Office Hours: I'm Chief of Staff to the CTO at Roblox and previously led engineering teams at Quora. I'm Jessie Duan.Featured

Hi everyone! I’m Jessie Duan, Chief of Staff to the CTO at Roblox. Prior to Roblox, I was an engineering manager at Quora. I’m also particularly interested in computer science exposure - I cofounded Code.X ( a nonprofit to empower high school students through computer science and design thinking, and Girls Teaching Girls To Code ( to introduce high school girls to computer science. I have a bachelor’s degree in applied mathematics and master’s degree in computer science from Stanford. In my free time you can find me searching for my next paragliding launch site. Ask me anything about technical leadership, engineering management, teaching computer science, and more!
Thanks so much for joining us @jessieduan!Elphas – please ask @jessieduan your questions before Friday, June 11th. @jessieduan may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
Hi Jessie - What a fun company to work for - my sons are huge fans and would love to know what you love the most working for Roblox? What are the "must do" initiatives that you focus on to continue to grow your career?
So glad to hear! What I love about working here is how much everyone genuinely cares about the Roblox community. We have a company value of “Respect the Community”, which basically means: the Roblox Community comes before the Company, which comes before the Team, which comes before the Individual. Some of our engineers today got started by building on Roblox, so maybe one day your sons could work here too ;)In terms of growing my career - I'm learning so much in my role every day. I actually keep a log where I write down key learnings each week - things I could've done better, how a decision got made, how someone asked the right questions to surface a key issue, etc. I also talk to peers outside of the company - I don't do this in as organized a way as some folks do, but especially in a CoS role I like to stay aware of what other roles are like.
@jessieduan Jessie, in your experience, what are the best ways for product people to work with engineering teams; how can/do Engineering managers influence that collaboration?Thanks for taking time to engage with the community!Silvia
I have a non-answer :) I think it depends on the needs of the team and the existing culture. I see the PM and EM as partners who work together to ensure the team is healthy and delivering towards the company vision. Each has their own core roles, but there is often a lot of whitespace and give-and-take depending on the people and the team needs. I've seen EMs very involved in the product and roadmap, as well as EMs who are pure people managers. So my best advice is to build a strong relationship with the PM / EM, have difficult conversations as needed, and work as a team.
What led you to pursue a Chief of Staff role? What do you hope to do after?
I’ve always been very curious, and I’ve liked exploring and doing a lot of different things. I also have a tendency to see things and want to fix them! And on top of that, I really admire my CTO and have so much to learn from him. All of this made the role appealing. That said, I’ve really missed being hands-on, and sometimes I’ve wished I was more technical, so I’m thinking about going back to a more hands-on role in engineering afterwards. Long-term I'd like to be in a leadership role in engineering, and it's especially important to me to be able to inspire other young women.
Hey, Jessie! Chief of Staff varies tremendously between companies (special projects, internal ops, extension of your exec, etc). How have you scoped your role to stay aligned with your interests?
Great question! From the very beginning I've worked very closely with my CTO, who has been awesome and intentional about shaping the role for me and my career growth. In our initial conversations we talked about the rough breakdown of my role as mainly focused on special projects, as well as some day-to-day execution. Now we just continually adjust - for example, one thing we're trying to be intentional about is getting me exposure to technology projects, in addition to people projects.I will say - although I’m a big believer in being intentional, I’m finding that I’m exposed to a TON in this role that I wouldn’t have thought about previously. Being open to anything that needs doing, rather than sticking too closely to what I think I like, has continued to shape my interests.
I love this idea of having a general framework while leaving space to adjust to business needs. I'm in the midst of transitioning to CoS at my current company, so this is super helpful! Thanks!
Good luck! CoS is definitely an adventure. Feel free to DM me if there’s anything I can help with :)
Hi Jessie, i have so many questions for you. I am currently building a startup where we believe in the positive force of gaming. I think gaming is a key into engineering for girls, because it is basically applied science in a fun way. Since now you are at Roblox how do you see diversity evolving there ? Would love to meet you? Are girls as resilient as boys for example, or do they quit faster? Warm regards, Heidi
Hello @jessieduan Thanks for taking the time to uplift and help with your insights.What strategies do you suggest for increasing presence of women in SW engineering (both from company and prospective employee perspective)
Hi @jessieduan! Thanks for taking the time- I'm in a doctoral program at UCLA studying how authentic computing experiences in the elementary school classroom can impact equitable outcomes in CS for girls and students of color. What tips do you have to encourage girls and students of color to pursue CS as an interest potential career path?
Sounds like you're doing some very cool work! Personally, I am totally fine if someone explores CS and doesn't find it interesting enough to pursue. But what pains me is when someone has a series of bad experiences or misconceptions and doesn't pursue CS, when they may have really enjoyed it otherwise.So my tips for someone supporting girls and students of color are:1. Make sure the act of building is fun. So many people gravitate towards CS because they love the magic of creation and seeing results. Help students hang on to this.2. Share the wide range of things that computer science can be used for. Sometimes students are more excited about the applications - the ability to build tools for education, for healthcare, for cryptography, etc. The results are very tangible.3. Build supportive communities of peers. If there are older students who can mentor younger ones, even better. Especially when getting to coding, 90% of it really is debugging, which can feel really hard because it's repeated failure (errors, etc) before you find success. Having a supportive community is so helpful.4. Bring in role models. There are a lot of stereotypes about what it means to be a "coder", and what roles computer science can open up. Break them!
YES to ALL of this! I couldn't agree more. I appreciate your response- it's really pushed me to think about my research and my role as an educator!
Hey @jessieduan I was browsing the Office Hours post and found yours - my kids LOVE Roblox. It has helped my 11yo daughter embrace her love of STEM and coding. She has earned thousands of Robux (as I refused to pay real-world money when she could earn then herself) by building Obbies and worlds (I don't know the terminology, she'll be so embarrassed by me RN). Thank you for giving all kids and creators a space to bring their creations to life! During the pandemic (we're in Victoria, Australia, the most locked down place on Earth) Roblox provided my kids with a safe space to socialise online. It was (and remains) a key place my kids meet up with their IRL friends.
Are there any aspects of being Chief of Staff that surprised you once you got the job? Do you have any advice for someone approaching it from a program management background?
The biggest surprise for me was really how much imposter syndrome I felt. I have so much opportunity to make impact in this role. By nature, I also like to solve problems I see. But in this role, I see many more problems, and harder problems to solve. I kept getting caught up in: Why can’t I do more? Why can’t I solve these big, hairy problems?The reality is that hard problems are often hard for many reasons. The Chief of Staff role is a special one in that often you have so much opportunity, and you get to tackle harder problems than you would otherwise. It can also feel less rewarding because some of these problems take months or years to really see change and see impact, versus a project that launches within a quarter.The beauty of all of is that I’m pushing my limits and understanding what those limits even are. My abilities limit me, not the opportunities or the role. But I’ve really had to learn to be much, much kinder to myself along the way.
Hi Jessie! You have had such an interesting career in STEM education. I'm an informal STEM learning professional who thinks a lot about equity and educational systems. My question is - what do you think is the biggest barrier for getting more girls and women into computer science, and how might we address it?
Hi Sarah! I really think it really comes down to stereotypes and community. Unfortunately this permeates pretty much every stage - from childhood to college to early career and onwards. There are so many stereotypes about who is good at math and science, and what computer science even is. This affects how girls, especially early on, think of themselves. It also affects how adults encourage kids. This book is a little old now, but had a really detailed explanation of a lot of this dynamic: I really think it’s about education - having role models show the cool things they work on, and how computer science is a tool that can be used in pretty much any sector (education, healthcare, etc) rather than a black box.In college and early career, I think community becomes a bigger factor. This means peers who you can work on projects with, and who can share opportunities and tips on getting started - they don’t have to all be female, but do need to be supportive. This also means role models and mentors who can continue to inspire and sponsor younger folks. I can still name many of the women who were 1-2 years above me in college - I wasn't that close to many of them, but just seeing them gave me inspiration that I could do it too. And personally, I've been hugely impacted by people who have gone out of their way to encourage me (I was ready to leave computer science after my first class!) and give me opportunities, and I certainly wouldn't be in my role now without people believing in me and vouching for me. So this really comes down to older folks reaching out, and all of us supporting these communities.
Wow, thank you for such a fantastic answer, Jessie! I'm definitely going to check that book out - thanks for the recommendation. It's interesting to see how these dynamics permeate layers of education and career. I work a lot with organizations (mostly nonprofits) that are trying to make a difference with STEM equity and am interested in how for-profit companies are working on this issue too, beyond just internal HR/hiring practices. If you get a chance to read back over these comments, I'd love to know - Are there any organizations (for profit or non profit) that you think are doing the work really well? Anyways, thanks again!
Hi @jessieduan!I'm building a startup in the AI space and I'd love to know your thoughts on upskilling software engineers in AI. Have you seen much interest (from both the perspective of employers & engineering employees) in AI/ML upskilling?
Hi JessieWhat a great initiative on your part! This is actually perfect timing as I had been wondering who to turn to about this. You see I have a 17 y.o. step daughter who wants to become a Doctor. She has been accepted to the university of her choice for a bachelor of science. She doesn’t have much knowledge of technology, and needs for learn more about the computational aspect of science and the role it plays in medicine. Would you know what avenues she can explore for this? Thanks for your help!
Congrats to her! If she’s in university then that's perfect - I’d recommend that she take an introductory computer science course to start with. It would give some foundations in computing, although likely wouldn't be specific to medicine. If there are any electives or courses about computational biology that could give some exposure, that might be great to look into.
Thank you Jessie! Great suggestions, which I will pass onto her
Super excited to meet you! My son's a huge Roblox fan, and I'll earn a lot of points with him for saying I've e-met you :)
Tell him I say hi :)
Tell us more about paragliding!!
I started paragliding a couple years ago and am now officially obsessed! Flying is just a magical feeling - it’s so peaceful and quiet to float through the air, no motor and no distractions. And it's surprisingly easy to take off - you start on a hill, bring up the wing, and take a few running steps. Then you rely on “lift” (aka rising air) to keep you up in the air. My favorite place to fly is along the coast near San Francisco, where you can easily stay up for hours. Here’s a shot:
wow I definitely need to try! staying up for a few hours sounds so dreamy. im assuming you are in a harness and kind of "sitting"? do you try to navigate? or just enjoy the views? I'm guessing it's kind of meditative and you just chill? Unless I'm totally misunderstanding and it's actually very athletic?
Do it!!! Yup, on the coast you're sitting in a harness, chilling, and flying with birds. It's freaking awesome. The most athletic part is probably hiking to launch if it isn't a drive-up launch. There are some places, like the mountains, where the air is more turbulent so you have to work harder (mostly mentally) to stay up... but I love the chill aspect!
Hi @jessieduan! Thanks for taking the time- I'm in a doctoral program at UCLA studying how authentic computing experiences in the elementary school classroom can impact equitable outcomes in CS for girls and students of color. What tips do you have to encourage girls and students of color to pursue CS as an interest potential career path?