Jaime Levy, Ux Strategist, Speaker and author of UX Strategy: Product Strategy Techniques for Devising Innovative Digital Solutions

available in 6 languages and now also on Audible

You can find Jaime on LinkedIn and on jaimelevy.com



Katty: I’ve been watching your career trajectory, and I was super excited to see that you had written a book, UX Strategy and that the audio version has just come out. So I wanted to have a conversation about you, about the book, and how you started your path.

One thing that I’ve noticed is this trend of reinvention with you from a designer to a strategist to an author to a public speaker to a professor, and how all of that’s going to come together for you. I just found that fascinating, so I’d love for you to talk about your origin story and what’s steps you’ve taken to come here.

Jaime: Let’s see. Well, I guess it started even before the browser when I was creating my floppy disk magazines, and I was a graduate student at NYU, and just really interested in nonlinear storytelling. 

And then trying to invent this new medium like it was just this total insane dreamer thing. And I guess because of the floppy disk I made, I actually finished it, and then I successfully brought the product to market by selling it. A floppy disk that opened into a HyperCard or Director presentation. I know for all the newbies, they’re like, “What are you talking about?” Don’t worry, you don’t need to know this old-school stuff. 

But you know it used to be really hard to make interactive presentations, but the upside of all of that was that you could be the first or you could do something that is only mediocre in design. But because it was the first it was like “yay.” 

That was how I started out. I was a horrible interface designer and a horrible coder. But I just kept pounding on these floppy disks, and then, the short version of it is Billy Idol bought one, and then it got launched as a commercial endeavor and then I got my gigs at EMI records and Viacom. And it all just kept going from there you know to eventually, doing an online magazine, and then getting a creative director role and just constantly working. 

I really believe that if you just keep working, and applying yourself, and learning new things, that eventually you’ll connect and get whatever it is that you want. Some job, or some gig, or an opportunity. And I think that relentlessness to persevere was something that has stayed with me, and I actually need to kind of manifest it now as I’m starting the next chapter of my career. 

Before UX, it was called interface design and then after interface design, then it was web design and then after web design, then we had information architecture and interaction design. And by the time I got back to LA after 9/11 and the dot com thing crashed in New York, as well as, San Francisco and LA, I came back here and it seemed at that point I needed to focus. 

And I should mention early on as a result of the (floppy) disk I was asked to be a part-time professor at NYU, and I did get flown around the country and the world, to speak at conferences, and I think like when you have that success when you start out you think that’s normal. And so for me, it’s just been catching up with my old normal, and it’s a curse and a blessing, and the blessing is obvious because you’re like, oh, I just want to continue to be a public speaker, I want to continue being known or recognized for my work. But the negative consequences, it’s an addiction, it’s like a high that you set here and you think, Oh, I always have to be at this level of an overachiever. And so, you know, in that sense I feel like I didn’t engage in my own personal life, you know because I sacrificed it for my career so much and didn’t really like relax into it until my 30s when I got back to Los Angeles.

Katty: Interesting. I saw you actually speak about it in one of your talks. I think was your Brazil talk about being an overachiever and what that means and constantly trying to do things, new things, or do things in a new way. I found that fascinating, it went through that same reinvention theme that I recognized in what you were talking about. So thanks for sharing that. So you mentioned, the new chapter, a new iteration of Jaime.

Jaime: New? It’s in progress. So, you know, I did my first book and I did really well with the first book. I was insane to write a book. That was so crazy. But I just felt like UX strategy was so interesting and even though nobody was paying me to write it, you certainly don’t make money off of the book. I just was like okay I’ll take a year and a half and spend my savings and write a book and sit in the library. And it was really rewarding. 

And so then when it came time to do a second edition, if I want to be current I did that. And I did it during the lockdown so that was kind of a good thing to do when you can’t really go teach in a classroom or go run workshops in a public space. But basically, my book is now out in the second edition and is being translated into languages, and I just found out it’s in German and Italian, and Portuguese this time, you know, on top of the other six languages and that’s really exciting. 

But the thing with the book is you need to promote it, and you know and you need to go do things to market it. Whenever you make anything whether it be a floppy disk or a website or an app or a book or you’re marketing yourself as a public speaker, it’s one thing that you do it, but the other half of it is in order to be successful, you just got to market yourself or your product. And it’s fine when I get paid to do growth design and markets and run experiments to market other people’s products. But I think, I’m kind of at least right now, I feel I’m just kind of over-marketing myself. All of a sudden I feel like, ah, can’t life just be simple again? Let me just get a job ideally as a UX strategist and, you know, and that’s it, let things quiet down. 

And so you can say it’s an existential post-midlife crisis, or maybe it’s a phase but I just had a job interview with a company that I hope I get, and they were telling me that they just had written an article related to this subject about so many people basically looking at their careers and saying, “Do I even want to do this?” 

I feel like COVID Hit the reset button for a ton of people and so now I’m less killing myself about, “Oh wow, I’m really not going to go crazy promoting this book because I don’t feel like it? Is there something wrong with me? Or is it just like maybe I just have to accept to let people read the book. I hope they like it.” And if people ask me to speak fine, but you know, I think it’s like at a certain point you have to say okay where’s friction and friction is trying to go tour and do workshops at what we hope might be the end of the pandemic but isn’t. You know, it’s like I suffered the same fate as people who, you know we’re in an orchestra, you know, or who had movies that came out. So I’m in great company of people who made their money by doing things for the public and in person and now that you know, there’s no UX conferences really planned. I’m speaking at the one in Estonia, one, this year, zero last year zero the year before, you know. So it makes you say what am I going to do now?

Katty: You’re right, it definitely has been a reset button on many fronts. We’ve seen this so much with so many other candidates that we work with who are re-evaluating “I’ve been doing XYZ until now, do I still want to do it, do I still want to live here?” Just really evaluating everything, but I totally hear you about the book because I also wrote a book during this pandemic. I had been working on it for three years, which was far too long but that’s just the length of time that it took. The circumstances where we found ourselves allowed me to finish it, so I am grateful for that. That was the silver lining in this crazy year and t it allowed me to finish it and get it out. But it’s just sitting there and it’s nowhere near where it needs to be… but it is what it is. It’s a story I needed to get out. I got it out. Now, if people find it, awesome, and if they don’t then we’ll cross that bridge. 

Jaime: What’s your book called?

Katty: It’s called The Butterfly Years, and it’s just my personal story dealing with grief and has nothing to do with Artisan Creative and it has everything to do with me. Obviously, as somebody who’s running a company, it is going to have to come to grips with having to manage grief and make that work otherwise it permeates everything.

Katty: If it helps people out there, it’s there. If somebody is going through it and they need to hear somebody else’s story who’s been in the same boat. Then I’ve done my job. 

Katty: Yeah, So when I heard that you had done your second edition and you had just done an audiobook. I thought you know I want to talk to her and see how that whole process was for her. 

Katty: Congratulations on your interview and I hope that it ends up being the right next thing.

Jaime: I hope so too. That would be great if my first interview turned into a job offer.

Katty: Putting out the good vibes.

Jaime: They were very surprised because it was a UX strategy position and I didn’t have anywhere in my portfolio that I wrote it. I didn’t want to say that I literally wrote the book on UX strategy because then they think oh she’s not humble or she’s too experienced so I didn’t mention it. They saw something in there and I’m like, “Oh yeah, I wrote a book kind of related to UX strategy.” and they’re like what’s it called, I’m like, UX Strategy. I can’t even own it. I can’t even own it, you know, I’m just like, ahh so shocking. Yeah, you know, I want the opportunity to practice what I preach. Enough, running around with the same lectures and enough training. 

I’ve done so much training in the last year, I think sometimes we just need to go back and forth and be okay with it. I’m not saying I’ll never do workshops again, I just need to take a break from that part of it or and pursue it. So yeah hopefully something will come up for me that is enjoyable. Because I think it’s important to have a job if you like and what I was shocked by when I looked at the job market this time was, oh my god there’s 8,624 UX jobs in this country and 30 or 40% of them are remote, and there’s actually jobs advertised for UX strategist title. It used to just be me and two other people. I don’t know if my book helped define the industry but it seems like when I read the job description, it had everything that I wrote about in my book so it’s a really exciting time that there’s so much opportunity out there.

Katty: Yeah, for sure. I’d love for you to maybe help define that a little bit, because obviously, we hear you know there’s on the design side of it, UX there’s XD. Now it’s customer experience, employee experience. Can you talk a little bit about that I know for just what I’ve heard you talk about before, it’s really the research and the strategy is the precursor before you even get into the design part of it. And I learned that thinking time is so important to be able to do that? Can you talk a little bit about that?

Katty: A little bit of both, actually.

Jaime: Sure. So I basically define UX strategy as the intersection between product design and business strategy. So business strategy is the top-level vision of an organization. How do we make money, who are our customers? You know business is defined, ultimately by their customers. 

So they have a vision and the vision might be a platform, multiple products, a suite of products, or one product. And then it’s like how do you really elevate that product, and bring it to market? So that when people have that first whiff of it, they’re like, smells awesome. And so when I started doing discovery phases back in 2008, 2009 for Schematic and for Huge, I really fell in love with it. Because I love doing competitive research. So interesting, I mean who doesn’t want to get paid to research the marketplace? And I loved the idea of finally getting to do user research. And so that was when I really became interested in it and realized that there was nothing out there that told us how to do it. I would just make things up as I went along and as I moved from different organizations, I would clean up my deliverables and take them to the next level. 

And then when Lean Startup came out–People don’t think of Lean Startup, as a product strategy methodology but I certainly do. It’s this idea to build the smallest version of your product, get it in front of your target customer, learn from it, whether it be an alpha or prototype, extract data from these learnings and learn from it, and then iterate. 

All of a sudden the discovery phase became not something like Waterfall; first, we do discovery, then we do the implementation, then we do usability testing and find out at the very end that not only does our product suck but nobody wants it. It was insane. And now all of a sudden, the discovery phase became something that can be iterative and cross into the implementation phase, and you can start building products and doing strategy, and testing it and validating it in much smaller loops all along the way. So that’s what’s really exciting is an opportunity to run some kind of experiments to knock out, to do rapid prototyping, to use whatever it is like sketch XD, other prototyping tools to get business concepts in front of the target users, and start doing user research that’s more focused on validating a value proposition, versus, you know, is this thing usable? Even if it’s really usable, but nobody wants it, then who cares if it’s usable, right?

Katty: Yep. Very good, and with plenty of products out there with great usability but they’re sitting on the shelf. I probably have a few of them.

Katty: Fantastic. You talked a little bit about this but I think, given where you are going, pivoting, and where you see the future to be for you at this juncture. What can you share with people who are either just starting out in their career path? And/or because of this past year, lost their positions, and they have to reinvent themselves. Where is it that you dig down deep to find that inspiration and that determination to just say you know what, this isn’t working, let me figure out where it is that I want to go?

Jaime: Yeah, I think just to be honest it’s very different for someone like me with two to three decades in the industry versus somebody who’s starting out. So I wouldn’t give someone the same advice I would give myself, there’s definitely different things going on. I can remember very well when I was starting out and the same feelings that I have now are similar. My dad gave me this great advice. When you’re looking for a job, or when you’re starting on your career, and when you interview with people, you want to be careful that you don’t have this flashing L on your head. Loser, loser, loser. 

Because people will spot this lack of confidence or low self-esteem, you know, and it doesn’t matter how successful you are, or have been, like me. Because you can still have low self-esteem or imposter syndrome, and so, it’s like you need to somehow put all of these fears of I suck;. I’m not gonna make it; I’m an imposter;I am so crazy that I thought I could do this film, to begin with. I’m too old or I’m too young or my portfolio doesn’t have X, X, X. 

I have to constantly work on this, to this minute, which is spinning a much more positive narrative in my head that, “No, no, I have something of value to give”. And then putting that negative energy into therapy, exercise, whatever you need to do to take care of yourself, but I still to this day, put it into how can I showcase my work, what’s missing? You know, look at my portfolio. Okay, it has all this but it’s missing, you know, this one deliverable. Well, I better make it, fake it till you make it, you know, and figure out a way to like get it in there. 

And the funny thing is is they may not even ask for it on that job interview, but if it’s like this thing that you think is missing, then it’s going to be flashing the L on your forehead and so to me, it’s like puffing yourself up and what is it going to do to make you confident for these interviews and if showing your portfolio and getting excited around the storytelling of your UX design which, it still is for me, then get that into your portfolio and any missing things.  Don’t spend eight hours a day looking for a job, spend four hours and the other four hours teaching yourself a new tool because there’s always going to be new things to learn. And if you’re not open to learning new things, up until, you know, your 50s and 60s, then whenever that is where you’re not open to new things, you better be at that last job that you’re going to station yourself at, because the industry, I promise you, just keeps on changing. You know it’s amazing.

Katty: Gosh. Great advice. I think for all levels of career and years in the industry and also not even to have to do with business. I think for anything where we tend to sometimes focus in on the thing we don’t have versus on the things that we do have it’s just such a great lesson to say you know what to say we have to reshift that mindset. 

There’s a great book that I read a couple of years ago by this woman called Sally Helgason, and it’s called How Women Rise, and she talks a lot about specifically women and how we get into this mindset of, oh, but you know what, let me work harder because I’m missing this 10% thing and not focus on the 90% that I have and it’s just crazy. I see it all the time. I see it, not just in candidates I see it in myself. And putting myself out for a conversation or a talk or something and if I don’t get it’s like, oh, that’s because I didn’t talk about this. You know what, maybe just wasn’t the right thing. So, yeah, great lesson. And I think also that that whole thing also speaks of desperation, and I think that that comes through, so loud and clear, it erodes the confidence that would naturally be there if somebody has worked on their craft.

Jaime: Yeah and we need to in this field of product design or research, ultimately we’re making something that we need to upsell, at the very end, even if it’s to our boss and say yeah this is awesome, you know, and it’s like, oh my gosh if we come to it from this place of fear, we’re never going to sell it.  So I think it’s easy to focus on the negatives for a lot of us, and we can’t afford to do that in our field because we’re always upselling our work.

Katty: Yeah. Have you ever taken the StrengthsFinder assessment? Have you ever done that? 

Jaime: No, I don’t even know what that is.

Katty: It’s similar to a DISC or Myers-Briggs. But it focuses on your strengths. The reason I like it, we do it for our company and we talk about our strengths all the time. Its created by Don Clifton, and is now as part of Gallup and it’s a personality assessment. The reason for him creating this was that he felt people focused on their weaknesses, and not on their strengths. The whole thing is about what are your top five strengths and let’s lead with your strengths and not focus on a thing that is number 30 something for you, let’s focus on the things that you’re really good at and then find someone else who your bottom five is their top five and then collaborate. So it sounds like it’s just human nature that we go there. If we could learn not to go there, it would be less, I think less of a headache for all of us.

Katty: Crazy. So, I know you’re teaching, you’re doing online courses, you mentioned that you’re doing a talk in Estonia. Are you doing that in person, are you doing that virtually? How are you managing your time and all the different places you need to be, or how did you manage your time and all the different places you need to be?

Jaime: Yeah, I don’t know how I’m managing my time right now yet. I’m still waiting to see where a bunch of things land. But the Estonia conference is the first onsite conference since COVID, since March of 2020. Well, basically there’s very few conferences in the beginning of the year for the first quarter anyway. 

So, anyway, it’s Web Usability Day I think is their legacy name. But it’s a one-day conference and then there’s workshops, three days prior to it. It’s in Estonia, it’s very affordable, it’s gonna bring in like a massive crowd of UX professionals. A lot of new ones but people mid-level and all over the place. And they’re coming from Estonia, but they’re also coming across the Baltic from Finland, and a couple of other Baltic states. So, I’m closing the conference, I guess I’m kind of headlining it, and then my workshop is one day right before that. So November 25th,iis my UX Strategy Workshop and then November 26th is the conference. It’s a Thursday, Friday, so but I’ll be in Berlin back in November, and then I’m doing a couple of talks, just private ones where I’m flying in. And then going back to Berlin and then I’m going to do this thing in Estonia. 

I am so over this idea of more online workshops. I think they’re a joke, sorry guys, but the whole point of conferences was to get people together physically in a space to network and touch base with other people and build relationships. And it seems I’ve done a bunch of these fake conferences, and it doesn’t feel the same, they never pay and it’s a joke. So I’m not into those anymore.  I’m really stoked that these people you know, the COVID cases are extremely low [in Estonia]. I’ve had my third vaccine. already so I’m totally going. I won’t be taking too much risk but definitely, I’m really excited to be around humans and doing my thing.

Katty: Yeah, humans, human connection. I’m traveling internationally for the first time since March of last year as well, and I’m going to Mexico and then to Dubai. But, I have to navigate the whole PCR test thing because I’m not going to be in the States for three days before I go so I got to figure that part out.

Jaime: Yeah. It’s a crazy time. I can’t believe really what happened. How much the pandemic just changed everything, it’s just, it’s shocking.

Katty: Are you seeing that in the world of products, are you seeing what’s happened with a pandemic impact, whether it be design thinking or about how people are approaching research. I would imagine that it’s changed how people are looking at how they go forward.

Jaime: Yeah well, everything’s online now. When I left Huge back in 2009, 2010. It was because I didn’t want to drive in my car in rush hour to agency land in Culver City, and I didn’t want to work in person, I wanted to work from home. So I’ve been working remote since 2010 and it’s not new to me, and Cisco Systems when I worked for them as a UX strategist, everybody was a remote workforce. So finally, the rest of the world is catching up with us and learning that it is possible, and even outside of product so I think it’s opening up opportunities in many ways. But, the negative consequence, and I felt this when I taught my last course at Claremont University, was that my students who were graduating, were just getting internships, but they’re online. 

At Facebook or wherever, and at any point in your life where you need human contact, and you need the nuance of someone kind of seeing that you’re confused, and you need mentoring or you need to get the confidence to ask for help, we need that to be in person. I feel like the people that are getting the worst end of the deal is the college graduates, the people who are just starting their career who have to start it by themselves in Zoom rooms. Hopefully, there’s going to be some way that it isn’t just this experience of online collaboration, because I just feel even when I had my second or third cat life of getting into the UX world, I can’t even imagine that I would have had the trust and camaraderie that I had with people at Schematic who came over and showed me how to wireframe when nobody was looking. So hopefully maybe there’s some way that people can reach out and have people to connect with for that kind of support since they can’t get it in person.

Katty: The whole mentoring piece of it. Yeah, taking somebody under your wing. It’s harder to do it this way. Yeah, you’re absolutely right. I have some nieces and nephews who started their first year in college last year. You’ve worked really hard to get into the school of your choice, but you don’t get a chance to really experience that. So now as a sophomore, they’re getting to experience it for the first time because now some other classes are in person. So really interesting to kind of watch this new generation of those who are starting and those who are graduating, it’s just a very different world, for sure.

Jaime: Yeah it’s crazy. It’s really crazy and maybe five years from now we’ll look back on that and go, Oh man, it was so great, why didn’t we just do all that remote work and it was so easy. But it is weird, I just got off the phone with a client and he’s just saying that he’s not leaving the house and he doesn’t want to get the vaccine because he almost died from a vaccine from something else a long time ago, so he’s just like staying in his house for his whole life. And I just, I feel in our field where we’re designing products for customers and users, it’s like, “Nah, we need to have human contact and get out there.” When I’m feeling really low, I reach out to a friend and I have to dump, and say “Ugh”, and have them tell me. I just hope we don’t lose everything as a result of this, online world that we live in now.

Katty: I don’t think so. I mean I certainly hope not. I do feel that there’s a hybrid version of it that’s going to be more pronounced. I mean we went to such an extreme this past year, I do think there’s going to be a hybrid world in front of us. I haven’t quite figured it out yet, but little by little I think we’ll fall into place. Let’s end on a couple of inspiration pieces. Where do you get your inspiration?

Jaime: My inspiration now is probably– I consume a lot of film. I like to have a big impact. I actually went to the movie theater, on Sunday, by myself, bought a ticket to go see Ich bin dein Mensch, I’m Your Man, a German film about a man robot who was built to learn on what a woman wants and then they program him to be the perfect partner. It was amusing, to walk into it, to have it open up and see all of Mitte Berlin and see the TV tower and see the food and see inside the flat. I miss Berlin so much right now, I felt like when I got out of there  I had just gone to Berlin. It just reminded me of all these tiny little things. So I get a lot of inspiration from being able to transport myself into different realities physically and through film, and right now, traveling is limited,but I definitely get my inspiration from seeing other cultures, other ways to live. 

I lived in Berlin for most of the pandemic, and it took months, but after being there and away from here for so many months it really– when you experience other cultures, it makes you appreciate and also find things you don’t like about your own culture. But I feel like having perspective is what inspires me.

Katty: Love that, and for creativity to bloom, do you need that spark of inspiration for creativity to happen, or is there another thing you tap into when you sit down to write or to do another wireframe or to create, what would you tap into for that?

Jaime: I don’t know, I wish I could answer that. I don’t know. I spend my days at the computer then I go and walk on a trail. It’s extremely important for me to get out and walk in nature and I do that every day and I listen to the same 3 podcasts. The New York Times Day thing, The Berlin Briefing, and then Doug Rushkoff’s Team Human And that stuff, while I’m like in nature and walking around listening to these podcasts, again, I guess I feel transported and I feel immersed. I think that when I leave the house, and when I come back, whether I’m jogging or listening to music and weird experimental atonal music that nobody would like unless they’re into weird music. That helps me really reset the crazy stuff we’re telling ourselves in our head or just like being in a mundane moment. I think sitting at a computer for more than four hours, not healthy for me.


Katty: I love that. Both for creativity and inspiration, it’s not going to happen nine to five necessarily looking at a little screen. To be able to get out of this and just get other influences. I find nature so healing in so many ways and my ideation just goes off the roof when I’m out and about.

Jaime: Where do you go, where do you get your nature? 

Katty: My favorite place is Point Doom in Malibu. It’s a very easy little hike, but you are at eye level of the pelicans flying by. It’s just the most incredible sensation sitting there and you see these majestic birds flying right at your eye level. So whenever I can, whether it’s a birthday or an anniversary or something special, that’s where I like to go. 


Jaime: Nice. Yeah.


Katty: Well Jamie where can people find you?


Jaime: People can find me on LinkedIn, @Jaimerlevy. I’m on Twitter, I’m not tweeting so much. I was told I need to get on Instagram but I’m like, “What?”. And then Jaimelevy.com and then the book userexperiencestrategy.com. I’d love to just mention if people don’t like to go walk in nature. I recorded my audible book at this great studio in the valley, where I grew up, and it’s me reading my book and doing some impressions of myself, and it’s a lot of stories and so far the reviews have been really favorable. And so if you’re not a big reader like me I hate it, I don’t really like reading. I can read an article but long-format, not so good. Check out my audible book if you’re not sure go to userexperiencestrategy.com and listen to the first two chapters and try it on. But I’m really excited about the audible, you know for my book I self-produced it, paid for it, and it’s mine. So that was important to me, you know.