happen.” You know—

GT Right. And there’s like what happens if? And I’m always like, “We’ll talk about it. Let’s talk about it.”

PF Yeah. That’s right.

GT “We’re not here to—you know we’re not robots. Let’s just talk about it.”

PF Some things go away. I think what’s very—it’s hard to—people have a real vision in their head of what’s gonna come out the other side and it’s hard to articulate and get them to buy in that this is gonna be a journey. Like because then—then it—it sounds—then it involves them trusting us a lot.

GT Yes.

PF Because actually like—and this is not cynical. It’s a good reason why you are a face of the company because you’re trustworthy but also it’s an earned trust that you take very seriously.

[34:44]

GT Absolutely and I think that’s even what I mean by a relationship like you’re building like the—the trust factor. Building that trust and saying, “Things are gonna change and we’re gonna talk about it and we’re gonna adjust, and we’re gonna figure it out,” um is—is the most important thing and that’s—I was like, “I’m coming to Postlight and I’m gonna build software.” But it turns out I was coming to Postlight to build trust and relationships.

PF Well but that’s—that’s a big part of getting people their thing.

GT Absolutely.

RZ Can I share another strength of Gina’s?

PF Sure please.

GT Wow.

RZ She’s really good at delivering bad news.

PF Yeah, that’s true. Gina, deliver some bad news for a minute.

RZ Yeah, could you tell us something bad?

PF Hey, Gina, lemme—lemme give you something: it’s gonna—it needs another 30 days and a key person’s about to go on vacation. Tell me what’s gonna happen.

GT You know have you ever seen like a slug? You ever pour salt on a slug like when you were a kid?

PF I’m not a monster.

GT Have you ever seen what happens? The slug just starts—

RZ Savage.

GT—like—it starts like—it’s like twisting.

PF It’s terrible.

GT It’s terr—it’s a horrible—

PF You’re—it’s like burning it with acid. It’s terrible.

GT That’s what I feel like inside when I have to give [Rich laughs] bad news um so [Paul laughs] it’s surprising to me that you think that my delivery of bad news is—is tough. Um so—

[35:50]

RZ Your nervousness and anxiety engenders empathy, right?

GT Exactly.

RZ People are like, “Oh man, you know, she’s feelin’ as bad about this as I’m gonna feel.”

PF “Uh she wanted it.” [Yeah] You wanted it just as much as they do. Yeah, so this is really interesting, Gina, because you’re very—you were very committed as a practitioner and you are very proud of being a practitioner and uh you’re also someone who came here from a very kind of—you were in control. Entrepreneurial. You had everything kind of like in a startup . . . that you managed. And suddenly you’re in this dynamic environment in which you have bosses, you have people reporting, you have then no one reporting. So like how is that transition? And how can people succeed in that transition?

GT I mean I think that the key thing to ask yourself if you’re deciding whether or not you want to move from a individual contributor role to a leadership role is I mean you have to be honest with yourself about whether or not you can be happy in a situation where you’re mostly in meetings and you’re mostly managing other people doing the thing that you normally do. Can—is that a situation that would work for you? But for me the deciding factor that I could have impact at a bigger scale as a leader than I felt that I could as an individual contributor and that was very attractive to me. Um so I wanted to optimize for that even though I don’t love being in meetings and I miss coding everyday. That was an ok trade off and I think that that’s just the base of the trade off.

PF I think you learn more faster too. I mean there’s a certain of stuff that you could’ve learned about engineering with that same amount of time but you were gonna learn more [yeah] about leadership.

GT I mean I also just have this like entrepreneurial streak like I like the idea of like leading and growing businesses. Like I’m very passionate about that. And that’s something I’m really interested in. And I couldn’t keep my nose out of what was going on with the business even when I was an engineer [mm hmm]. Uh so, you know, and some of that is just like following those instincts.

PF Well we’re very glad you’re with us.

GT Glad to be here.

RZ Absolutely [music fades in, ramps up].

PF You know what’s wild? [Sighs] I work with these people a lot, right?

RZ Mm hmm.

[37:49]

PF And they’re dealing with me as CEO.

RZ Mm hmm?

PF And it’s rare that you just say, “Hey, what’s your job again?” And it’s interesting.

RZ It is interesting and it’s interesting to hear them talk about how they think about their job.

PF That’s right to see that perspective because it’s—you see it everyday. You see it acted out. It is a very high performing team. I mean the firm does well [mm hmm] and we’re successful and it’s because of that team. That’s not even a like managing things, like, [insincerely:] “Oh, you know, go team!” [Mm hmm] People who are listening just heard what successful people in this field sound like.

RZ Oh yeah! Oh yeah!

PF And so—but it’s good. It’s—I love to pin people down and be like, you know, “How do you see your job? How do you see what you do?” And that was pretty cool.

RZ Very cool.

PF Well—

RZ I wish somebody would do that with me.

PF [Laughs] Me too [Rich laughs]. I’d love to know what my job—I’d love a job. You know? Just a job [Rich laughs]. “Hey! Paul! Good job today! You did a good job!”

RZ Yeah.

PF Not like, “Thank you. Uh I heard that.” That’s usually what—

RZ “Got it!” [Chuckles]

PF “Got it, ok. I appreciate that you took the time to give me that feedback.” That’s—that’s what we usually get. Alright, well, you know what? It’s time to get back to work.

RZ Have a great week everyone! And happy third birthday, Postlight!

PF [email protected]—you need anything at all. Bye! [Music ramps up, plays alone for four seconds, fades out to end.]