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Digital Design Leadership: Jeff Kushmerek


Jeff Kushmerek cracks a few jokes and talks to us about the unique evolution of his career from developer to CPO of the Boston based company Flashnotes. Having the insights of both design and leadership, Jeff knows what truly encompasses a digital design leader.

Hear from the other digital design leaders we interviewed


Jeff Kushmerek: So, I’m Jeff Kushmerek, I’m the chief product officer for, we are an online marketplace to help students sell their course materials to each other and basically, they’re helping themselves by selling material and they’re helping students by doing better in their classes. I oversee all of the product development. Not only am I the chief product officer, I have design and test underneath me because that way I’m sort of the final gatekeeper to say yes, that looks great. And I’m the scrum master. So at a startup you do lots of little things and I love doing that, that way I never have to say what’s going on with x, y, and z.

Richard Banfield: So the path of leadership for you has been quite a colorful one.

Jeff Kushmerek: You mean the hair I have to color, because I’m gray, or–

Richard Banfield: Tell us a little bit about how you’ve kind of stepped through that.

Jeff Kushmerek: Sure, I actually started off as a developer back in the nineties. I was doing a lot of database work for law firms. They were moving from paper into electronics. You know you had– you represent Ford and Ford’s always getting sued for X, or this paper is getting always– so, I’ve always been in this sort of information access problem. Because I was doing the development, I was then doing pre and post sales development for another company, and then we were working on an API for financial companies, but in that day everything was HTML and divtext. Then, all of a sudden this crazy little thing called XML came around, and the said, ‘you know, we love your stuff, but you got to be XML, you got to be this, you got to be that, you’ve got to be .net. These are our biggest customers.’ So I kept filtering these features back into he product team, and they’re like, ‘you know something, you’re the only guy who’s working on this stuff. We would love it if you could be the product manager for that.’ So I stepped into that role, and I did that, and then I switched over to another company called Endeca, and fast-forward to two or three years ago, they were sold to Oracle. But they were really solving this information access problem. There’s so much data that’s starting to accumulate on the web, how do we get users to what they want in three clicks? So they created this search and browse technology, I was working in product there. And then they– we stopped working– well, we were always working on some of these sort of low level customers with small problems, but then our success started getting us into really big problems. And because I knew what we were doing technically and via the product, with some of our analytical products as well, that they asked me to go into the professional services team, and sort of that higher level client management but pre-salesy type of role as well, too. So we started working with all of the big, top 100 retailers, also had an analytical product. So we did that for a while, it was great, it was awesome, and then another company Brightcove came along. They were like right next door to us in Cambridge, and they had just started a small, small little creative shop out of a team and they were like, ‘let’s see how it works!’ And then they were like, ‘wow, this is actually working really well! We don’t know what we’re doing with professional services. Let’s go find somebody who knows professional services.’ Because there a period, and I hate to sound like Rosemary, but there was a period at Endeca where we were just going through this massive growth spurt. Like we were a team of 25, and now we need to be a team of 100 globally, and so I was actually taken out of the line, the service line to work on this team that was basically, best processes to get up to the speed. So that’s when you start learning about budgets and profitability and partners and all this other stuff. So I took knowledge to Brightcove and we just started– we grew that team from 4 to 25, a nice big PNL. We went public, and then the life of a services person is a lot of travel. I had my third daughter was born. And suddenly I didn’t feel like being in China one week and Germany the next week for a global company. So I just was like, maybe I want to get back into product. I still felt like we were always doing product work with our customers, right? What’s you’re requirements? We can go build that for you. We’re an adjunct part of your product team for a little while. We were working with all of their product owners and sometimes even their graphic designers and their QA people. We just kind of bolted in there. So, it seemed like a natural thing. I went to go work– but I was still on the edge. So this fledgling music called me up and said, ‘we’re having problems with our product, I think we really focused in the wrong area. We want to give it another shot. There’s not too many people with consumer-facing experience in the Boston area who just build enterprise apps in this area. So I said, sure! I love music, and if I can’t get my act together on music and product it’s back into the services world, and I’ll see my daughters when they’re fifteen, so I wound up loving what I was doing, getting back, talking to users, doing all that fun stuff. Getting up to speed with this great MVP, Minimal Viable Product philosophy; that’s how we roll in services, what do you need built right now? You want 15 things, you gave me a budget for 10, let’s work it out here! You have this and you have that. So I took that philosophy and we rolled with it. The music thing didn’t work out that great, but Flashnotes called up and they said, we’ve got this idea, and we want to bring video into it and we’ve heard that you’re the guy, because Brightcove is mainly video, and it actually worked me because it’s really the blend of stuff I was working on: commerce, video, and just getting back into it. So I went along– that’s the colorful history of it.

Richard Banfield: So obviously, when you’re growing up you don’t think of yourself as a product lead or a product owner. At what point did you have that realization that you were in a leadership role?

Jeff Kushmerek: When you asked me to speak? I would say…

Richard Banfield: Well, have you always been a leader, and this just happened to be another culmination of that?

Jeff Kushmerek: Yeah, I’ve always– well, it’s weird, you feel weird saying, ‘I’ve always been a leader.’ But I’ve always been asked to fill in in whatever the most important thing is. Like, there’s a problem, we need you to step in and fix it. So, first there’s problem solver, and then I think it was really when I stepped into that role at Endeca where it was like, we’re trying to grow this. We want all the best practices. We want all of that. I was sort of like the lead senior project manager for a while and helping mentoring people, so I recognized that. ‘Oh, maybe I’ll actually have something to give here.’Then I noticed that, so my problem was always that, I always just thought that this was what everybody else was thinking, like, oh that’s easy, you just go in, you talk to the customer, they tell you this and that… And so when I started managing more project managers at Brightcove, mentoring more. That’s when I was like, okay, I’m not just b.s.-ing, there’s actually stuff that is transferable knowledge here. I actually really enjoyed that. And not just before PMs in that it was I started having to hire more managers underneath me. You always have that hire the best developer and suddenly they’re dev managing now, so you’re working with them on their dev skills and stuff. So, and then it was sort of a slow progression, where I’m suddenly going to exec-staff a lot more at a public company, and then I joined that music company, it’s, we’re looking to you to make these decisions’. And then suddenly, it’s like, ‘we need you, the old guy, to help out–‘

Richard Banfield: Seasoned I heard. Seasoned is the word.

Jeff Kushmerek: Seasoned! Yes. Seasoned leader to help come in with that pattern recognition to help say, ‘yeah, that’s great. What I’ve seen is x, y, an z.’ And that’s the role I really enjoy doing right now.

Richard Banfield: So, between being just a developer and now where you are as this chief product officer. The person, the personality, the characteristics, do remember any big moments where you thought to yourself, ‘Shit! There’s something I’ve really got to work on,’ or, ‘there’s something I’ve really got to change in my personality.’

Jeff Kushmerek: There’s lots of them.

Richard Banfield: Too many to tell? We can edit!

Jeff Kushmerek: No. My big problem, and I remember having a one on one–not big problem, but– the thing I always work on is being too high at one point and being too low the next. And when I was a developer I wasn’t–

Richard Banfield: Do you mean in terms of energy or–

Jeff Kushmerek: In terms of like– yeah, everybody knew when I broke something in code because my first just rattled the desk and everything on it– my five coffee cups rattled.

Richard Banfield: So this is an emotional rollercoaster.

Jeff Kushmerek: Yeah, so it was always work on that emotional rollercoaster. I mean, it’s great for sports because you flip that switch and you go crazy. You’re like, ‘hey, how’s it going! Oh okay, the ball’s back here, let’s go kill somebody again!’ So it’s like reigning that all in and keeping your emotions in check and then realizing that it is a rollercoaster. Everything’s a rollercoaster. And people don’t respect you if you’re flying off the handle and saying, ‘that’s bullshit!’ and this and that. And suddenly when you’re leading people on projects or even if you’re just the project manager and something really bad happens, just to be like; you know, these things have a way of working themselves out. You see, when you freak out, other people have that look in their face and that’s like terrible! It’s like, ‘I don’t want to see daddy yell!’ And so you realize suddenly at some point that you’ve got to control your emotional outbursts or it has a direct impact on other people.

Richard Banfield: Being a good leader is managing those things.

Jeff Kushmerek: Exactly, exactly. So, always working on that. Now, I will say that you should not stop your passion. There was always that, ‘you got all in somebody’s face and exec-staff!’, and I’m like, ‘yeah, because he was wrong!’, and we really had to go down that path, and yes I will step back and you can’t take things personally. I know and we talk about great stuff, and we’ve gone over great stuff in these meetings and the previous event as well, too, and we all smile and we be nice and friendly to each other, we should be that and everything. But I think there’s a point too where it’s okay to be passionate, and to occasionally show that you can get angry about something, but it’s because you care. It’s not like, ‘I hate you’, it’s like, ‘I really don’t think that’s a good idea!’ I’m going to calm down and talk about it, but this is why I’m not trying to be a jerk, I’m just passionate about the issue. So yeah, that’s the thing I still work on. Hopefully I’ve done better.

Richard Banfield: So, then describing yourself in terms of the style of leadership, how would you do that to somebody?

Jeff Kushmerek: Yeah, so I’m not going to ever be Jack Wallace or Joe Wallace in GE and Fortune 500 company, like I know right now I love what I’m doing which is being myself, working with small teams, I’m going to be dropping 30 Rock and Big Lebowski quotes and I’m sorry, that won’t get me into the board room at some of these larger companies. I’m not going to be Fidelity’s exec– I have friends that are doing awesome at big companies, and they button it up, and they wear the suits every day. That’s awesome, I’m very happy for them. I would rather have a couple of drinks and let it fly. Saw a little bit of that today, but never let it go crazy, out of hand, and stuff like that. So it’s a little, you know, I am myself. And I’m very happy where I am, and I never say, ‘oh, I should have really toned it down’, or reigned it back in there and stuff like that.

Richard Banfield: So when you’re hiring, are you looking for similar qualities?

Jeff Kushmerek: Yeah. Am I looking for similar qualities? Yeah, you know, I like to see– everybody fills a different role, so I’m not going to say if they don’t laugh at my jokes, they’re out the door. But you do– it’s a startup, and like we mentioned upstairs that we’re with each other more than we’re with our families sometimes, unfortunately. So, you do have to kind of have to work with people that you’re going to enjoy working with. But not everybody’s got to be knee-slapping, somebody’s got that slight sardonic smile almost when you say something funny. It’s the– are they not on that other opposite end of that? Like, that person’s a jerk, but man they can design their way out of a paper bag. It’s not going to work out for you, you know? And hopefully they’re going to say, ‘that got a little bit too much’, and I appreciate that. I remember I was talking to somebody doing my thing during an interview, and I was like, yeah, so you know we’re going to compile our interview feedback and sit with each other, and we’ll really want to be back in our responses back. And this guy was like, not in any rush, and I was like, ‘okay. He’s not going to be here,’ and that’s great. And just like I said, ‘You should never be in that massive rush to hire the wrong person. That person who’s dying for a job because he’s got mouths to feed, you should never jump into the wrong thing, because he’s going to be unhappy with me, or my style, or unhappy with the job that’s put in front of him as well.

Richard Banfield: So looking for complimentary skills as well.

Jeff Kushmerek: Yeah, yeah. We should always fill in those holes. You don’t want people who are just going to be a replica of yourself, too, as well.

Richard Banfield: And have a bloody good sense of humor at the same time.

Jeff Kushmerek: You know, everybody should bring something to the table.

Richard Banfield:  It’s what gets you through.

Jeff Kushmerek: Yeah, it’s just a great thing. You know, you look around and everybody’s having a great time, and the introverts can at least be internally laughing and enjoying the fact that they like the environment but they don’t have to be sittin there doing what they think they have to do to fit in. They can be enjoying the fact that they’re in a loose environment. If I was very succinct, I would have said, I keep it loose.

Richard Banfield:  I got my answer!

Jeff Kushmerek: I keep it loose, Richard, that’s what I do!

Richard Banfield: So, anything that you’d do over; anything that you’d like to do again?

Jeff Kushmerek: I got interviewed yesterday and somebody asked me this, and came across with a little bit of an inappropriate metaphor, but we can edit it out, as they say.

Richard Banfield: There’s nothing inappropriate here, trust me.

Jeff Kushmerek: There’s nothing inappropriate here. So, my answer is that I would do nothing different. Okay, that’s the ‘cool thing’, like that Kushmerek’s a cool cat, right?

Richard Banfield: Right, he’s got no regrets.

Jeff Kushmerek: No regrets! And my metaphor is this, I went to a high school reunion.

Richard Banfield: This is not a metaphor, this is a real story.

Jeff Kushmerek: You’re right. I always mess up that metaphor, simile

Richard Banfield: This is a memory. This is just a complicated memory.

Jeff Kushmerek: I took a very convoluted, complicated memory and made it

Richard Banfield:  I’ll make it a metaphor.

Jeff Kushmerek: Okay, maybe we’ll tear into this with a college memory. And so, somebody says something on a Facebook comment, you’re not going to connect it to them like, ‘that’s the girl I really messed up with!’, right? ‘I should have really– I wish I didn’t drink as much, I wish I didn’t say x, y, and z, or do x, y, and z that broke that up.’ I don’t think that way. I think I love my wife. I love my three children. And if I done that right thing with that person–

Richard Banfield: You wouldn’t be where you are today.

Jeff Kushmerek: Exactly! And so I’ll take it to the creative director discussion that I had with you probably like six months ago. I was looking for this be all, end all character. ‘I need you to do my perfect UX. I need you to do my perfect UI. Do the marketing stuff and–‘ It’s not there, right? I hired somebody that didn’t work out. Now, I can say, ‘agh! I hired the wrong person. I’m such a jerk! I should have thought about this!’ Now, I’m in the position where your team went off and created exactly what I looked for gave me that additional buttressing of expert knowledge, and brought my thoughts up to where they need to be for 2014, and then I can then bring somebody young, and passionate, and just hire this guy who’s so excited to be working for us, and I’m not saying, ‘guess what! Let’s turn this whole site around for us!’ And he’s like, ‘oh my God!’ And so– I’m exactly– I’m very happy with how everything’s worked

Richard Banfield: No regrets. I like it.

Jeff Kushmerek: No regrets.

Richard Banfield: Cool, Jeff, good talking to you.

Jeff Kushmerek: Any time, man.

Richard Banfield:  Any time. Thanks man.

Jeff Kushmerek: You got it!

Author Richard Banfield

As CEO, Richard leads Fresh Tilled Soil’s strategic vision. He’s a mentor at TechStars and BluePrintHealth, an advisor and lecturer at the Boston Startup School, and serves on the executive committees of TEDxBoston, the AdClub’s Edge Conference, and Boston Regional Entrepreneurship Week.

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