Career interview with Mike Tschudy, Head of Design at

I had the pleasure of talking with Mike Tschudy about his career path recently. Mike is the Head of Design for He shared a ton of good advice about intentionally planning your career, finding good sounding boards, and taking a step back occasionally to reevaluate your path. The full transcript of our discuss is below the video.

Transcript of Career Interview

Larry: So today I’m with Mike Tschudy. He’s the head of design at, which was acquired by Intuit a number of years ago (if you all remember). Mike and I have known each other — gosh man — probably for about 20 years — at least.

Mike: Yeah, maybe 25.

Larry: Yeah, because we both worked at Apple many many years ago and then we got to know each other at eBay. It’s where we spent a lot of time kinda working together day by day. So today I’m just gonna talk with Mike a little bit about what he does, and his career path, and just get some advice from somebody who’s been doing it for awhile and been doing a great job. So why don’t we start out with that, Mike. Why don’t you tell us a little bit about who you are and what you’re doing right now.

Mike: Yeah, my name is Mike Tschudy. As Larry said, I’m the head of design for I’ve been in Silicon Valley for almost 25 years and have really enjoyed my career path. It’s never been a straight line, but that’s what makes it interesting. Actually, how I ended up at wasn’t a straight line.

Larry: Right. So do you want to take us back a little bit. I mean I think it’d be interesting for people especially who are interested in the path that you took. Go back to where you started with your education and the jobs and companies that you’ve been at, because you’ve been at a wide variety of places.

Mike: Sure. I have. So, let me just start with high school. I went to a great school, but I was not a great student. I was curious about a lot of things and lacked a lot of discipline to do the hard stuff. The easy stuff, I was really great at — when the things came easily. And I was committed in deed, but maybe not in thought, to go to the Naval Academy. And when I didn’t get in, I didn’t really have an option B. At that point I was living on the East coast, my parents — my father retired from the Navy, and moved to Ohio. And, so, well, there you go — I guess I’ll go to Ohio State. I went to Ohio State because I was a decent athlete, and so I walked on and played varsity Lacrosse at Ohio State, and there I was trying to figure out what to do. And when I reflected on my time in high school, I realized I really enjoyed English literature, I was very good at it, and I had suppressed a lot of my art and design experience in that process. So, I said, “Well, I’m just gonna go and be an English major.” In the pursuit of being an English major I tried a lot of things. I tried Engineering. I tried Education. There were things that I was good at, but didn’t really enjoy, and so I took a wander. It was really in my junior year in college that I had a girlfriend, at the time, who was an industrial designer, and I had this epiphany of going, “Wow, that is exactly what I want to do!”

Larry: That’s cool.

Mike: And I had the luxury, we all had the luxury at that time, that college was a lot less expensive than it is now. And so I was allowed to make mistakes. I just destroyed my grade point average in the process. So I wasn’t very smart about how I experimented — there were others who were much smarter — knowing when to get a “W” (withdraw) — so I switched majors — really had a dual degree in English Literature and Industrial Design. Industrial Design was like Architecture, it was a sequence of classes that have to progress in order, so I was signing up for another three years, and I thought at the time that I really wanted to do Automotive Design. So I went and worked in Detroit for a year, very near my graduation, with General Electric Automotive, and they were working with all the big automotive manufacturers and design houses. I left a little dissatisfied — came back and finished up some classes, and discovered Human Computer Interface, and walked on — sort of — I tend to walk though side-doors —maybe.

Larry: That’s a good tactic!

Mike: Walked on to the Cognitive Engineering program which was Human Computer Interface. And literally did a two-year audit of all the work, and my mentor, Dave Woods, just allowed this ad-hoc, crazy student to be a part of his world. At that point I was curious about what was going on on the West coast, so I did a tour of the West coast and went to Apple, went to Frog, went to IDEO, and just talked to everyone. And that opened the door for a lot of folks from Ohio State, in that program, to get out to Silicon Valley, and one year later I had an internship at Apple — my dream job. And I was, and then I ultimately got hired in the advanced technology group. And I felt like, wow, I had arrived. The problem was that I brought many of my bad behaviors from college with me. I had a wake-up call while I was there and had to re-focus on what was important to me. And then as we all experienced, Apple did a massive lay-off when Steve Jobs came back and he re-focused and pared the company down and that was just a great opportunity for me to get out and reflect. So, at that point I took stock and asked myself what I wanted to do and ended up doing a year at Daimler-Benz Research — planes, trains and automobiles — where I brought a lot of my experience doing automotive design and my experience doing mobile products from Apple — the notorious Newton. But then, after that, I got bitten by the start-up bug and went to Healtheon and that turned into WebMD and went through an IPO there. I became the design manager there, and sorta got bitten by the bug and was just at that point in my life where my wife and I had twin boys and I kept getting bitten by the start-up bug which is typically the wrong time to get that — when you have twin boys in Silicon Valley.

Larry: Yeah, that’s true.

Mike: And then went to an agency start-up, where I was one of the senior leaders and we weathered the Dot Com bubble because our big customers were Fed-Ex and Morgan Stanley.

Larry: Oh, Smart.

Mike: And then when 9/11 happened, all the bricks and mortar, you know, collapsed, and so at that point I was then into another start-up — an enterprise start-up with some folks I’d worked with with Healtheon. But it was a tough time because the market was shrinking and reacting negatively to, at that time, which was hosted solutions, what we call today “cloud.” And so they just couldn’t get a toe hold in that space. And that’s when I came to eBay, and worked with you there as a design leader. So, you can, you mentioned my long and winding career, and this is a good example of that, why I have arguably what’s called the “Silicon Valley Resume.” Lots of two-year, one-year, type engagements but those were where I honed my ability to make good decisions about the climate of a company, and separate the company from my day-to-day and make some decisions to pivot in my own career. And you could call it job-hopping, but gosh, everything was company hopping at the time…going up and down at fairly radical rate. And then there I decided to go to SAP because of the stability, and I realized I needed to buy a house and I needed to start growing up a little, and so for seven years there I went from working very closely with Hasso Plattner, Chairman of the Board at SAP and Founder, to bring that start-up world into SAP. I actually had a great experience there — just loved that company, and the people working there, and I have life-long friends from it. And then took on a role as the global head of Cloud Design at SAP, and that’s where I had a critical moment. You know, my boys at that stage were 14 years old! And, no lie, that’s the time that you need to spend more time with your kids.

Larry: Yeah, that’s a good point.

Mike: And I was traveling three months out of the year. So, I wasn’t expecting it, but I got a call from a friend at Intuit, who said “H ey, would you be interested?” and I really wasn’t until she mentioned Mint. And I loved Mint. I was a Quicken user before that and I loved the mindset and the attitude that created it, and so I jumped to Intuit in a much more junior role than what I was used to playing because I really dug deep on what I wanted to do and that was to build product, design product and ship product at a higher rate and to really take what I would say is a product or business model that went halfway and take it the whole way. I also have this sort of un-ending faith that you can innovate in large companies, but it’s clearly not easy. The other thing that made it easy is the company was literally across the highway from me. So it was really no effort.

Larry: Nice commute!

Mike: Yeah. So, I walked to work today. Which is…

Larry: Yeah, that’s nice.

Mike: I’ve been doing that for over a year now. So there was a lifestyle component, but it was really about leaning into an extraordinary product and slowly just sort of falling in love with Intuit, and what they’re trying to do from a bigger mission standpoint. And that’s where you find me today.

Larry: Right. So I like…I think you’ve said a few things here that I think are important in terms of advice for other people is that it seems like at many points you intentionally took kind of a breather and took a step back and said, “What do I want next for my career and for my life?” Because some of the decisions you made were to improve your life, not just your career. And then treating those jobs as strategic stepping stones to get yourself onto a path that you thought would lead you to a better place, and it obviously has. So I think that’s a good piece of advice. Is there any other advice you would give folks? Because you’ve obviously made some good decisions, there’s probably a few you’ve kinda had to back up a little bit and go forward again, but any other advice you’d give someone who’s looking at your path and is interested in essentially doing what you do?

Mike: I think reflection and taking stock is important. It’s talking to people who are like-minded, who can share feedback with you — about you. Saying, “Hey, have you ever thought of this?” Sometimes we can get so locked in to our world that we don’t reflect on ourselves.

Larry: That’s true.

Mike: You know, in my case, my wife is just an amazing partner, so she was always someone that I could talk to openly about things. It’s easy to bottle these things up and to try to do all the emotional heavy lifting yourself, and I think that’s a mistake. You need to have a trusted network. Someone like you, Matt Holloway, Ishantha, were all really core. And we talked all the time about critical career issues. It got personal. We dug into a lot of the details. Things that were often taboo to talk about when you’re trying to project yourself as a leader within an organization. It was an opportunity to be vulnerable with folks. Often it’s easy to find someone who you connect with because you are in a more elevated position, but this was a group of peers who were probably the best and brightest that you could work with and so I was deeply privileged to have those relationships.

Larry: Yeah, that’s a really good point. It’s one of those things, and I know you’ve discovered it, as you move up in your career and you move up to executive level type of positions is, who are your mentors? Who is your sounding board? Who can you trust? And that’s hard, because it’s hard to have that conversation with a boss (I’ve got lots of stories of why that can go wrong), and you can’t really be vulnerable and have those conversations with your employees because they don’t want to see their boss questioning things. They get nervous because you’re supposed to be a rock of stability. I mean, it is this relationship that we’ve had for 20 years and that we’ve all gone into different companies and different types of roles, but being able to bounce ideas honestly off each other and being able to get feedback and not worry about being vulnerable. I think that’s a really good point. Because it’s hard to find that.

Mike: Absolutely! And it’s a sounding board. It’s a wake up. It’s like, well, if he’s thinking about that, maybe I should think about that as well.

Larry: Exactly.

Mike: I’m having to unwire myself from being insecure and arrogant at the same time about who I am. Insecurity means that you’re afraid of letting your guard down. Arrogance means that you don’t look beyond your current ability, and you put things in their boxes, and shore up and justify your current course. You know, I’m thoughtful, I’m rational. Well, it turns out we’re not. We’re highly emotional, not matter what we say. And I think being able to let that guard down, to be able to be self-critical, to put on a learning mindset — so Carol Dweck’s Mindset book is a fave — and I try to re-wire myself every day. To be open, to ask questions, to be ok with not knowing, and being dumb in a meeting. And more often than not, it’s paid off, and it helps me sort of change my course, in almost every aspect. It’s not just about business. It’s about my health. It’s about my relationship. It’s about my interests. It’s about those disappointments of unrealized dreams, that can change, and re-focus, and re-energize.

Larry: Yeah, absolutely. So I’m gonna switch gears a little bit and this is more coming from the perspective of someone who’s in the industry and they’re trying break in, they’re trying to get noticed by someone like you, trying to get hired by someone like you. I get asked this question a lot. I spend a lot of time on Quora, because there’s so many people looking for answers. Everybody is sending their resume in, their CV, and they’re applying through HR and staffing, and they’re like “Nobody notices me! I don’t ever get a call!” And so I have some advice that I give, and I’d love to hear the advice that you give, because you’ve built teams for many, many years. I think you have a good eye for talent. So what would you tell this person. How can they get noticed, and get a chance with someone like you?

Mike: Sure. Well, so if I speak about design in Silicon Valley, people like me want to hear from you. So know that you don’t have to be precious about time, or what have you — be bold. Reach out. Make sure you’re putting all the digital breadcrumbs out there about who you are. Make sure you have an on-line presence. Make sure you begin to build references and referrals from other people. Because they’ll say, “Oh, I can’t do this, but I know someone who can.” And those are little door openers. Respond to the recruiters on Linkedin, and bring them in. It’s just a mill, you don’t have to pay attention, you don’t have to do what they are asking you to do. That’s how we find folks. I’ve hired a lot of folks recently straight out of school or just out of school, and my recruiters are desperate to find them. A big part of it is that you need to put a digital tattoo out there around your design work. The other thing is, it’s not, a portfolio is just not good enough. I want to see your thinking. I want to see your process. I want to see your sketches into the overview, process flows, into what is the customer thinking. How are you going to delight them? At the end of the day, design is a discipline that lives within an engineering environment, more often than not — or a business environment, and it’s not a stand alone entity. It’s dependent on collaboration. So what is your working model? How do you work together? Are you a “die on the hill” designer (meaning that you will fly your design all the way into the ground), or are you adept at making trade-offs? Can you speak about the business, or the technical, as well as the human and design aspects of it? It sounds cliche, but you think about the T-shaped person. You know, that’s where you and Ishantha and I used to talk about the differentiation that we may have had. It was based on our willingness and openness to think about problems from all angles. At the end of the day, I’m not interested in hiring a designer, I’m interested in hiring a Mint Designer. So I want someone who has passion for the topic, who is an absolute user of the product, who knows the product (what’s good and what’s bad), having a good rationale around why you think it’s good or bad, not just your point of view for point of view’s sake. It’s a lot of things, but it all adds up into a level of maturity and respect for the discipline of product design, both engineering, business, and again, design.

Larry: No, that’s a really good point. It leads me into another question that I have for you because you know this talks about how to get in the door and get noticed, and I love the advice of: live and breathe the product that you’re going to be going in and interviewing to work on, to show that you care about it, you’ve thought about it, show the way that you think, how you collaborate. I think a lot of what you are saying also applies to people moving up in an organization. And so I’m curious about your thoughts in terms of who are the people that you tend to promote. What do you look for in people that you’re moving up into senior designer, managers, leads, that type of thing? The kind of things that may have served you well as an entry level designer aren’t necessarily going to translate into being a leader and a manager, and so that’s a different type of skill set. Right?

Mike: One, to get noticed you need to have artifact out there: Behance, Dribbble, your own website, it doesn’t matter. I use that portfolio of work and your holistic view of yourself as a designer as a way of bringing people in. And then, to get in, you have to really give tangible, real world examples of how you’ve encountered something, not theories and aspirations. Then, when you’re in, I’m looking for someone who, on first days, tries to figure out, “How do I deliver value almost immediately?” Part of it, and I’ve experienced this myself, and I’ve seen others suffer from it, is you won’t get the respect of your peers until you actually generate that work product. And you show that you can actually go a tight loop around from design to delivery. That makes everyone feel good, and now once you’ve built confidence around you, it’s about being consistent. Now let’s talk about what manifests in that exercise. One, you know, the human side, do you have a good design sense? Can you be customer based? Two, can you rationalize that with the business goals? And can you re-frame the problem so you help make the business goal attainable without sacrificing what is good for the user? And then the third is can you partner with engineering to make it happen? I believe that the real chemistry in a product organization is between a designer and the developers. I think historically they talk about the tension between design and engineering, and I think that’s foolish. If you see that as tension, you are perhaps eliminating and looking down upon the catalyst for change within the product. The more you bring them with you the better it is. And once you get that partner in crime from the developer standpoint, then you can do extraordinary things. And then there’s communication. You have to be able to tell a big-picture story. I have a lot of designers who love to work in Sketch, and that’s their communication medium. And it’s like, you know what, sometimes you’ve got to put a deck together. I like to think of it, and I’ve done this throughout my career, is, I have a passion for comics and animation and storytelling, and so the more you can tell a very human story about what you’re doing — arguably a pitch deck — the more you get senior executives nodding their heads, and you don’t need spreadsheets, it doesn’t have to be your words, it’s just so obvious. There’s a great Steve Martin quote that someone asked him, ”How did you become so successful?” because he was, at the time, a really off-beat comedian — not traditional. And he says “You’re so good, that they can’t ignore you.” And that’s what this is about. You tell such a good story that they can’t ignore it. They can’t then just get to the spreadsheet, or get to executives using executive judgment over things that they really have no idea about. But being able to be in that environment, telling a good story… And then the last piece, is emotion. You have to bring emotion to the work you do. You have to bring passion to it. The problem is that passion is easily squashed by the technical, by the business, and even by the design side, because “Hey, you need to follow our patterns.” Remember that?

Larry: Yep.

Mike:   The reality is you have to bring the emotion to make the leap. But at the same time you have to do the basics very well. Oftentimes designers try to design everything at a 10, or an 11, and you have to take a portfolio approach. And what I mean by that is you have to have a diverse approach. You have to put bets on those things that you think will be true delighters and differentiators. And that means you have to bring and point your emotion at the most important things, and the other things, get them good enough. And then with that, when you are in crit, or when you are getting feedback, you can’t ever be defensive. Being defensive is meaning that you are almost in a fight or flight state. And that means that you are triggered that anyone is questioning your concept. And once, you can again, trust and let your guard down, you can take all manner of feedback and work with it and facilitate it. Oftentimes, and I mentioned the example of dying on the hill, often designers will die on that hill at that moment, and they’ll go down with their design. And the reality is that design is change over time. You will be able to perhaps get that design through, but you’ll have to make some trade-offs along the way. And oftentimes people just don’t understand the big picture yet, and they’re coming with the wrong mental model. So that’s the power of the story deck — you tell the story of your product — so you help diffuse people’s mental models of what they think the answer is, and then you just keep going with them. There’s, I think, a Taoist line, is that trees break in the wind, while grass bends and flows, and that’s sort of where you want to go — you want to flow. You want to be able to be flexible, knowing that it’s not lost, it’s never lost.

Larry: Yeah, that’s a great point. I think people often lose sight of the fact that if you’re going to win a war, that means you have to lose a few battles.

Mike: Yeah.

Larry: I think that’s a fantastic point. I think that does differentiate designers who are at a more junior level from people who are going to advance to that next level. That they see the big picture, and they are willing to make concessions because they can see that there is a bigger win that they could have, versus fighting for every – single – pixel, and then losing the war (which happens sometimes). That’s a really good insight.

So I know we’re almost out of time, there’s just one more question. This is, if you could go back in time — don’t we all wish we could — and you could talk to young Mike, as he’s just starting out, what advice would you give yourself?

Mike: One, I’d just go straight to design. And I’d reflect on what I was naturally good at, and where my aptitude was. I just didn’t know it existed. But I wasn’t willing to reflect and inspect what I had enjoyed in high school. The other is sometimes you just have to tough it through. Sometimes you have to do the nasty hard stuff to get to the good stuff. I did not have a long term mindset. I was an “in the moment” guy. And part of that allowed me to explore a lot of things. So I guess for me it would have been to have more of a balance. To understand that hacking the system doesn’t mean that you just ignore the system. Hacking the system is working within the structure, gaming it so you get and benefit from it, and you get what you need out of your education. And I sorta did that later, when I walked in through the side doors. I just didn’t have the GPA to qualify me for a lot of the post-graduate work that I really was geared to do. That’s what I should have been doing, but I wasn’t able and willing to pay attention and pay my dues to get there.

Larry: Fantastic. Well, thank you again. Again folks, this is Mike Tschudy. He’s the Head of Design for, and if you are a designer looking for a great opportunity, I’m sure Mike is always hiring.

Mike: We have a job opening!

Larry: I knew it! Thank you, Mike. I really appreciate your time.

Mike: Thank you, Larry.