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Synthesizing Ambiguity

with Justin Hughes of Trunk Club
Jun 28, 2017
31
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31
Synthesizing Ambiguity | 100 PM
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Synthesizing Ambiguity | 100 PM

Justin: Hi, I'm Justin Hughes and I'm the Vice President of Product and Design here at Trunk Club.

Suzanne: And we're in Chicago.

Justin: We're in Chicago.

Suzanne: Have you always been in Chicago, by the way?

Justin: I was born and raised here on the southside of Chicago.

Suzanne: You were. Okay. Full disclosure to the audience, we are in the heart of the heart, I think.

Justin: We are. We're River North of Loop here right next to the L.

Suzanne: So if you hear trains and sirens, those are the sounds of Chicago and we're incorporating them for authenticity.

Justin: Right. Matter of fact, I go into the country and I can't sleep without those sounds, so definitely authentic Chicago.

Suzanne: I want to kick off, Justin, by talking a little bit about your path into product management. Something caught my eye in your profile and that is you studied product design and development in school. A lot of the folks that we talk to on the show, they end up applying the product manager label retroactively and say, "Oh, that's what I've been doing for the past 10 years. I just didn't know it." There seems like there was a little more intention for you. Can you talk about that for us?

Justin: Yeah, absolutely. I think don't let the degree fool you. I started off in the same spot. Maybe a part of me always knew that I wanted to be a product manager. I think when I was a kid, I used to keep journals of cool ideas I had and things I wanted to invent. I used to do things like tape together hammers and screwdrivers and say like, "Look at this new product I made." I don't think I knew the path to get to doing that kind of cool job.

I went to college and I studied mechanical engineering because I thought that was actually the path that you went down to become a product developer and designer and quickly found out that wasn't the case. I ran out of money actually at that point in college and didn't know what to do. I had a minor in English literature, which was a saving grace at the end of the day. I just went and I cracked out my English literature degree and I got a job in a call center.

Suzanne: Where all English literature degrees go into.

Justin: Yeah, because there's really no other place. I was like, "What am I going to do with my English literature degree?" I don't know how to get a job and I didn't really want to teach. Working in this call center, I started to make proposals. It's like, "I would do this a little bit differently." Or "I would set this up a little bit differently and try to be a little more efficient."

Eventually I realized there's this job called product management at the company and started shadowing some of the product managers and, "This is really awesome." I was really fortunate to start off in a place at Cars.com that had a rather large product management department, about 80 people or so. I got to start off being an apprentice there and actually working through doing analytical work and breaking down market sizing and doing some wire framing and that kind of stuff.

After I had been there for a few years doing that job as an apprentice product manager, I got a job up here in River North working for an ad tech company and quickly found myself on my own without any real structure or what we defined as the product management process at Cars.com and was really seeking some legitimacy. I'm like, "Wow, I feel like I don't know anything now. It's crazy and I'm constantly questioning every decision I make", which at the time, I didn't realize was just product management.

Was looking around and was really lucky to find that Northwestern here in Chicago has a product management program that's geared towards professionals. What was really awesome about the program is it wasn't really academic. They were really smart to bring in lots of product managers from the across the industry, so I got to study under the guy who invented Tide at P&G.

Suzanne: Wow.

Justin: Really, really smart people.

Suzanne: That's the original. Brand management was the original product management.

Justin: Brand management was the original product management.

Suzanne: Yeah. Wow.

Justin: He was phenomenal. Actually, his course was in how to create a crisis in your organization. It was a phenomenal set of programs. There's actually a couple people I keep in touch with from the program. At first, we didn't feel like we learned a ton from the program. I don't think we knew how to apply a bunch of that knowledge that they taught us there.

Over time, I've really learned, "Wow, there was a lot of really good nuggets that these people left", like little seeds in my brain that hatch over time. I was really blessed to actually go through that program and be able to experience that. At first, it really was about seeking legitimacy for being a product manager. I don't think that I felt like ... there's the train. I didn't feel like it was about going to learn to be a product manager.

Suzanne: Right. Yeah, you said a lot there. Certainly as an instructor and coach of product, I can attest that one of the most challenging things about teaching it is equally the most challenging thing about learning. It's product management is just about learning how to think differently and then the rest is finding ways to assimilate this framework or as I sometimes describe, setting up scaffolding in the middle of an empty field and knowing what scaffolding you need and for what purpose. To go back to Cars.com for a moment, so you're working as a CSR. If I understand your story correctly, you basically started poking holes in the operational processes.

Justin: Yeah.

Suzanne: You were escalating that to management? Were they receptive? They were like, "Oh, great. We love it when new folks come in and tell us how to make the business better"?

Justin: Yeah. I think, yeah, everybody loves when a junior person in customer service starts to tell them how to do their job. I said previously that my English degree was my saving grace. I think I had no idea how to make a proposal, but I thought, "You know what? I'm just going to write a story about how I can see this working a little bit better."

My proposal was really a story of how I would like to do my job and actually, how I saw myself being more efficient when I did these things. I remember my boss at the time really smiling when I gave it to him. He thought, "This is really cool." He's like, "Maybe we can find you a different position and one that's better suited to this kind of skillset."

I think that I've leaned on that English literature degree pretty constantly over the years, even to the point where in this current job, I've even wrote fiction stories about how I want to see the business actually look and pass those on for people to read and actually understand. There's a little bit of an art that I didn't realize I had in being a product manager almost from day one.

Suzanne: Right. Talk to us more about that moment of panic. I think this is an interesting inspect and adapt moment as it relates to product management in a larger scale organization versus a more startup environment. You made this transition from CSR to product manager in training or product management intern.

Presumably at that scale, they had processes, they had an established way of doing things. The preferred frameworks of thinking were defined and so you got to just soak it all up, and then you went out on your own, to use that same analogy, "Empty field". That was the moment where you thought, "How come I knew it so readily when all of the frameworks are there and then someone took the frameworks away and I got to think from scratch again?"

Justin: Yeah. To give you context at the time at Cars.com, it was a very waterfall environment. To create a product, you had to write an 80 page product requirements document. There were RACI matrixes and you did market analysis and market sizing, you had access to all this data. I think it was interesting. I've used some of those muscles over time and I use some of those skills to put proposals together, but it was an overly rigid process that kind of made you believe you knew what you were doing.

When I finally left to go do product management on my own, I realized that few of those things actually help you in a real world scenario to convince an investor or convince a developer or convince a customer service associate that this is the vision that you have and "This is how you need to do it. Here's how I'm going to break down all those risks in the field."

I think my team here jokes around. We have a Slack channel. We had a new junior person start last year and I asked the team, "Can you put together a list of 'What are the top five things you need to know as a product manager?'" We only came up with one. The title of the list was like, 'Learn the Ropes'. The first thing that came out was, "It's not a rope, it's actually a snake and you're effed." That was the only thing that we were actually able to tell somebody. I think that's it.

Being a product manager is actually, it is an exercise in synthesizing ambiguity and getting people to feel good that you have a vision and there's a story at the center of what you're doing. Telling that story to a developer who wants to build a product, telling a story to an executive who wants to invest in what you're doing. There is no single framework that gets you to understand all that.

I have six product managers on my team and they all have a different style about how they go putting that story together whether it's extremely data-driven or it is told through prototypes and designs or it's told just by getting up and doing a performance piece of art in front of a group of people. Telling that story is key because I think at the end of the day, we're all a little bit scared.

We all want to feel like I did back at Cars.com where you're sure you're going on the right path. Your framework is giving you the right answers to go do things that you're actually going through and you're building the right product. Nobody wants to be held accountable for building the wrong product at the end of the day. Product managers kind of live in that world.

They, on one hand or maybe internally to themselves, always kind of feel that they're not building the right thing or are terrified at what they're doing or if they're making the wrong choice, but outwardly are always presenting the story that like, "We know where we're going. Even when we make mistakes, I can help tell you why we made those mistakes" and make sense of that world. There is that panic and I think maybe the real framework of being a product manager is learning how to outwardly express a clear path that you're heading down.

Suzanne: Talk to us, because you said something interesting there. Nobody wants to be accountable for building the wrong product. Certainly in your career path, you've worked in some large organizations. You're here at Trunk Club. You were at Groupon before, we'll talk about that. These are organizations that started before you and somebody conceived a product. Somebody went from "Here's a pain point" to "Here's a solution" to "Here's how to monetize that" to "Here's how to sustain it and scale it."

There is this changing of the guards moment that happens when an organization finds product market fit, when its earliest product team has to ascend to different roles or sometimes leave the company if it's no longer a good fit for them. A new team is ushered in to shepherd the phase two vision or the crossing the chasm mission, if you will. How does that feel to inherit a product and then have that pressure of "I hope I don't screw it up"?

Justin: It's a great question. I actually think there isn't one of those moments, there's four or five of those moments in the growth of a company. There's getting to your first million dollars and there's a million dollars to maybe 50 or 100 million dollars. There's getting to 300 million dollars and there's getting to a billion dollars ... Each of those stages of growth I think requires a different type of team and maybe a different type of leadership as well.

I really found I like working in the 50 million dollars to maybe a billion dollars range when a company's proven out its initial where I'm not trying to throw a bunch of things against the wall and see what actually sticks and I'm totally terrified that every day I'm not going to have a job because I haven't really validated this product I'm working on. That type of terror keeps me up. I have kids at home and I liked a little bit of stability in my life.

I think there's something really fun about being at that maybe 50 to 150 million dollars all the way up to a billion dollars. There are far different sets of problems that you have to solve and enjoy solving. One of those is growing a team to actually handle product management in your organization. I love team building, I love working with my group, I love the diverse set of skillsets and storytelling that my team has.

There's also product managing the organization. At a certain point, you need to get good about describing to other very specific roles in the organization like operations or sales why it is that your team is building the things that they're doing or convince them that they need those products to actually grow and thrive and survive. I think those are really fun things to go and do.

They're definitely not for everybody. Some people really love being in that zero to 50 million dollar stage where you're spitballing and you're constantly changing, you're pivoting left and right. I like to be in a spot where I can operate out of some data and maybe deal with a little bit of a larger development team and actually go build some really awesome things with some muscle.

Suzanne: How many developers on your team are within the resources of where you are now? Just to give us an example of that scale?

Justin: Yeah. My development team right now is around 70, all roles combined. I believe we have 35 engineers and then we have a mix of business intelligence people and data services, data scientists, designers and UX researchers are also included in that, plus developer operations and those type of roles.

Suzanne: What about the product managers? I think this is also an interesting insight moment for folks listening in is, what does a product manager role look like in terms of radius responsibility? You're in a director level position. What about the folks that are steering the ship? Three, four, ten, how many folks on the team?

Justin: We have six product managers today. We're actually, I think for the size of the organization we are, it's fairly small. We've purposely attempted to try to keep it really condensed just because we've seen, I think all of us here have seen companies where ... I came from Cars.com and there was 80 product managers.

Suzanne: Wow.

Justin: There's a certain network loss. It's really hard to communicate with your own team and product manager to product manager, it's hard to build that trust. One of the things that we've tried to do is keep teams relatively small. There's one product manager for usually a max of seven engineers, a couple of designers, and a couple of data scientists on each team.

Maybe one of the frameworks that we've tried is we try organizing teams around specific types of themes. We have two themes at Trunk Club, but those teams are fully autonomous. They make their own decisions, they form their own roadmaps. My role is not to play the gatekeeper to tell them what they can and they cannot do. I'm more of a sounding board for them. They put their roadmaps together.

Usually we sit down in a small room like this and we try to figure out like, "Okay, let's go through your argument. Tell me your story about why you want to create this stuff. Can you back it up with data? Do you have clear signs from user research or from things that you've actually seen maybe listening to customer service phone calls that this is the right way for us to go? If we can, great. Let's go pitch this to the rest of the company and get people on our side."

We'll do a little grassroots campaign and we'll talk to people one-on-one and sell them on why our idea is so awesome before we ever get in front of an executive team and say like, "Here's what I'm doing and here's why I want investment for it." Those product managers, like I said, are grouped around two different types of themes. We have center box teams. It's a Nordstrom term.

It's basically like a shared resource that we can use across the entire company. We have two of those center box teams today. We have one that's back office which is focused on fraud and finance, product mastering, and then we have a sales tools team that's focused on relationship management and so building tools for our salespeople to manage conversations and relationships.

The other three of our teams are focused around moments in the customer life cycles. We have a team that's focused on the first customer experience, we have a team that's focused on returning customers and getting people back into the fold, call them our activation team, and then we have a team that's focused on bringing the right product to the right person, which is you can think of it's analogous basically to our [inaudible 00:18:35].

**Suzanne:**I guess the thought for me that comes up is as a product manager early on in a career coming into an organization like the one that you're describing, because there's always, I suppose, this question. That's part of what we explore here on this show is, "How much strategy am I really going to get to touch? How much roadmapping am I actually doing versus being given the roadmap or maybe weighing in on a project timeline inside of that roadmap or participating in a prioritization exercise?" Can you talk a little bit about how people find their team? Is it a matter of initial assignment and then saying, "I want to be over here on the ... I'd love to get over to the activation team, Justin, at some point if you could help me."

Justin: Yeah. That's exactly the way it works. We usually start a person off shadowing with another product manager for a time. Very early on here at Trunk Club, we actually had a product manager switch their role every six to nine months. We'd have the same person was managing our operations team when we had it moved over to our merchandising technology team, ended up on our consumer technology team and went around that way until we found where we were best suited.

I think after time, we started finding people gravitate to a specific type of storytelling that really worked for them. The product manager I have in our back office is the most ace project manager I've ever met in my life. She is great about creating a timetable and milestones and deliverables. She works on highly structured type projects like accounting systems or she works on things like product mastering where we're actually creating the products in our system for our catalog.

It requires a very buttoned-up, very risk intolerant type approach. It's very deadline-driven because we have to manage the rest of the organization to these timeframes. She is wonderful at telling that story about what needs to happen and why it needs to happen and why it needs to happen on this particular date and getting people behind her motivated to almost manage crisis every single day. It's very different from the product manager that manages our first experience, which is a very experiment-driven team.

They're trying out different hypotheses like, "I think if we put this in front of customers, they're going to respond in this way." You roll the dice and maybe one out of ten times it actually works out the way you expect. They're managing ten different experiments at a time like, "I'm going to try this out and I'm going to try this out" and then like, "Oh, nine of those things really didn't work".

Very different types of mentalities, I think, for people and where they feel most comfortable telling a particular type of story. I think our goal is really just to create that track of work from the, one things I really found didn't work at Cars.com was that it was a project-based environment. You would write your product requirement stuff and document and actually bid for some developer time.

You actually went up in front of council of people and you put your bid in place, you would try to pork barrel everything into your project. You'd promise it would do the world like, "It's going to clean your dishes and it's going to bring in all the customers and it's going to retain them forever." You tried to bake everything because that project is your livelihood. If you don't get it, you don't have a job. The problem is you get on that project and you find, like I said, that nine times out of ten you're going to fail at it or the premise is going to change.

You, as you're on a project, you got sponsored to do this one particular thing. You can't change the premise of your project. You can't adapt with it and so you're stuck with it. You're stuck defending this thing that may not be the most successful thing for the customer at the end of the day. When we started our system here at Trunk Club, our goal was to create these tracks where product managers didn't necessarily need to justify each individual thing that they were doing.

They just had to maintain a backlog of work and tell a story that was cogent and give people an opportunity. There had to be transparent ... give people an opportunity to actually disagree with that story they were telling or say that story should go down a different path. Our job I think as managers here is really just to find the right track where a person feels comfortable telling that best story based on their own skillset and based on the type of work that they're doing.

Suzanne: You said a lot there and I want to unpack it again. So many good nuggets here.

Justin: Thank you.

Suzanne: You inherited the nugget approach from Northwestern and now you bring nuggets everywhere you go as well. The first is you've painted a beautiful picture of the challenges of a waterfall or waterfall environment or project-based thinking, which is precisely that. Product is continuous, product is necessarily adaptive. When you remove that mindset, you remove a lot of the opportunity to just learn and improve and then you get people forcing situations like you describe.

I want to go back to talk a little bit about stakeholder management and leadership. One of the things that I heard from what you were saying there, which is something that I try to talk a lot about when mentoring job seekers is, who are you? This product manager role looks very different. If there's one theme of the 100 PM podcast, it's that, is it depends.

Getting connected with who you are, what drives you, what environments you work best in, what industries excite you. Are you structured? Are you highly experimental? That's a really critical part of deciding which is the right environment to try to go after. I love hearing that from a management perspective, you're also encouraging that kind of "Let's find your tribe. Let's find your right place in this organization."

Justin: Totally.

Suzanne: I'm reminded in hearing that that a lot of people don't have that luxury. I think it's a great testament to who you are as part of the leadership team. I'm curious what advice you could offer people who don't have as nurturing an environment where they come in, they know they love product. They're also aware that this role they've been hired into isn't the right one and they don't have a supportive leader to say, "Hey, maybe you would do well over here on our fraud team. Let's go and try that." Quit? What do you do?

Justin: My strategy, I've often found myself in that position. My strategy is probably not a sustainable one. I've always worked two jobs. I always work the job that I have and the job that I want. I'm even kind of doing that a little bit right now, too. I moonlight as a developer. I'm trying to build my code practice as best that I can. I think I always said that I would work my day job of being a product manager and putting together proposals and managing products.

After I had dinner or in my case now, I put the kids to bed, I'd go into my office or my quiet space or my safe space and work through all the things I would want to see happen. Sometimes that was dreaming up a new company, thinking about something totally different that I wanted to do and sometimes that was just a proposal for work to do something different to add value.

I think that strategy has served me well in a number of different companies because it's not ... I think the first thing that people want to lean on is breaking down. It's coming into the office and saying, "This isn't working. This is terrible. This inhibits me from doing my job." Kind of like the customer service rep telling his boss, "There's a better way to do things." It gets to be really irritating.

You hear that often enough in your job that you start to block that out a little bit. If you come to your boss with a proposal or maybe your boss's boss or another department and you say like, "Hey, here's a way I think we can do things better and I've laid out the full proposal. I've decreased the amount of ambiguity to knowing this is the right choice and I've told a really clear story about why this is awesome." I've found that that strategy works.

Maybe it doesn't work overnight, maybe it doesn't work within a few weeks, but it works over time to actually find yourself in a good position. If you've truly found yourself in a hostile environment where your voice isn't heard, there are a lot of good companies out there that want product managers, that want storytellers, that want somebody to actually go and help them how to do things correctly.

Suzanne: Right. Yeah, I think you're right. There are a lot of companies that want product managers. I'm deeply connected to the job seeker community and there's a lot of folks saying, "I can't get a job." There's clearly a friction or a tension that's happening there. What do you think that tension is about that the companies that are looking for great people maybe can't find them at the rate they need them, meanwhile the folks that are looking can't seem to get in the door?

Justin: I think part of it is because product management is such an undefined profession, I think a lot of companies don't know what they're looking for in a product manager, don't understand what product management is, and then sometimes when they hire product managers, don't want the output or don't want the outcome of what a product manager's going to give them.

It's a little bit of a learning curve for an organization to really understand that. I've worked for both bosses that understood product management and bosses that have not. It's a pretty night and day difference to know how to manage that, even manage the emotions of product managers, which I think are a fairly unique set across people that I’ve managed in my life.

Suzanne: Are we sensitive?

Justin: I think we are maybe not sensitive, but things like prone to depression. This is something we talk about often in our team. I'll tell a really quick story. We decided to replace Salesforce here, the CRM at our company, and decided to build it ourselves. It was a super scary moment for us.

The product manager that worked on this job is one of the best I've ever met in my life. He's a phenomenal guy. He built this thing and it was an astounding success. We actually built it in three and a half months and we rolled it out to the company. It was one of the quickest projects I think we've ever done. Everybody loved it and there was parades down the street.

Suzanne: I would be celebrating if I could get rid of Salesforce myself, so I'm with you on that.

Justin: We were so happy. My boss had asked me at the time, and he had worked with product managers all his life, he asked me, "So how's he doing?" I said, "You know what? He's actually kind of bummed right now." My boss said to me, and I'll never forget this, he's like, "That makes a lot of sense." I said, "Why?"

He said, "Well, because product managers hold in their heart every single trade-off they've ever made across a product. At the end of that project, you think to yourself, 'Man, I could have done this so many different ways. Did I make the right choices?'" I think that's totally true. I think as product managers, we face that all the time. We live in this ambiguity and we can never show that ambiguity to other people, but internally, we face it.

I think part of my job as managing product managers is to give safe space to them so they can talk about all those difficult things, difficult decisions and celebrate the successes. Sometimes people don't celebrate the success of a product manager because the product manager is mortar between bricks, holds those big bricks together. Holds operations and sales and engineering together, but never really gets noticed.

The other product managers are great about celebrating like, "You had a great demo that was phenomenal. You made a metaphor that you were able to hold onto that whole entire demo. You know how hard that is? I saw your boss starting to fall asleep in the middle of that demo and you did a great job of actually waking him back up and getting him to notice the things that you're actually building." Sometimes it's about commiserating like going to get a drink and saying like, "Yeah, that's really tough and those trade-offs are difficult. Those mistakes, that failure was really tough to hear, but you know, we got your back."

Suzanne: Yeah. No, that's super cool and I'm glad you bring up the point about there's not a lot of glory in the role. I think one of the other nice things about the show is this opportunity to shine a light on all of these amazing people that are doing incredible things. It is a strategic role. There is a lot of aligning different viewpoints.

It's always the founder that gets invited to talk about the success as though they alone created this 50 million, 100 million, 10 billion dollar thing when in fact, there were a lot of people, both the specialists within the domains and then the mortar as you describe that made it happen through trade-offs like you're talking about.

Justin: No, absolutely.

Suzanne: It's beautiful. You were at Groupon before. Groupon has, like, 15,000 people. Something like that.

Justin: Something close to that.

Suzanne: Trunk Club's, what, like 1/10th of that?

Justin: Yeah. I think we're around 1100, 1200 people right now.

Suzanne: Talk to us about that transition to go from the enterprise to ... 1500 is also still a very large organization, but it's not 15,000 large.

Justin: Groupon is actually, you can consider them an enterprise, but they're a fairly unique company. One of the ways I liken that they're managed is actually like a venture capital firm within a company. There are 52 development teams inside Groupon. Each of them is making a bid about what they want to do and senior management is investing those 52 teams across the board ... It's actually, Groupon's environment is incredibly crazy and fast-paced.

I think part of that as well was not only the enormous, the growth cycle. They went from zero to a $6 or $7 billion dollar company in five years. It was almost like the Incredible Hulk. They grew too big for their shirt instantaneously and everything was torn to shreds across the board. That includes their company culture. It was really, really hard to hold onto and they brought in a lot of leadership from Amazon.

I think it was leadership from Amazon that were incredibly aggressive and wanted to maintain particular financial goals to shareholders. The environment if I can describe it in any way was just particularly frantic at all times. I managed teams around the world in Chile, in Berlin, in California. I found myself up basically all hours of the day managing something. My particular team was the storefront team. I actually had two. I had storefront and funnel optimization.

The storefront team is kind of how it sounds. We managed the deal page, the core page on Groupon, all the way through you checking out your particular deal. Every single channel manager, every single operation at Groupon actually had to run through that particular page. Then I managed funnel optimization, which was this cross data science analytics team whose job was to go across every single function at Groupon and improve it in some way and it was insane. It was absolutely insane. I'm not going to lie. I actually, I had a nervous breakdown on the job. Because it was so crazy.

I think one of the things we learned very, very early on was we started looking at ways that we can improve the site and realized that it was taking between six and seven seconds to load a page. In an eCommerce world, that's a total death knell. We could take a look at revenue generation by millisecond on this site and we were just losing gobs of money.

I could do all these things to improve the experience at Groupon, but at the end of the day if the site wasn't actually performant, none of those things mattered. We sponsored this project to actually go through and rebuild the site in Node, because it was far more performant and allowed us to actually do a bunch of things that we wanted and going through this project, realized that over the five years of this massive growth, nobody owned whole sections of the site.

Because I was sponsoring this project, I ended up taking implicit ownership for a bunch of those different things. We ended up owning things like the login form, which doesn't sound like a big deal until you realize the millions of people that are logging in every day and how each percentage of login success matters to a company like that. It became absolutely overwhelming.

I stopped eating and I stopped sleeping to the point where I think my brain just broke down for a period of time. It was super telling. I actually learned a lot in that process. I learned how to manage this enormous scale organization. I learned how to build real-time analytics to understand how things are performing. I actually learned a lot about engineering in itself.

One of the things we were required to do is every day I came in and I turned on these two gigantic TV monitors that sat in front of my desk above my desk. On there was everything from real-time performance of the site all the way through what was going on in the servers, like how many cache hits and misses or CPU utilization. If anything dipped on the site, I had to immediately find the root cause.

Is it some type of hardware performance? Is it something to do with one of the services that we rely on? Is it a deal that's running on the site? Within five minutes, I get a phone call from the CEO saying, "What's going on? Can you explain what's happening?" I built a really good muscle for me to read real-time analytics and to keep monitoring our products, but it definitely took its toll. I think my wife had told me at the time that she thought I'd kind of actually died.

Suzanne: Wow.

Justin: Because she hadn't seen me for months on end. It was really tough. I think I'd gone back to my bosses at the time and asked them, "Hey, could I do a different job?", actually. To use my old tactic, I actually invented a new job for myself and proposed it to them. Their response was, "No. You're actually really good at the job that you do."

Suzanne: Being punished for succeeding.

Justin: They're like, "I've never seen anybody that can negotiate with all the channels of the business and keep things going." I said, "Yeah, that's great, but I'm also dying right now." I think it forced me to really consider the next job that I was going to take. That's when I found Trunk Club. I had a friend who invited me over here.

I came over at about 7:00 in the evening, which is Trunk Club really starts to pick up about that time. Customers come in, they get a drink, they sit down, somebody shows them awesome clothing they can buy. I went from the sales floor down to the engineering floor and was amazed. There was engineers down working on awesome projects and they were all excited. They were happy and they were working on things they wanted.

I got to know the team over time and really decided for me if I'm going to be a product manager anywhere else, if I'm going to deal with the stress day in and day out, I want to work around people who I think are upstanding. Who are going to support me in my darkest hour, who are going to support me through the crazy ideas and the difficult times. People I want to share a drink with and laugh about the thing that we're making and commiserate over the things that have failed. That's what I really found at Trunk Club and really woke me up at Groupon is that that was the prime thing I really needed to find for a product management position.

Suzanne: First of all, thank you so much for your candor and in sharing that. It is a less explored but really real part of it, which is, especially I guess you all don't consider Chicago to be East Coast. I'm from Toronto, so I always just think you're practically Toronto, it's East Coast-

Justin: We're the third coast.

Suzanne: We're in that 9:00 to 5:00, go, go, go. California operates very differently.

Justin: Right.

Suzanne: East Coast, there is a celebrated aspect to go, go, go that is not as readily embraced I think on the West Coast.

Justin: Totally.

Suzanne: That manic environment that you're talking about, I know a lot of it has to do with the scale and with the rapid growth as you described and it's a specific culture, also. Being connected with your own self enough to say, "You know what? There are other things that are important to me than just being great at the job. That's emotional well-being and family relations and balance in my life." I love that you say you've found Trunk Club. Maybe Trunk Club found you. I don't know. There's definitely an arrival moment. Let's talk about Trunk Club for a moment. There might be folks listening who don't know what it is, so give us the pitch here.

Justin: Yeah. Trunk Club is about helping you make sense of style. I think one of the things that we say, for us anyway, we're a Nordstrom company. We sell all Nordstrom clothes. People come in at all different stages of life and we have two different experiences. You can come into our physical location or you could deal with us online only. Either way, we assign you a personal stylist who's going to stay with you throughout your entire lifetime at Trunk Club.

The personal stylist's job is to help you feel good about whatever event you have coming up in your life. If you're me and you're going to talk at a conference a little bit later in the day or if you are going on your first date or you're going for a job interview or you're my wife and you're going to actually pitch your new line in New York and you're seven months pregnant and you want to find the perfect outfit that's going to make you feel great, that's our stylist's job is to fit you in that and to help you tell your own story and help you feel good about the thing that you're going to do.

Like I mentioned, there's two different ways that you can work with Trunk Club, so you can come into one of our retail locations. We're in New York, Boston, Chicago, LA, Dallas, Charleston. You come in, you get a drink, you sit down in a private fitting room with somebody who's going to bring you out clothing. I actually work a lot more in our trunk side of the business. You sign up online, we get to know about you through forms, through actually conversing online through our real-time messaging platform.

Our stylist is going to be there to ask you questions and figure out what you want and then it's actually going to show you a box of clothing. It's going to say like, "Hey, does this actually match what you're looking for for this particular event or where you're at right now?" You're going to say yes or no, "You totally missed the mark" or "This is awesome". We've seen all those responses across the board. You'll get it shipped out to your home and then try the stuff on. Whatever you like, you keep and you send the rest back.

Suzanne: Right. Yeah, I actually in preparation for our hanging out, I wanted to be as versed as I could in the product. I took myself through the entire onboarding process and I was really quite impressed with the intake form. A lot of that is you're asking for sensitive information.

You're trying to capture a picture of somebody and you have to, I would imagine at every moment keep them from bouncing and going, "Ugh, this is too arduous. Ugh, I don't want to share all of this information." I made a mental note and said, "Okay, they did this very well." I do have one piece of feedback. Do you want to take it?

Justin: Yeah, please. Let's go. Let's do it.

Suzanne: When I got to the page, so none of the layouts ... I chose woman as my gender, although I'm not sure that's always the appropriate path for me, but I chose woman and then I went through all the styles. None of them were my style, which is fine. You offer a complete workflow to support that.

When I had to put in my budgets per item, I felt that there should be some not applicables like, for example, a handbag. I'm never going to have a handbag. Then I had to provide a value set which is actually a false set of information. I imagine there may be circumstances like in that. There's an opportunity to say, "Oh, you don't use handbags." That's an interesting framing of who your personality may be.

Justin: Oh, that's fascinating.

Suzanne: It could be useful.

Justin: Yeah.

Suzanne: But given that you have such a manual kind of person-to-person component of the business, maybe they cover all of that over scotch in the beautiful fitting rooms, in which case, it doesn't add any value at all.

Justin: No, that's actually, that's great feedback. I think one of the fascinating things about building those forms, it's something I never would have expected. I think you have to understand this in the greater context of what's happening in the industry right now. Last year, Amazon scooped up somewhere around 60% of retail growth. All these big retail stalwarts like Macy's are worth a third of what they were a few years ago and they're shutting down locations left and right.

I think when you're faced with Amazon who's infinitely convenient and has almost every product in the world, it's like, "What value do you offer?" I've always been very judicious about what we put in front of customers because we want to always keep the experience about the conversation that you have between you and your stylist. What's interesting is that every question we ask, because sometimes even if we don't get the question right, it actually increases the possibility that we're going to convert that customer at the end of the day, which is totally opposite.

Usually in any other business I've worked at, you drop questions or sorry, you add questions and people drop off in the funnel. I think what's interesting is it's the opposite here. I think it has to do with this placebo of personalization. People come in and they expect the more questions they answer even sometimes if they're not perfect, totally understand our stylist's questions are not fully ... they don't fully cover every part of the spectrum that we want them to today. Even just asking the question, people feel like you've listened to them a little bit more. They're more likely to actually go purchase something at the end of the day, which is totally interesting.

Suzanne: For the folks on the Trunk Club side as you described, is this really meant to service everybody else who doesn't happen to be in one of the few urban centers where you do have this physical location? Or it's a complement to, "Hey, if you're here in Chicago, come have that scotch, let's do the fitting, and then let us recede into the background as a convenience service"?

Justin: Yeah, I think one of the things ... so convenience is a really broad word. For some people, it means "I want something within five minutes." For some people, it means "I want you to anticipate what my needs actually are." I think it's both a complement and it's a different experience depending on what you want out of it.

For some people, trying things on at 9:00 p.m. in their house like a single mom, that might her only chance to actually go shopping throughout the day and so that's really convenient for her. For other people, filling out a form and talking online may not be the most convenient thing in the world.

Coming in-house to our location actually may be super convenient because you could talk to somebody face-to-face and have them actually assess your body right there and understand what's going to fit you and what's not, what's your style and what's not. We try to offer multiple modes in which people can work with us. We see sometimes that the same customer may want to actually go get a trunk that comes in-house every so often and maybe looking for very different things at different times in their life.

Suzanne: I love the concept. I love, as I say, to go back. The user interface is super clean.

Justin: Thank you.

Suzanne: I'll be tracking because it's an interesting space to be playing in. We're definitely the outsource economy. I had my own kind of probably Trunk Club pinch point when the seasons change. I go to pull out all of my t-shirts and then I realize that the t-shirts that have served me well the past few summers don't work.

I'm a great example. When I say convenience, I think, "Okay, I just want someone to go to James Perse and get me three shirts all in the same size and cut, just three different colors. Where is that person?" It sounds like that person might be a part of Trunk Club. They won't go to James Perse, but you carry James Perse at Nordstrom's locations.

Justin: Actually, my convenience is, and don't tell anybody this ...

Suzanne: You're telling everybody. Yeah, keep going.

Justin: I hate dressing myself in the morning. If I could wear the same uniform every single day, I probably would. We have our custom clothing division here and it's great. I actually just had the same shirt manufactured, like, 15 times and I just can wear that every single morning.

Suzanne: You're taking a page from the Zuckerberg playbook. Just like, "Same outfit, then I can have all this extra bandwidth to think about making the product better."

Justin: Yeah. Give me my custom gray hoodie.

Suzanne: Let's talk about, we do a segment here called 'Get the job, learn the job, love the job.' I'm a first-time PM or a novice PM. I'm looking to get hired. I heard you and I think, "I want to work with this Justin guy. He sounds loving and caring and the kind of leader I want to be a part of his team." How do I get hired? What can you tell me?

Justin: Yeah. We've hired people from all walks of life. I think we talked about me maybe having a little more traditional thing called that product management background or maybe more formal. I think everybody that's on my team comes from some disparate place: analysts, consultants, customer service, designers.

I think first and foremost, and this is super easy to forget, but you have to be really passionate about the job that you want. I can't believe how many people that we have apply and just show no interest in the position itself. They come in the door and they're like, "Yeah, this seems kind of cool." Or, "Why don't you sell me on it?"

Suzanne: "Maybe I want the job. I don't know."

Justin: It's such a night and day difference when you walk into the job. I had one of my product managers come in and bring together a proposal of like, "Here's how I would improve Trunk Club" just like you did on this call, so maybe if you want to come work here at Trunk Club.

Suzanne: What do you think I was doing? I was seeding that for our offline conversation. Go on.

Justin: "So I went through the service and I actually think there's a couple ways it could be improved. I built this customer journey map." I was so floored that this person did it and they had the whole presentation put together, actually did user interviews with some of her friends that used the service. That's super impressive at the end of the day. I think part of that also demonstrated the other thing that I'm looking for and I've said a couple times, which is, I want somebody who's going to be a good storyteller.

Tell that story however you want. If you want to tell that being super data-driven or super prototype-driven, that was the really big selling point for me is like, "Hey, can you actually go through and tell a story about your own career and things that you've done and things that have actually led you to this point?" It's a huge selling point for me actually coming on as a product manager here.

Suzanne: What about the hard stuff? You shared from your own career those challenging moments, those vulnerable moments. What can you say about the hard part of being a PM?

Justin: Yeah. Hard part of being a PM. I think there's a couple of things. One table stakes is, are you perseverant? Can you get up and come into the office every day and do this job? Can you be a different person every day to a different person that actually needs you to be that? Can you be a leader of engineers? Can you go on a sales call and help somebody out? Can you answer a customer service phone call?

It takes a lot of perseverance to be able to do that. I think hand in hand with that is humility. You're going to have to learn tons of new things every day. I find the people who are the least successful in the position are the people who say, "That's not me" or say things like, "That's too technical" or "I don't think I can understand that".

I think a person who does a great job as a product manager, this person comes in with an attitude of like, "Yes, I can learn that. Yeah, I could fake it until I actually, I'm able to make this thing. I can get into the mix. You want me to understand a program language? Great. I will sit down with you and actually work through it until I fully understand it. You want me to understand how to put a financial plan together? Great. We'll work through it til I understand it."

I think it's really hard for some people to admit, especially as an adult, that they don't understand something and they need the help. They may be the stupidest person in the room or they may be sitting with the smartest person in the world in the room to learn something. It's really hard because that's a really vulnerable moment to have.

Suzanne: Yeah. No, this definitely comes up a lot is resist the temptation to be the specialist. There's always going to be folks that are smarter than you, so you have to be comfortable with that and equally, you got to find a way to connect with these people. You can't connect by taking the standpoint of, "I'm not going to learn your language."

Justin: Totally. Matter of fact, we joke around that we're the chief janitors here at the company.

Suzanne: You're the mortar, you're the janitor. You're making this role sound ... anyone listening is going, "Forget about advice on getting the job. I don't want this job. Too much clean up."

Justin: I think it's fun, though. Every morning I come into the office and I put away the dishes. It's the first thing I do every day that I come in. I think that's what it takes to build a successful product. You have to be the person willing to write the stories, to actually do the testing if it needs to be done, to find the bugs, to listen to the feedback about your product even when sometimes it's hard to hear. It's difficult to be that person, but that's what it really takes to be an awesome product manager.

Suzanne: What is your favorite thing about being a product manager?

Justin: I think despite all those things, being the janitor and the mortar, it's almost like an addiction. I think being a product manager, you have full control of your own destiny. You have full control of your own destiny. You come in every day, you get to decide what you're going to do, you take full responsibility for the mistakes and you get to celebrate sometimes even if it's internally about this awesome success you were able to do.

Even though working at Groupon was one of the toughest things I ever did, I made $56 million dollars in a year for that company. I will remember that in my heart and I'll remember all those successes I had and all those things I learned and all the friends I've made along the way for the rest of my life. That's a really hard thing to turn down.

I talk to my product managers every week about this and we check in often like, "Is this still the right job for you? Are you still in it? Do you want to move over to a more specialized position?" I think universally I find the people who I work with say the same thing like, "I can't give this up. I may have had a sleepless night last night, I may have had a really tough meeting with our boss, but I can't give it up for the life of me."

Suzanne: Do you have, Justin, any recommended resources that you would like us to add to our site? Books, blogs, podcasts? Just great information that you think folks could benefit from coming across?

Justin: I have kind of a tough time with that. I find I actually when I read, I try to read things totally out of the industry. On the train in in the morning, I try to read science journals because sometimes I need a break from what's going on in the world and in product management. I find often what I'm seeking in my job is a good metaphor, a good analogy, something else I can try.

Sometimes just reading stuff that's incredibly disparate from what I'm doing right now but is also about making sometimes ... my wife is a wood maker. She's a professional wood tuner and I just like to be in the shop with her. She makes things, which often gets me to think about building products in a totally new and unexpected way that I would have never thought of before.

Suzanne: That English degree. Who knew all these years later it would just be paying for itself in dividends? All right. Normally I like to wrap up by asking folks about a personal or professional mantra, but as you've been talking, I've been thinking I have one for you.

Justin: Okay. Bring it on.

Suzanne: Bear with me. I know I'm just projecting a lot onto you, but I want to propose "Know thyself" also because it really maps back to classic literature piece. I think what you've exemplified in this conversation and in your career is the importance of, "Who am I? What drives me? Who do I want to be in the world and how do I reflect that?" I think it's certainly what I think that you have demonstrated.

Justin: I love it.

Suzanne: See how it sticks. I don't know.

Justin: I love it.

Suzanne: Okay. Justin Hughes, thank you so much for being a part of the project. So great to meet you.

Justin: It was great to meet you, too. Thank you for having me here.

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Trunk Club

Trunk Club was started to solve a simple problem: shopping for clothes in stores is overwhelming and inconvenient. With Trunk Club, you’ll discover great clothes that are perfect for you without ever having to go shopping. We combine top brands, expert service, and unparalleled convenience to deliver a highly personalized experience that helps you look your best.
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Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.