Frontline Manager at Meta to Senior Director at Snapchat in 3 Years (Career Story)

0:00No matter what happens, you should never fire the first 15 engineers in the company. This is Rong Yan. He grew from a frontline manager at Facebook to a senior director at Snapchat in three years and shared everything he learned along the way. A very critical cultural philosophy I learned from Facebook is that everyone who worked on engineering need to be technical. At Snapchat, he shared interesting learnings working with the founder and CEO. Evan has a really high bar for performance. And it reminds me of Steve Jobs. Part of his growth was from job hopping to a director role at Square. And then you were thrust into a director role.

0:35What were the biggest gaps that you saw? There's a lot of gaps. But the biggest gap I saw... Here's the full episode.

0:45I'd like to go into one of the first legs of your career, which is when you joined Facebook. What is the story behind you joining Facebook? Yeah, so I think that's an interesting story. My career path is a little bit non-traditional. I was a PhD. I used to be a research world for more than eight years. So, and because after I graduated, I spent five years in PhD program and then I spent another three years in IBM as a research scientist, mostly focused on computer vision and machine learning, right? And then I started to realize industrial research model like IBM research or Microsoft research with this kind or 50 % mix between research and engineering, it's probably not going to be sustainable.

1:26I have to choose either 100 % on research or 100 % on engineering, one way or the others. So that's why that was back in the year of like 2009, I started to reflect on that. Then I started to question myself, okay, which path I should go? There are three paths in front of me. One is that I can be a faculty in some school. In fact, I do an interview with some path of school at that time. or I can be a coin developer or coin trader in a financial engineering firm. I also have offers from some of the top quantitative trading firms or I go to a software engineering company like Facebook. So when I was thinking deeper, first I wanted to be software engineers.

2:09I think that's the way that you can creating some things that was influenced more people than just doing trading. The second thing is that I want to go to places that can make engineering to be the first-class citizens. I think in the financial world, engineering is always a second class. It's not a first class. I can be a faculty, but being a faculty, I think the impact is smaller because you can only impact the scale of a school or maybe the community, but not the entire world. So that's why that was the years I make up my mind that I want to be in the software engineering world. And if I want to be a software engineering world, I want to join a company that are fast-growing and have the potential to influence a lot of people.

2:54And I think Facebook, it is the one that fits with my criteria. So that's why I'm lucky enough to be part of a Facebook during their fast-growing years, like in the early 29th. So I think at Facebook, you transitioned into management. and I think the things in your career that I'm most interested in is at the subsequent two companies, at Square and at Snapchat, your career had explosive growth. Because at Square, I saw you were there for a little over a year and you went from a frontline manager to a director. Your team was around 40 plus engineers. So I'm kind of curious to dig into how you got that opportunity and how that growth came?

3:40Yeah, I'll be very transparent here. In fact, when I joined Square, I was taking a director offer to join the Square. Oh, okay. So you signed up with a team that was already director size. Exactly. Yeah. And of course, Square is a smaller company. So that's why they are willing to give me the opportunity to perform at a director level. After I joined the company, when I started the team, it's about 25 people. And then I grow the teams into 50 plus people in a year before I left the company. So I indeed spend a lot of time to grow the machine learning teams and data science infrastructure teams like back in Square.

4:17I think it's actually a very helpful exercise. But one thing I do have to say that, and in fact, this is one of the lessons learned for myself, is that I do things like my transitions from managers to director teach me a lot of things. I start to learn a lot about the difference between line managers and directors and why they call it directors. So because director, it's about directing instead of managing. So it really opens my mind about what's the right way to managing managers instead of managing ICs. So you need to use a completely different philosophy to do that. And it takes me some time to adjust to it.

5:02But after this exercise, I think I've become a better manager at a different level. Yeah. I'm curious because your career grew so quickly that I wonder if there were any skill gaps. You went from a frontline manager and then you were thrust into a director role. What were the biggest gaps that you saw? Yep. So there's a lot of gaps, but the biggest gap I thought it's about back to the world directing. When I first step into the director role I actually don't understand the difference between director versus managers but when I start to practice it I start to realize like managing a manager requires a different set of skill because like typically the line managers are the one that knows the detail the best.

5:48unlike my Facebook experience I grow from IC to become a manager then I'm the one in the teams knows most of the details so that's why I continue I can continue to use that as the anchor points to managing other people because almost most the other people in my teams join after me so that's why I'm the senior people in the rooms but you start to go to a new environment you become the more junior people in the company but you're actually leading the more senior people in just in their tenures of the company, they are more senior, but you are leading them, and also they know more details than you, then what's the right way for me being a director positions to actually provide my values to those people?

6:34That's the most interesting part of it, because I don't think I do well in the first half a year, and once I don't do well, they may start to just feel like, okay, why do I actually need this layer at all? Because I'm not adding any values to their daily life. So, and that was the time I started to reflect is that if I'm becoming a middle layers between them and the higher level executive, what are the values that I should bring in for the organizations? So I think what you end up landing on, it will be about high-level thinking, about strategical directions, about the possibility that you can help to connect resource across different departments, about solving the most difficult problem for the organizations.

7:28It's all about those kinds of directions. And that's why it speaks to the difference between directing and managing. So it's no longer simply about managing people anymore. It's about directing an organization towards a better position in the future. So essentially, it means you need to operate at a very different level than what it used to be. So it takes me some time to understand. So the thing that took you from maybe underperforming initially to fitting into the director role was you stepped away from directly managing people and you thought more strategically about the group and that you were leading.

8:10Yeah, so that's totally the case. And also like put some more thought around what does your direct report was looking for from you. So, and there's definitely a reason why the original leader choose not to promote any of the existing leader into my role. Instead, they choose to hire another person into that role. There must be a reason behind that. And this means that there must be an area for improvement for them. As a leader myself, then I need to make it clear and then need to understand that, okay, what I can do to help to grow that person from their current levels to the next level. What's the missing pieces?

8:51Like what other thing I can help them? So, and when I start to understand that, that going back to my analogy of like comparing management to psychological doctors, right? So you start to understand what they are looking for. And then I will align my work towards that. And once you start to do that, you start to get more respect from those people because they understand that you are here to help them to grow to the next level. So, yeah, I think that's sort of a turning point for my director career. I can imagine that there's a psychological effect here. If someone gets hired a level above you, you know, maybe these people were hoping for that.

9:34Did you deal with any incidents like that? And how do you handle that kind of situation? So first, yeah, I definitely dealt with that. Because it's a human nature thing. Everyone wants to get promoted. And everyone will question why they are not the one that can promote it. So that's why the way to handle that is to really help them to understand that with me coming in, it's actually a much better situation for them in terms of their career instead of a negative. and in that case you need to find a common ground between you and your direct report. So you are not a blocker for that career instead, but you are actually a promoter for their career.

10:23And this is actually one thing I only realized half years after I become the director, to be honest. But after I do that, I think I'm doing much better in my following career in the future. Every single time when I go to new places, the number one thing I would do is to build a trust layer. And this is a place I really recommend a book called The Five Disfunctions of Teams. I think that book taught me a lot also. I mean, basically, the book, one of the key narratives for that book, it's about the most foundational layer for a successful team. It is trust. Everything building on top of trust. So that's the first things I would do is to build up a trust relationships with that person.

11:04So he needs to trust me that I'm here to help him. then I need to start to execute a few things to make him understand that. So, and also you need to help him to unblock some of the things that he can unblock himself. That also shows the value of you being an upper management to help your people. So I think that become a more and more important things like so for, for building a successful team. You mentioned that you were hired in as a director. So that makes me think about, let's say you are a really ambitious manager and you're thinking about how can you grow and level and there's the approach of staying somewhere, trying to get promoted, and then there's also job hopping.

11:48Do you think that job hopping is kind of the best way to jump up tiers as a manager? I never think about job hopping as the best way to jump up to the managers. In fact, even when I talk about Facebook, a lot of my OT members are already in a very high level. Some of my friends are already VP of Engineering in Facebook. So that's why I don't think job hopping is always the only way or the right way to do it. But I can speak to why I choose to do that. My philosophy is about North Star. I always have an all-star goal in my mind is that I want to become a CTO at some point for an AI company. You did it.

12:36Thank you. Yeah, so that has been an all-star goal even after I get my PhD degree for machine learning. I have been imagining at some point that AI can become a business by itself. But when I graduated, the world is not like that. I mean, AI is just always amplifiers. It's just like a component in a bigger company who can make the business better. That's interesting, but that's not the most interesting part of it. So that's why when I start to make up my mind that this is my North Star goal, then I want to make a plan out of it. my plan is that if I want to become a CTO I have a lot of weak link for that especially when I coming after my research career I know from being a research scientist to be a CTO there's a lot of gap so I recognize my gap it's about not understanding the industry how industry operate don't understanding infrastructure and back end don't understand front ends find products and don't understand like many other things.

13:46So that's why I need to choose my career to help me to fill in those gaps step by step. And in fact, here's a story. Before I joined Snapchat, I'm always a data and machine learning process. All of my position was related to data and machine learning. And when I joined Snapchat, there are two options in front of me. Either I choose to become the director of data or I choose to become director of camera, which is the first page of Snapchat. I intentionally choose to become the director of camera. And I need to learn about iOS and Android programming from scratch. I literally spent like two months learning about iOS programming.

14:23Again, I think this is a very unconventional choice because I believe most people will just let go with director of data because that's the most comfortable selection you can make. But my non-star is trying to become a CTO. I think in order to become a CTO, I need to understand product. I need to understand working with product managers and product designers. And arguably, if you just follow your traditional career progression within a company, it's really hard to do that. It's really hard to jump from a back-end team to a more product-facing team at that point. So I think that I should take that as a very great opportunity to challenge myself, to learn something different, and to inch towards what I'm looking for at the end.

15:08And I'm glad that I made that choice. In fact, the first two years in Snapchat, it's probably one of the happiest periods for my career because I really enjoyed that period. I'm learning new things. I find that myself was developing my knowledge base every single day. And that's the reason why I was choosing different things at different stages of my career. You worked in very different domains as an engineering leader. and I was curious, how much do the details of the teams that you manage matter? This is a very critical cultural philosophy I learned from Facebook. It's that everyone who works on engineering needs to be technical.

15:53I still remember the times that Facebook have this six-week bootcamp process. I don't know whether they still have it right now. So back in times, everyone needed to go into the six-week bootcamp process before they can choose a team. And I remember there's a VP level hires sitting right next to me. And she's just like doing the same thing as what I was doing, like finding bugs, fixing bugs, writing pull requests. She was doing that for six weeks. That actually shocks me because I come from IBM. Like IBM's VP never code anymore. I mean, I don't even, they probably only write PPTs at the end, I think.

16:27But this is one thing that was deeply planted in my heart afterwards is that I believe being technical, being detailed-driven, it's a very critical thing for us to success in the future. And that's also part of the reasons why I also love to get into detail these days. So I still write codes. I still review codes. Like right now, I at least write two or three pull requests every single week. I'm also the kind of person I'm not really good at speaking up if I don't know the details. I want to make sure that I understand the details so that I know I'm not making things up so that I can make the best strategic decisions for the teams.

17:08How do you find that balance though? Because even as an IC, there is some balance where you start to lower leverage tasks, you start offloading them to scale yourself, and you only take on the very critical things. I can't even imagine like as a CTO or director. what even detailed work is worth picking up? I think the best way to scale this is to always going back to your first principle. So at the beginning of every single week, I will ask myself, what are the top three things I need to achieve? Only focus on those top three things. And then everything else is less important. And sometimes one of those top three things will be development, getting the details.

17:53So I think that's a very critical part of it. So that's why I'm not saying that every single week you need to do the same things. But every single week, you need to have themes for your work. And you naturally understand how each theme is going to bring the best bang for the buck for your North Star goal. So that's why you keep recalibring yourself towards it. And I think this is the best way to scale. because like at the end, every people only have eight hour working time or maybe 10 or 12 working time every single day, but that's it. So you can't have more. I think the best people, not really just like spending more time, but they're really good at allocating their time and by understand the priority of each directions and spend the right time at each priority.

18:45I understand that Snapchat is in Los Angeles, which is very different from Silicon Valley. I'm curious, did you notice a big difference in the cultures in LA versus Silicon Valley? Yeah, so I think specific for Snapchat, the culture is actually very similar to Bay Area company. In fact, when I joined Snapchat, I found it surprisingly similar to Facebook's culture. It's moving fast places, break things, get things done, done is better than perfect. All those things apply to both Facebook and Snapchat. and partly because a lot of early people coming from Snapchat or working in Snapchat, they come from Bay Area or Seattle.

19:25So that's why like Snapchat has built a culture very similar to that. But broadly speaking, I think LA is a way more diverse space than Silicon Valley. I still remember like when I was living in Bay Area, I lived there for five, six years. Whenever I go to an event or a dinner, it's like you can find that like most of the topic people talk about on the dinner table, tech, stock, startups, the topics are almost always the same. So because that brings Bay Area to fame, but also means that a lot of people was working on the same things. But in Los Angeles, you get a very different vibe. You get access to a lot of different kinds of people.

20:04For example, in my neighborhood, one of my neighbors, it's a doctor, It's a medical doctor. And another neighbor, it's actually a cryptographer for Michael Jackson. I think I can never get access to those kind of people when I was back in San Francisco. It really helped you to broaden your views outside Silicon Valley. You start to understand that, oh, it turns out a lot of our people, a lot of our users are not just techie, are not just AI people. Instead, there's a lot of common persons who can still benefit from your product. And it helps you to put yourself into their shoes to understand how your product should be built in their cases.

20:48I saw your team grew to the size of 250 engineers at Snapchat. What drove that growth? I think we grew that organically in the sense that Snapchat became a bigger company over time. I remember when I first joined Snapchat, the whole company only had 100 people. I'm probably the 180th employee. And Snapchat grow into about 3000 employee in two years. So that's why like my team size also grew together with that overall company growth at the same time. Of course, there's a lot of efforts put into recruiting, like really shout out to the recruiting teams. I mean, a lot of efforts like to our interviewers for making that happen.

21:28But overall, I think like for a size of a company that was like tens of billion dollars, I think that's a reasonable size of a company that you want to build at that time. We do learn a lot from that process. And this is what I always call a painful period for fast growing. You will quickly realize the cultures that you want for a 100-people company is going to be very different from a culture for a 3 ,000-people company. You will see a lot of different sort of cultures start to clash with each other. in a good way. So that's why every single time when you double your team, you're almost like you're building a new company at that time.

22:12And this is the period that the leadership has to be very resilient and we need to be very adaptive to the new environment. Just cannot always just hold on to one thing to say, okay, I'm not going to change that. Like, in fact, that's different because we are building a very new company now. We are a very different company. We knew you used new way to think about the problems. So yeah, but that also really helped me to grow to seeing how you can grow a much smaller team to a much bigger team. What kind of a process you go through to make it happen. As a senior director at Snapchat, I imagine you might've had some proximity to Evan Spiegel.

22:48Do you have any stories working with him and what made him effective? We do have direct access to Evan. So in fact, I work pretty closely with Evan like for a few projects. I really like Evan as a leader. So in fact, the two things really strike my mind, like when you work with Evan. First, Evan has a really high bar for performance. So, and his bar is even at the pixel level, and it reminds me of Steve Jobs. So, and then basically, for example, in our product review, if we show him a demo, he will actually point out pixel level issues and ask us to fix. So that's why sometimes I would say that, okay, if we're building a demo, we say you need to build an ever ready demo, not a normal demo.

23:36But that really helped him to be very successful in terms of like building a great product. That's what he's really good at. Second thing is that I think he really cared about personal connections, especially with the engineers. Like he really kept his promise and he appreciated the value of engineering. So one thing I remember very clearly is that he actually told one of our leaders that no matter what happens, you should never fire the first 15 engineers in the company because they are the founding member for the company. Snapchat was started in a place that's called a blue house. It's actually a very small house back in Venice Beach.

24:18And then because the company is growing, expanding very quickly, so that's why they're no longer working in those small places. But after four years, I think it's 2017, like everyone bought the house back and then he started hosting the board meeting back in the house so you can see he's really deeply care about this kind of connections this like personal relationships and that also probably explained why he was trying to build snapchat and reach inherently it is a a tool that help people to build like more intimate connections and and and creating conversation with each other. So yeah, he's a really good person for that.

24:59You know, after you left Snapchat, I saw that you went to a series of startups. And now that you explain that you're overarching North Star, everything's now making sense. So now, at this point, it looks like you're starting to take on larger leadership roles at smaller and smaller companies. I'm kind of curious, how does the recruiting work at these levels? Yeah, I have to be honest on this one, maybe bragging a little bit, but I never look for a new job myself. I never look for new jobs proactively at least. So it's all coming inbound, like from either personal connections or like some recruiter outreach.

25:36And in most of the cases, I would prefer to go to a places that I actually have personal connection with. Because this is my fundamental belief. My fundamental belief is that no matter where I'm going to, I'm going to go through up cycle and down cycle. There will be a period the company do well, and there will be a period the company will not do well. And this is true for almost all companies I've been to, like Facebook and Square, Snapchat, and things like that. So I want to be not only I can grow with the company during the up cycle, but I also want to grow with the company during the down cycle.

26:15But in order to go through a down cycle, I want to work with persons that I like and I can think a lot with them so that we can all work together as a team to go through that. And that's why I really feel like personal connection is a big part of it for their decisions. And the reality is that it's a good time for engineering in the sense that I keep getting recruiting email almost every single week for different positions, but I ignore majority of those emails. But if things come through very personal connections, I value it way more. I find that that actually will be the more interesting part that can help me to excel in the long term.

27:01So that's why, yeah, this is basically my story. Yeah, overall, I think that also speaks to the fact that building a professional network, connections early, and it's a very useful exercise. So because you never know this kind of opportunity, when this kind of opportunity will come, but you want to capture that opportunity when it arrives. How do you compare the roles that come your way? Because when you're in a well-established ladder, you're a director, a director role comes, and you kind of decide on some. But let's say you're CTO of a certain company and you want to consider another leadership role at another smaller company.

27:41Is it number of people working there? Is it valuations? How do you make those calls? To be honest, I never take those two things into account. The valuations or the people report to me. I actually want less people to report to me right now. But it's all anchored against my North Star goal. So yeah, so maybe I bring that back before, but I want to bring this back to that also. I want to understand, is that choice actually helped me to move closer to what I want to do? I start to feel like this is getting more and more important in my career. Because the one thing I gradually realized, like when I was spending more time in the industries, I started to realize levels and titles, those are the things the company gives that to you.