“Being Generous with Knowledge” — with Kim O’Rourke, Head of UX Writing at Lyft

Today, we’re speaking to Kim O’Rourke, Head of UX Writing at Lyft. We discuss her early days at Facebook and Pinterest, how she fell in love with UX writing, and the exciting work she does at Lyft.

Today’s episode of Journey Map is brought to you by MindManager.

Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

Transcript:
Welcome to Journey Map, the audio experience that deconstructs the career paths taken by some of the world’s most interesting people. Today’s guest graduated from UC Davis with a bachelors in English and Music. After graduation she went on to work as a Customer Service Representative at Kforce Inc. In April 2007 she set off and started working in User Operations at Facebook where she stayed for five years before becoming UX writing lead and content strategist at Pinterest. Where she helped concept, develop, and rollout Pinterest’s very first ad campaign in the US. In 2018 she leaves Pinterest to become Head of UX Writing and Content Strategy for ride share app Lyft. There she’s headed many exciting projects.

Today’s episode of Journey Map is brought to you by MindManager. Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

DH: Today we’re speaking with Kim O’Rourke, Head of UX Writing at Lyft. Kim, welcome to Journey Map!

KO: Thank you Dave, that was an awesome intro.

DH: Hey it’s your life so don’t give credit to the messenger in this case. I am so excited for the discussion largely because as I was saying before we start the recording you know just given companies you’ve worked for and specifically that your career background is in UX, that hits pretty close to home for me so I’m very excited. Where I want to start is you went to school for english and music, so I’m interested in learning more about what the decision looked like from high school to say this is where I’m going to go in my higher education. Then how did you go from feeling that way in highschool and this is the path I want to take, to then jumping into the world that you’re now in?

KO: Yeah that’s a great question. The path to my english and music degree is a really strange one, and also a sort of unintentional one. So I actually had the honor of receiving a memorial scholarship from my high school during the graduation ceremony because I’ve been studying piano and most of my youth, and this scholarship was to honor a student from my high school who passed away in a car accident several years before and she was very musically talented and gifted. So this scholarship that I received sort of set me on a path in college, that honestly I don’t know that I had planned to study music in college, but I really wanted to use a scholarship to honor the school and the family who gifted it to me. So that is what set me on the path to study music and that ended up being my minor in college. Then english is much less of a clear path there, I honestly I didn’t know what I wanted to do in college I was an undeclared major at UCDavis until my winter quarter of my sophomore year, and the school was like Kim you need to declare something. I had taken a number of English classes and that was always my favorite subject in high school, and so it was just like this seems like as good a path as any since I don’t really know what I want to do, so that’s how I landed there. When you’re in college and all your family and friends are like “What are you studying? Oh english do you want to be a teacher?” and I’d be like “I guess” I didn’t really know what I was going to do with this degree. So I didn’t have a plan necessarily, and after graduation I ended up at Kforce which is like a staffing firm and I just was using my skills in customer support that I had learned from like my coffee shop gig in college to sort of translate to an office environment there.

DH: So an interesting background, which makes sense in terms of how you went from your higher education at UCDavis into that job at Kforce. I guess it seems like a big leap and I don’t mean that in a rude way, but it seems like a big leap into this job at Facebook and we can touch on that a little bit as well. How does that look? How do you go from working at Kforce, a staffing agency, to taking a seemingly important job at Facebook in terms as a User Operations Analyst initially?

KO: Yeah that’s such a good question. In all of my jobs I have been lucky enough to just know someone, even the Kforce job one of my best friends from college who graduated before me was working there, so that’s how I kind of got my foot in the door there. I knew that Kforce wasn’t like the long term place for me, and it definitely was an entry level. One of my best friends from high school had just gotten a job at Facebook in what was then called customer support and she and I had been obsessed with Facebook in college. So Facebook had started in our sophomore year of college I think around then and she and I were very active early users, back when there was no news feed and you were just updating your profile and checking your friends accounts. So we were some of the earliest users and fan girls of the site. When she started working there I just was like oh sign me up, so it definitely was a bit of a leap but back then I was still so junior in my career and she was just excited about being there and excited about the work that she was doing. She is one of my favorite people that it was a no brainer for me to interview there. It was also just an entry level job in the customer support team and it was growing really rapidly at the time Facebook was still college students only and scaling pretty quickly. The way that the company was tackling scaling at the time was just like throwing bodies at the problem so that was a great opportunity for me to jump into a department that was growing really fast. I grew in my time at Facebook as the company grew and opened up to users beyond students there were more and more challenges that we needed to tackle. So it was a really cool place to grow up as a new person in the workforce, I eventually got to try my hand at all kinds of different work including reviewing abusive content on the site, helping reduce spam, and working with engineers to keep people’s accounts safe. Eventually I got to move into a Manager role, managing people who were doing the same kind of work that I was doing. It was just a really great place to grow up as someone who was new to work and certainly new to tech.

DH: When you leave Facebook to go to Pinterest and what I didn’t say in the introduction is that you were also a founding employee there. So how do you define founding employee? Were you in the first 10? The first 50? The first 3? What does founding employee mean to you?

KO: I was lucky enough to be the 25th employee at Pinterest. So Pinterest is like again every job I’ve ever gotten it’s luckily because I knew someone, and my dad always says that that’s how he got every job he ever got too it’s like you know people and get these amazing networks and you want to follow smart people and the same thing that happened to me at Pinterest. I don’t know if this is too much backstory but Ben Silverman who is the CEO of Pinterest his wife and I worked together at Facebook and that she was actually the HR person who onboarded me during my first week at Facebook. When Pinterest started it was an invite only site at the time, she introduced it to me and several other Facebook employees, and we all were again early users, and super obsessed with the site. I was such a big Pinterest and that was like my dream beyond Facebook, it was like if I were to leave Facebook my dream place to work would be Pinterest. So I was able to send my resume along through her, I interviewed there, and I actually started out there in community opportunities which is similar to customer support. So I was doing the same kind of work that I was doing at Facebook, but for Pinterest when we were still really small. What was so great about being an early employee there was we were all in a one room office in Palo Alto, the site was still so young that it would go down all the time so you know we would all be like “Oh my god, the site’s down what do we do!?” and you could just literally holler across the room to get people to jump on the problem. Pinterest was probably my favourite place I’ve ever worked, it was such a special time to be there, it’s such a special company full of really smart low ego individuals who care about the user experience so deeply. So yeah that was my transition to Pinterest, and I’m happy to go more in transitioning into UX writing there.

DH: Yeah, I’ve read that you said “While UX writing was my bread and butter at Pinterest I got to dabble in all kinds of writing including Pinterest’s very first ad campaign in the US, the ‘What if’ campaign focused on vulnerable moments people face in their lives from the everyday to the epic. We showed how Pinterest can help you reimagine these risks as possibilities”. So maybe walk us through both like how you got into that UX writing role and maybe even define what UX writing is or means to you. Then also what was the transition like getting onto the team that worked on this campaign?

KO: Pinterest is a company that really early on invested in the discipline of writing and they hired their very first writer who’s this amazing woman and mentor of mine named Tiffani Jones Brown and she started the writing team at Pinterest. She was the original writer so she was doing everything, she was working in the product itself, she was doing blog posts, emails and communications, she was working on internal writing helping to develop our mission statement and company values. Now as she started to grow her writing team I was in a lot of meetings with her, and I was like what is this content strategy writing work that she’s doing? I’ve never heard of this in a tech company and I want to learn more. So I took her out to coffee and she was so generous with her knowledge and she shared all these resources for me to sort of scratch my itch learning about content strategy and what it meant to be a content strategist and writer in tech. I ended up because at the time I was still in community operations, I ended up using the resources that she provided me to do a rewrite of Pinterests help center. Then I was like this is a super fun project, I got feedback from her and I was like “What would it take for me to join your team?” and of course she’s such an amazing woman she was like “ You’ve already proved yourself let’s just make it happen!”. So that’s when I joined the writing team and I started to focus on UX writing, which because of my operations background and my familiarity with the products of Pinterest and how users thought about it and how they experienced it it just made a lot of sense to continue on that path. I would describe UX writing as the partners to product designers, who are these user experience experts who are working in the app or web itself. So I get to be the person who helps to make screens, flows and systems that’s as understandable for users as possible from a word and writing perspective. But what was really cool about the writing team at Pinterest was that it was a team made up of people like me who were product writers, as well as brand writers, more classic copy writers, business writers, and we were all on one team together and we all got to critique each other’s work, and help each other with projects, and as I said dabble in all kinds of different writing. So when Pinterest was getting ready to make its first ad campaign in the US there was a cross disciplinary group of us that got together to work on this. We decided to produce this ad campaign in house instead of working with an agency, so I got to be on it along with my coworker Mac who is an amazing brand writer, then we also had three amazing designers Morgan, Tim, and Jeremy. We all concepted this idea, so it was a lot of post-it notes in a room like what do we want to showcase in this campaign? What is the heart of Pinterest? What’s the brand of Pinterest? How do we want this to come to life? Since so many people use Pinterest to discover things they love that they never knew they cared about. So they have these transformative moments with Pinterest and we really wanted to showcase that part of it, and how people love to try things on Pinterest and they feel empowered to do so even if it’s something they’ve never tried before. So that’s the kind of story we wanted to tell in our ad campaign which we called “What if?”. We showcased people getting their first tattoo and saying “What if I don’t regret it?”, or people getting bangs. You know things that are small risks but Pinterest helped turn them into it every day little wins.

DH: Yeah we’re gonna include a link in the show notes where people can see the campaign in action since it is really cool and trying to describe it in words over an audio podcast is difficult. But definitely will include that link so that people can check out the finished product, it’s really great work. So you know I was unaware of your really personal connection to getting your job at Pinterest, in the first place so it must seem like for you to leave and migrate to the current job you’re in at Lyft must have been a pretty big draw to get you to leave Pinterest. Can you walk us through how you made that decision and why?

KO: Yeah actually it’s a funny path too. I was at Pinterest for over 6 years and there came a moment where I thought it’s time for me to leave. I love the company so much but I was ready to strike out on my own and try something different. In sort of a best laid plans way, I had actually planned on maybe doing some of my own consulting and freelance work. But this opportunity came up with Lyft and what I loved about the opportunity was that Lyft hadn’t really invested much in the discipline of UX writing. There was one amazing writer there who was working in product but lived on the marketing team. So when they opened up this role, it was just like I can see here that I can prove to myself that I could prove to myself all the work I had learned at Pinterest I could prove to myself here that I could do it again. I could prove to myself that I could help build a discipline in a way that Tiffani did at Pinterest. So it was kind of like I just wanted to see if I could do it. When I joined Lyft and it was just the two of us building the discipline from the ground up it was a total firehose of work because the company was close to 3000 people when I joined, and just two UX writers for the whole product. So it’s just been a really cool experience of teaching both people in our department who we work with really closely what our world is and how to work with us. Beyond the people we work with day-to-day, teaching others at the company the value of the work we do and how we protect the Lyft brand inside the product. So I guess to more directly answer your question the draw for me was I want to build this discipline from the ground up, I want to see what it would be like to do that myself.

DH: Well I mean that sounds like an exciting proposition in terms of why you would do it. So what has it been like, because you have succeeded in doing it. So what has it been like going from this two person team to where you are now?

KO: It’s been amazing! like I said right at the beginning it was total firehose of work there was two of us supporting something like 30 plus designers, like each of us were supporting that many designers. What was so great was when people started to see on the projects they were like “ Oh my god! It’s so much better to have writers on my projects, they’re better, they’re clearer, they’re better received by users” it was not a hard sell to then say hey we really need to grow our team because we could be working on so many more things if we were a bit bigger. So in less than a year we tripled there’s now six of us including myself working in all parts of the product, and honestly we could probably double and still have enough work to go around.

DH: Wow, that’s exciting. Well listened to this other podcast (no paid sponsorship) called Business War, it’s probably my favourite podcast actually other than this one of course. I just got a notification literally 30 minutes before we recorded this interview that a new season of Business Wars is available for Lyft vs. Uber. So when you think about the discipline of UX writing at Lyft versus what you see at your core competitor at Uber. What do you think are some of the differences, or what are some of the things you have tried to really bring to the table or to the product to differentiate?

KO: Man it’s tough, I mean Uber clearly has an excellent you UX writing team as well. I know that they’ve invested in the discipline and I applaud them for that. The things that we’re always trying to do at Lyft, I mean Lyft has always been such a friendly human first brand and that’s always been the case, and it comes out in our brand work that you might see in the world, the ads, the marketing spots that you might see. As a UX writing team our goal was always to infuse that brand into the product where it made sense to but also just keep the app as easy and simple to use as possible. I don’t know if that’s a super great answer dave but that’s the best I can give on the one.

DH: No I think that was totally fair, and it was a very blunt question and I don’t normally ask questions like that on the show either but it was just so timely I had to.

KO: Yeah, I’m going to have to listen to that podcast business wars for suure.

DH: It’s funny I actually heard about it from the Tim Ferris podcast, he said there was a season about the WWE vs. the WCW, and I wasn’t like a big wrestling fan but he went on about it for five minutes explaining how the audio quality was great and all this kind of stuff. And it really is the audio engineering is superb, so I’m hooked and there are 30 something seasons and their not short season, anyway I digress. If you were to look at your career including higher ed on an emotional timeline, there’s highs and there’s lows, what has been the lowest point for you and what’s the story you can wrap around that?

KO: The lowest point was probably around the end of my time at Facebook. You know user operations was such an amazing discipline to grow up in, it’s a great way to get to know how to work in tech, it’s a great way to get to know the users that your serving, and the company that you’re working at, and for me it was a great way to learn how rto become a manager and what that meant. But I also knew at my core that itt wasn’t the long term discipline for me. It didn’t always make me feel strong in my work, and they always say you should find work where you’re playing to your strengths, and it gets you excited to come into work everyday and I didn’t feel like it was checking all those boxes for me. I did the same kind of work at Pinterest and had like a rejuvenation of it, where at least if I’m doing this work I’m doin git at this new company that I’m super excited about and there was like a breath of fresh air there. So yeah, I would say tha’s the lowest point for me was the end of my time at Facebook.

DH: Well thanks for sharing that. If you were to take that same timeline and extend it out five or ten years, what do you hope will be the new high point in the future?

KO: It might have been obvious when I was talking about it, but the high point I’ve had already was finding the discipline of UX writing for the companies that I work for. It’s like I’ve finally found the thing that speaks to me and the thing that I’m super excited about. If I play it out the place that I think my heart is going now is like how do I help people who are interested in UX writing, which is a relatively new discipline so how do I help more people transition to it, or learn about it. Similar to the way that Tiffani was so generous with her knowledge during my days at Pinterest, and told me all about what the discipline meant to her, I want to be like that for other people and pay it forward. So if I were able to do that in a more official capacity or just reach more and more people I think that would be the next high in my career.

DH: Well we will start with our audience on our podcast today, there we go. There’s a lot of people who I know are early on in their business career,design career, marketing career that’s kind of our three main buckets of listeners we cover and so I think you shared some really great stories, and messages to them in terms of how you’ve been able to get to where you are. So again thank you so much for joining us today and we will include a bunch of links to where people can learn more about you and the projects you’ve worked on in the show notes. It’s an exciting time I’m sure to be in the space that you’re in meaning the last few months, but in general an exciting time. Again thank you so much and yeah as I say to all of our guests I hope we can do this again in a few years to see if you reached your emotional high.

KO: Yeah thanks Dave, thanks for being such a good moderator and question asker!