Hello Jasmine. Can you tell us a little about yourself?
I have one “shocker” fun fact that I pull out in interviews and awkward icebreakers: I was born at home. My parents paid the midwife forty bucks and half a pig for the delivery and — as it later came out — it may have been only twenty bucks.
The reason I bring this up is obviously for a few giggles, but for me: it’s important to remember where I came from, which was not from much. I was born in a one-bedroom shack in northern Wisconsin with insulation coming out of the walls. My parents were residual hippies, and for my entire childhood, my dad’s work history was spotty. My mom was a stay-at-home mom for most of her life — an amazing and incredible undertaking — but the scenario didn’t do much for propelling career aspirations.
When I talk about growing up with very little, I’m also very conscious of the privilege granted to me based sheerly on the lightness of my skin. I had access to reasonable education, and I was generally looked upon positively; opportunities were possible for me and trouble didn’t find me. This doesn’t mean that my journey has been easy.
I often remind myself that I’ve worked very hard to move beyond the low expectations that were set for me, which at minimum was making more than my parents and going to college. I never in my wildest dreams thought I would or could be much more than a school teacher. Don’t get me wrong, teachers have the most difficult jobs and are the some of the most driven, kind and caring people I know. I’ve seen the incredible impact of teachers and administrators and school leaders during my time working in education.
It was just that being a teacher was really the only profession that seemed viable to me based on what I was observing in the careers of women around me. I am incredibly grateful for my journey, particularly to the people who lifted me up along the way and served as exemplars for me to be inspired by and aspire to. There’s definitely some “from poverty to tech” story in here that I have yet to write, but that’s for another time.
Let’s go through your design journey. How did it all start?
I went to a very small Christian school in the midwest for junior high and high school. I was co-valedictorian, with an equal GPA to my best friend. She and I are still to this day super tight, and I love our paths. We were both “good” at everything and got to dabble in everything from volleyball and basketball to drama and choir and all the typical extracurriculars. We were both in accelerated calculus, getting As in science, and taking basic art classes. When we went off to college, she started her journey to med school, and I started mine to design, although I didn’t know it at the time.
I started off as an undeclared liberal arts major at Iowa State University and breezed through a year of Calculus I and first-year science classes. The second semester I enrolled in Calc II and was plugging along, assuming I would head into some engineering role, based on my older brother pursuing mechanical engineering at the time. I really wanted to take an art class though, so I met with an advisor at the design school. She frankly told me that I couldn’t enroll in even a drawing class without enrolling in a design program, so I said, “sign me up for Graphic Design!”
I learned that there was an entry year of classes before you actually applied for the program, so I spent my second year of school taking all of the first year art classes and taking Ancient Greek to fill the time my first year of classes had provided the gaps for. One of my early claims to fame was having translated the first chapter of Homer’s Iliad, and it was pretty cool to read ancient Greek scrolls when I studied abroad in Italy, but alas, the skill is gone.
When did you fully switch to design?
I got accepted into the graphic design program and earned a presidential scholarship that year based on my portfolio. I was pretty proud of the work I was doing, but I was still going through the motions without much purpose or tenacity. At one point, I chose to study abroad with a class of graphic designers instead of investing in an internship.
I graduated top of my class. I had an excellent portfolio. But I had zero hustle, and I thought things were going to be handed to me on a platter. I moved to San Francisco after school in 2002 and couldn’t get a job. The odds weren’t in my favor; the whole city was reeling from layoffs of the dot-com bust, but I can’t say I tried very hard. I was a meek little girl from Iowa who had yet to learn how to stand up for herself and internalize her own value.
I did side projects and interviewed here and there, but always prioritized paying rent over pushing for a desirable and fitting career. Things changed when I had had enough at my pay-the-bills job: managing a few small branches at Enterprise Rent-a-Car (that’s a rabbit hole we won’t go down).
Six years into my role, I applied an evaluative criteria I had put together to use every six months or so to determine whether I should stay or leave. The criteria were based around compensation, quality of life, and fulfillment. I usually had one or two of them at a time, but at this point, I found myself with none, and I bounced.
I headed back to school, this time to the Academy of Art (where I later taught), and stumbled through a graduate program in graphic design. I remember nearly crying touring the graphic design floor before I signed on. I had missed typography and texture and color so much. I missed looking at street signs and getting an eye twitch from bad kerning. I knew that I was back on my path, and I was determined to make the experience into something.
Grad school was hard, one of the life things that nearly broke me. I was still paying off undergrad loans and was broke, and had to work to pay rent while paying exorbitant tuition. I was never the best in class, but I was developing a finer sense of me and my special skill sets. I ended up delivering the school’s first digital thesis project: an app on budgeting, which was nuts — and frankly risky — in a primarily print department. And that project got me my first job as a UX designer.
How did you get to Intercom from Facebook? Can you walk us through the process?
Backing up a tiny bit, I worked for a year and a half during grad school at Office, a graphic design studio in San Francisco, and that was the extent of my career as a graphic designer. My first job out of school was as a UX designer at an agency, which was a leap for me since I’d only done that one UX-related project for my thesis (talk about the hiring manager seeing the potential and having confidence that she could groom me!). I joined Facebook when that agency, Hot Studio, was acquired, and I acclimated quickly to Facebook because I came in with both the visual design chops from school and newly developed UX skills from Hot.
I made it almost five years at Facebook and led design on some pretty cool stuff, notably Payments in Messenger and Safety Check. For the last two years, I worked on a non-core Facebook project called the Summit Learning Platform, which is a partnership between Summit Public Schools and Facebook, where we supported the development of a personalized learning platform for K12 students in Summit Public Schools and program schools across the country.
This project and team was really a departure for me from Facebook as I knew it, and notably, a turning point where I identified that I preferred solving tough social and system problems over flashy consumer-facing design work, which has stayed true to my next few moves, all the way through Intercom.
My decision to leave Facebook and move to Chan Zuckerberg Initiative (CZI) was a pretty simple one: the Summit Learning Platform project moved over to CZI, and I decided to quit Facebook to continue working on the project. The move of the work made a lot of sense; CZI wasn’t around when the project kicked off initially, and once the organization had momentum, CZI’s philanthropic mission of equity of education was a much better fit than Facebook’s mission of bringing the world closer together.
For me, I made the decision within what feels like minutes: I care deeply about education and was incredibly invested in the work. Plus, there were no designers yet at CZI, and the idea of building a cross-functional design team from scratch was compelling.
I technically only worked at CZI for 16 days. I was on a “shut down” team at Facebook charged with making sure the project and team wrapped up in an efficient and tidy manner. So while most of my teammates who also made the personal decision to join CZI became employees within a few months, I stayed on at Facebook for nearly six months to ensure the transition was smooth. Meanwhile, I was building the new team at CZI, getting operations in place, hiring teammates, and building the cultural foundation.
It was almost a fluke that I moved on to Udacity. I was on LinkedIn constantly recruiting and reviewing résumés for CZI, including a director role we had open ourselves. Udacity also had a director of design role open. I think at one point, LinkedIn was just like, “hey, we see you looking at similar roles, how would you like this one that’s exactly what you’ve been doing?”
I had two opposing thoughts: first was that it was out of my reach. I was leveled as a product designer — Facebook is a pretty flat organization without “senior” or “junior” titles, and CZI was modeled similarly — and I was at what I believe they’re calling “Staff Product Designer” now, one level above senior, but I wasn’t at a director level. Pushing aside the self-doubt, I scoured the job description and let the other thought come through: I can do this.
I applied with a “why not?” attitude, and soon got an interview screen and then another one, and then an onsite interview. I got the job offer within a few days, and I decided to take it: it was a company focused on chipping away at the difficulty of education access, following many of the project-based learning principles and self-directions that were tenets of Summit Learning. But at Udacity, I could flex more of my growing leadership skills and uplevel and upskill a team. For me, that meant more potential impact on students, indirectly.
That was a scary moment for me, leaving the comfortable fold of two companies that had been run very similarly, and really stepping out on my own. I was the top design leader at Udacity, and the responsibility and influence required were totally different not only at my new level but also without the infrastructure that both Facebook and CZI had built and maintained for smooth operations. I was ready for a challenge. I was prepared to grow.
I stayed at Udacity for a year, and it was full of ups and downs. Much of it was fantastic, and much of it was painful. I had a really amazing team and got experience leading not only product designers, but also user researchers, design systems engineers, and design program managers. The skill and investment of my team members are incredible, and I’m really proud of both their efforts and impact. I won’t dig too much into what made it so challenging, but what I will say is this: every company has their shit, either externally or internally. What you have to decide personally is if that shit is the kind of shit you can deal with, and in the best scenarios, that shit is composed of the kind of challenges that actually give you energy, that you thrive on getting into. Towards the end of my tenure, I very quickly realized that for me personally, the challenges that Udacity was facing were contributing neither to my energy, nor my growth.
I made a very quick but thoughtful decision to leave and actually gave notice before I had another role locked down. I interviewed with Intercom and received an offer shortly after, and it was a fairly quick acceptance on my part. One of the best things all of my experiences — including Udacity — has given me is a crisp sense of what I need in my role and what I want to steer clear of. In the few talks I had with my now-boss, Paul Adams, he frequently mentioned how over the course of building Intercom, they were able to use the patterns of what worked in people’s previous jobs, but also create anti-patterns for the things that didn’t work.
It summed up quite succinctly exactly how I was profiling and processing the search for my new role.
Something I’ve been reflecting on lately is how organic my career path has been: an acquisition and a project moving required little job searching from me and really just a supporting does of intentionality. I was counting the other day, and I think I’ve actually only interviewed six or seven times, and all but one of them (that I can recall) resulted in offers.
I’d like to think it’s because I’m a superb interviewee, but I actually just haven’t interviewed that much, and when I do, it’s been very targeted. On this last round, I did entertain a number of casual calls, but only chose to move forward if I was fairly positive that the role would both meet the criteria I had crafted and that I could have a substantial impact.
Intercom seemed to meet nearly everything I was looking for: in addition to an interesting problem space, being led by not only design-sympathetic but also design-experienced leaders and execs, having firm but flexible principles, running solid operations, exemplifying kindness and care towards teammates, caring about diversity, and so much more.
What is your favorite project that you worked on?
I’ll always have a soft spot in my heart for Safety Check at Facebook. This was a side project for me; I was working on Payments at the time. One of the Payments product managers had participated in a hackathon supporting an engineer, Petter Cottle, who had some curiosities based on the Boston Marathon bombing. Namely, in these sort of panic-ridden events like natural disasters and terrorist attacks, could Facebook do some good by using people’s connections to relieve worries by broadcasting their safety?
I saw the hackathon output via our Payments PM, Sharon Zeng and immediately said, “you need a designer on this.” We started whiteboarding, thinking through privacy, how emotionally charged these scenarios were, and the expansiveness of connections, and we informally kicked off right then and there.
There were a handful of designers who popped in and out of the project, including Carla Ablaza Echevarria and Cameron Wu, and a number of researchers and content strategists who all ran it through to launch. And it’s been wildly successful.
It’s one of those things you never want to see triggered, but when you do, you have confidence that you can confirm the whereabouts of your loved ones. We’ve seen this used in terrorist attacks and school shootings… man, such awful, horrendous events, but I take solace in knowing that it brings comfort to many in these terrible incidents.
Looking back, would you do anything differently?
Yeah, I’d take visible and accurate credit for my work. This was one of those projects where we did the work, and others got the credit. I remember being in an internal design all hands when the project was launched, and my boss couldn’t make the meeting, so she was like, you take this. Our VP of design stood up to announce product launches, and as I was waiting for my moment to speak, he instead credited the team where the project had recently been moved to as its permanent home.
I was shaking, furious. I tried as calmly as I could to gesture for the mic, and with my voice shaking, credited and thanked Carla and Cameron and the other folks who had really made this happen, but I was pissed. The new owning team had done some polish work, but we had brought this thing to life and worked painstakingly on it in our free time. It just goes to show how important it is to make yourself visible — especially as a female — to get your efforts recognized.
Believe it or not, this happened again. They moved the project to yet another team, and Fast Company did another write up about social good at Facebook, and they targeted the new design manager as the face of the project. I didn’t think too much about it until my manager came to me and sympathetically apologized, telling me it was a better PR story. It was cool, I got my name as a contributor, but the perceived story was more important than the real one. I guess it’s just politics and PR, but it was really hurtful.
I learned a lot from this experience though; I probably over-credit when speaking about my team or the people I collaborate with. I want people to know that I see them and their efforts and I want those looking at me to know who they actually should be looking at.
What’s your Design Team’s tool stack and what are the key decision factors when choosing a new tool?
Most of the teams I’ve worked on and led have had a similar set of skill values, despite being named differently. I’ll use the Facebook model because it’s really well thought through (and was similar to what we developed at Udacity). The design skills Facebook values are product thinking, interaction design, and visual design, and there are associated tools for all of these.
For the product thinking piece, your tools are really your team, your collaboration and communication, and your documentation. I really can’t emphasize enough the importance of a collaborative word doc like Google Docs. When you’re establishing strategy and process, defining the problem to be solved, determining success metrics, collecting the landscape — this is all stuff designers do or collaborate on — it’s so important that it’s accessible to everyone on the project. Features like links and indexes and comments really open up the space to collaborate with anyone from a fellow designer to peers in product and engineering to company leaders. And so much of great design work is in a pre-interaction and visual design phase that it’d be negligent not to call out this as a tool.
The other two skills — interaction design and visual design — have a much more obvious tool stack: Sketch (or Figma, which my team at Intercom invests in), InVision, Framer (or Origami Studio), etc. I personally went through the switch at Facebook when we moved from Photoshop to Sketch and was one of the last adopters. I was frankly super fast at Photoshop and didn’t want to convert until I had to. The learning curve for me paired with the necessary conversion of files wasn’t immediately worth the time, but eventually, I caved.
I think of that experience frequently anytime someone comes up with a new tool idea and consider the following: first, does it bring significantly more value, and second, how disruptive will this be? I’ve said “no” or “not yet” to a lot of tool requests, always considering value, compatibility into other tools, integration into workflows, budget, etc. I also can tell you if I get frequent and unnecessary spam emails from the marketing team of a new tool, it’d be a hard sell.
At Udacity, the team was super interested in Framer X, which I’m guessing they’ll adopt once stability sets in. We also introduced Notion as a tool for user research reporting (lesson learned here that while it’s an excellent tool, at a company-level you really need to actively drive adoption to make it useful). There’s a handful of others that are were brought to my attention, including Mural, which we used for research synthesis for our remote research team.
Have you ever been involved in building a Design System? What was the process behind it?
I was really incredibly proud of the design system at Udacity. The team leader and manager, Jennie Yip, led and developed the whole thing nearly singlehandedly. She’s a hybrid engineer and designer who started off on the dev marketing team and pitched and implemented the system. She brought her first teammate on board, and in the past year, the two have developed and launched a rigorous comprehensive system of elements and components.
Jennie’s amazing; she’s motivated, self-driven and deliberate and required so little of me… it makes her accomplishments so incredible. Building a system is one thing, but driving socialization and adoption is another beast, and she’s really nailed it in whole.
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How do you approach successful work with front-end developers?
When I started in product design at Facebook, I admittedly hadn’t worked a lot with software engineers. Coming from an agency, I either had passed design work off to an in-house development team or worked more in exploratory engagements. I knew I’d have to build good relationships at Facebook and learn quickly, so I developed early habits of treating engineers as design partners. I’ve had countless developers sit beside me and painstakingly explain why something is or isn’t feasible, and I’ve sat beside the same number to account for quality execution.
It’s not to say engineers and I don’t always see eye to eye; I can think of a number of developers that I’ve gone head to head with, but it’s all in the spirit of problem-solving, and I firmly believe multiple people with different skill sets can more efficiently and effectively solve a problem than an individual in isolation. If I were to give advice on how to successfully work with engineers, I’d recommend building a relationship above anything else. If you trust your teammates and value their skill sets — and they value you-you can get past just about anything.
How do you come up with new ideas/approaches to design?
I tend to approach every problem in the same way, doesn’t matter if it’s a design project or a staffing challenge or a strategy attempt. I always make sure we have a defined problem (what are we trying to solve), determine if it’s an actual problem (how do we know this is a problem), uncover the landscape (how has this been solved before), determine scope and implications (when do we need results by and what are the consequences of time and resources), define metrics (how will we know if we’re successful), and so on.
I’m skipping over a lot here, but it’s essentially applying a development and design process to anything. I’m a firm believer that new and innovative solutions or approaches don’t come from thin air, but rather are cultivated from thorough understanding and exploration.
One last thing: Who inspires you the most in the design world?
Honestly, I probably look up to my husband the most. He and I are often polar opposites in many respects: for example, he’s self-taught, and I’m over-educated. He always has a handful of side projects going on like apps, blog posts, speaking, and so forth; he gets his energy from side projects. We started dating when we were both working at Facebook — and mind you, meeting at Facebook is different than meeting on Facebook — and he immediately inspired me. He’s really the reason I started writing about design. We join forces here and there for side projects every now and then. He also taught me to ask “why.” At first, I thought it was endearing, his endless questioning: This guy wants to know about me! He wants to know every bit and piece. And then I realized curiosity is core to who he is, and he’s instilled curiosity in me, which makes me a better designer and design leader.
I’ve also been incredibly fortunate to have great mentors in my career, particularly women. In fact, all of my first managers at Hot Studio and Facebook were female. I realize that isn’t a common experience, and knowing that pushed me soak in their knowledge and experience as best I could.
There’s something indispensable about having people pave the way for you that are in some ways like you. And I’ve been able to craft and hone my leadership style around those who were exemplars for me. From Margaret Stewart, I learned that authenticity and genuine care and investment in people leads to great relationships that lead to great outcomes. Maria Giudice taught me to push boundaries over conformity, and that while you can’t win everything, you can be intentional and impactful. Elizabeth Laraki taught me pace and evenness, and that life is about a lot more than work. These women are all powerhouses, and I value each of them so much. Their love, kindness, support, and faith in me has propelled me to where I am today. Sounds cheesy, but it’s true! And for me, these mentors have inspired me to be not just a great product leader, but a great people leader. I am and always will invest in my teams before myself, and even before our products, because performing and happy teammates are the biggest lever to building great products.
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