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Being a First Time Exec at an Early Stage Startup
A conversation with Jean Hsu, VP of Engineering, Range
This week I talked with Jean Hsu, VP of Engineering at Range, a company that helps make teamwork way less work. We spoke about being a first time exec, how she navigated being a mother and exec during a pandemic and what she enjoys about early stage startups.
This interview has been lightly edited for length and clarity.
So we met speaking on the same panel.
Yeah. It was about challenging the default performance management systems that companies have, and we got those mugs with our faces on them, which was amazing. My partner loves it. He's like, "Oh, then I can use it and then you're just there with me," which is very sweet. It feels weird to use a mug with your own face on it.
It was a very thoughtful gift. Can you give us a quick tour of your background and how you got into tech?
I think on the West Coast there's a lot of people who are like, "Oh, I've always wanted to work in tech. I always wanted to start a startup." My path was different. I did take some computer science classes in high school and then I lost my way in college a little bit, where I was like, "Oh, maybe I'll do chemistry." I have some family members who are in medicine, and so there was a very heavy pre-med pressure, stuff like all the pre-med requirements, and then was trying to decide my major and then realized there wasn't really anything I enjoyed as much as this intro CS course that I had picked up again my sophomore year.
I scrambled to get all the prereqs done and ended up majoring in computer science, but I didn't have any idea of what that would lead to. I graduated in 2008. My parents didn't really have a lot of context about the tech industry or tech companies and they were pretty concerned that I wouldn't have a job, that all the jobs would get outsourced. And so that, I think, has been eye-opening for them of like, oh, I did all right.
Then I ended up at Google, which my parents knew of. On the East Coast…a lot of the people from my school either ended up in finance and consulting or some of these big companies, right, and so I don't think I knew of any startups. I didn't even know what startups were. I moved out to San Francisco to start at Google Mountain View after an internship, and then I was really only at Google for about a year and a half and I started to wonder what else was out there. A big company like that can be pretty insular. They keep you in this bubble and, yeah, your social interactions, your food, all your basic needs are met.
Lunch is provided on campus, so there's no need to leave.
Right, yeah. I'd eat, I'd eat breakfast, lunch, sometimes dinner. I'd go and play ultimate Frisbee with all Google people on their field. Well, I think I was just curious what else was out there and I quit without really knowing what I was going to do next. Then I spent the next few months picking up Android development, started working with a small startup called Pulse, which later became LinkedIn Pulse, which became the newsfeed of LinkedIn, worked there for about a year, but really fell in love with that early-stage startup environment. We were in Palo Alto, had a garage door. It was really very ideal startup life.
After Pulse I ended up at the Obvious Corporation, which we worked on a few prototypes. I worked on the initial prototype of Medium, which then became Medium, and the company became the Medium Corporation. That's where I really grew, I'd say, from mid-level engineer into engineering leader, with everything in between, senior engineer, tech lead, engineering manager, all the mixtures of those roles that you can imagine. I was there for five and a half years. I had had two kids during that time, and so was just juggling young children, commuting from East Bay to SF every day, very different life than we have now. Yeah, it was really hard.
So when I left Medium, I was pretty burnt out. I decided to go into coaching because I felt like that was a part of my job that I really enjoyed and it seemed like there weren't, at that time, a lot of coaches that also had the background of engineering leadership. I did some version of that for about three years. I got trained as a coach through CTI and built up a one-on-one coaching practice and then I joined forces with a co-founder and started Co Leadership, which is a leadership development company for engineers. We built out courses, workshops, ran a lot of in-person events at some well-known companies. We focused on that tech lead and first-time engineering manager experience of how can we support those people and move beyond their technical skills to how do you communicate well, how do you get buy-in, how do you find alignment with other team members or other teams?
How did your current role come about?
I'd been working on Co Leadership for maybe 2 - 2 1/2 years and, obviously, with the pandemic, we couldn't run in-person events, so that was challenging. Right around the pandemic and around that time, I really started to miss teams. I don't know if that's like I finally recovered from the burnout or what that meant, but I missed the experience of being on a team. Because coaching and workshops are very much you come in for some time and then you don't really have skin in the game, I guess, unless you take equity at companies or an advisor, and especially the workshops. It'd be two days with a group of 25 people and then maybe I never see them again.
They go away. You don’t work with them again.
Right. It's like, "Well, best of luck to you. I hope we've equipped you with some useful tools.” And, I think, at the time that I left Medium, that actually felt very appealing to me like oh, I don't really want to be entrenched in all the stuff. I want to be helpful where I can and then set some boundaries and be able to leave as well. Around that time, when Dan my previous manager at Medium, the co-founder and CEO of range, reached out to me, I was really missing being on a team, building something together, having that long-term investment, and then seeing how that plays out, giving people some feedback and then seeing how they show up in meetings or how they interact with other people.
You missed seeing the impact of your work.
Yeah. I also think, personally, for my career one thing that became clear to me was that I didn't want to be adjacent to the tech industry for the next decade in this training role. I wanted to be maybe in and out of it. I could see an ebb and flow of, oh, this startup or this opportunity seems really interesting, let me do that and follow through and build out the team or do that for three to five years or more. And then maybe, at some time, my kids are at a point where I want to be home more, I guess I'm home all the time, but I want to be more available to them, and so maybe I'll take some time and do a bit of coaching or leadership development work. But I think it became clear to me that I still wanted to be in it and come in and out of it for the next while.
How big is Range?
I think we're 12 right now and we're growing this year.Engineering is four full-time plus me and the CEO, who sometimes will scratch an itch and jump in as well, but, yeah, pretty small still.
This is your first time being a VP, right?
Yeah, absolutely. I had been a manager at Medium and managing teams, the publications team, and being the people manager for, I think, the most was 15 people, which I would say is maybe too much. The team itself at Range is smaller, so it's interesting how, in some ways, the role is very similar, but in some ways it's different too, right? The team is smaller, and so the people management is not ... it takes up less than managing 15 people.
I didn't really know what all entailed the VP role, so that's something I've been figuring out, and also figuring out that it is a Choose Your Own Adventure. It feels different, I think, for different people.
We don't really know what it means to lead in that capacity before we do it. What are some of the things that are different as a VP?
As a manager, even at a small company (Medium was not tiny, it was probably 160 people or so) it feels like the manager role is a bit more well-defined, whereas the VP role there were things I didn't maybe necessarily expect to be doing, but now that I see very squarely fall in a VP role like negotiating contracts with third-party vendors, there's a lot of compliance, reviewing policies, all these little nitty-gritty things, working with the founders on compensation modeling or annual review. We do an annual goal-setting process for people, so revamping that.
You get to zoom out a little bit and not be so just do the management role. I think, for me, I've been able to bring in a lot of the unique skills of my own interests and also skills that I developed in the last few years to do a bit of more community-building and, I guess, content marketing for engineering leaders. I spent the first few months at Range getting up to speed, supporting the team, but also learning the code base. I wanted to be able to contribute.
A few months in, I realized the gap I can help fill is really getting the word out more about Range, and in our target audience, which is engineering managers. I'm like, "Hey, I spend a lot of time selling things to engineering managers. Let me see how I can most effectively use those skills to engage with engineering leaders, provide them with useful content, and then uplift the brand to be thoughtful about engineering management so that people want Range to be a thought partner for their team when they think about how to manage remote teams and, yeah, what tools they want to bring in to help."
What does Range do for those who aren’t familiar?
At Range we build tools to help remote and hybrid teams work better together. At a high level, a lot of that is helping teams find the right balance between asynchronous work and synchronous work. So a large part of the Range product is fueled by these asynchronous check-ins. Instead of having a daily standup at a time that may not be convenient to people and people may not be listening and they just rattle off a bunch of stuff, we use Range to have an asynchronous check-in, where it's actually like you can go back and read through people's check-ins, you can search check-ins, you can attach your GitHub pull request or your Asana tasks, let people what you're know what you're working on that day. That's the asynchronous part, and then being able to see how are people feeling today. We do a traffic light check-in of red, green, or yellow, green being all good and, yellow, sometimes people are a little bit tired. Red is generally big struggles.
With Range we surface information on how's the team doing, what the team is working on, and then all that is fed into the synchronous times. We also have a meeting facilitation tool where you can see the items from people's check-ins that were flagged for a discussion, and so you spend your meeting time just ... it's just higher quality, right? You're not just catching up and doing status updates.
What you all are doing is great because everyone complains about meetings and many teams are still remote. The distributed trend will only continue especially since the pandemic. It reminds me, you started during this time. How long have you been in your role?
A little over a year and a half now. I started in the pandemic. I guess most people would not think that is a good time to start a new job or take a executive role for the first time at a early-stage startup, but it felt like a good time for me. I think a lot of that had to do with the alignment I felt with the team, with the product. Range is all about helping people make work work for them and for their team.
Before the pandemic, I really was not considering going back into full-time employment at a tech company, but it was because I had made up a lot of stories of, oh, I'd have to commute, right? I'm like,"I am not going to commute an hour each way." I've done that, it was really hard on me, and there just weren't that many remote options at that time. I think there was definitely the commute, I had my kids, so I had a lot going on at the time and I didn't really have a lot of energy to go towards navigating team politics, I'll say, as maybe a euphemism for joining a company and everything looks good on the outside and you go and you're like, "Oh, there's a lot of dysfunctional stuff going on here."
I think the opportunity of working at Range with two co-founders that I had worked with before at Medium, that I really trusted and respected, and knowing that the team was small enough that they had hired people personally, and still small enough that I could really play an impactful role on shaping the company and culture. That was really appealing.
And just knowing that I think it's scary to take on a role like this for the first time, especially if you've been out of ... if I had started a role like this right after Medium, I might have felt less like, oh, I'm a bit rusty. I would've just been coming from maybe what made sense as the previous role, something that makes a very clear or progression or a clear narrative, but having been in the leadership development space for three years, I think there was some of what's the manager version of that, what are the gaps I have to fill?
But knowing that I had worked with Dan and Jen before and having a really strong foundation of trust with both of them, I knew I could just show up and they basically know what they're getting, right, because they'd worked with me for so long at Medium. That was really nice, to not have that added stress of starting a new role having that insecurity of proving myself. I was just like, "You know what you're getting, you've worked with me before, and it's almost like you know what you're getting and you have the additional three years of my experience teaching and coaching and selling and engaging with engineering leaders."
That trust bank is so important. Building the trust bank at in an exec role, and your first time in the role, takes effort but you already had the trust built in the founders.
I feel like I took a little bit of a shortcut, but I guess, after the first few years of your career, a lot of people get jobs based on who they had worked with, network connections. Most people are not cold applying to jobs after a certain point.
I think that, as you get further and further into leadership, it happens more often. I don't know if it's a shortcut, I think it's smart, because it's like you started in a pandemic, but you also took away some of the pressures.
Yeah, I de-risked, I think on both ends too, right, I de-risked, they de-risked. When you hire an executive, right ... I've been at places where executives have come in and, a few years later, you're like, "Well, that didn't work out... or like, "Oh, that wasn't a good influence on the team," right? So it was just a good fit in terms of what each of us are getting — what I'm getting out of the role and what the company's getting out of me in that role.
What were the challenges you've navigated being a new leader at a startup, having children, a pandemic?
One really challenging thing is that the pandemic timeline and startup burn rate timelines are the same timeline. Early-stage startups, or startups at all, that are usually not profitable, they don't have the luxury of just saying, "Oh, do whatever you need to do." If the whole company does goes on pause for six months, that's a big deal, right? It's not like, "Oh, we're profitable anyways." It's not like a Netflix or something, where, "Well," shrug, right, "take care of yourselves." I think that one of the challenges I found, and I've heard this from a lot of other managers too, is navigating how to support your team in a way that feels, I guess, aligned with your own integrity of how to be a manager and how to support people and how to make sure the company is moving along and making progress in a way that the company can continue to exist, right? We want to work at this company, I want to work at this company, and so, yeah, there's some balance to find there.
How has it been with having kids?
Yeah. I think I might have blocked some of that from my memory already, but, yeah, last year, or, I guess, last school year, the kids ... well, I think I will preface this by saying, I think we set ourselves up in a situation that made it manageable. My kids' dad and I are divorced. We found another family, or another kid, whose parents are also divorced. Initially, we were just like, "Hey, let's form a little bubble or whatever for three weeks and see how it goes." We ended up with that same pod for a year and a half of four households, so basically four physical households that these three kids could rotate between. They would spend 9 to 5 Monday here, and then 9 to 5 Tuesday at another house, and Wednesday, Thursday ... they would rotate, and so it made the load more manageable and then we hired a babysitter for the mornings.
I think the kids had a really positive experience, both academically and socially, compared to a lot of kids that I feel had a much tougher time, I think. I think what we optimized for, which was kids' experience and their mental health and social health, I think, and the ability for all the parents to be able to keep working, I think all that worked really well. As you can imagine, there were some challenges of our pod being two sets of people who explicitly and legally decided not to be together anymore and their current partners. I joke that it could be a funny sitcom.
It's really smart. It’s seems thoughtful about the challenges and really being reflective about what you needed in order to make your home life and the new job in the middle of a pandemic work well and not cause additional stress.
Yeah, well enough, right? It's all a trade-off. I think it is a challenging thing, I think, for divorced parents, where the pandemic has created a weird ... and I didn't experience much of this, but I've heard about it, of, usually, it's like, "The kids are at your place, you do whatever you want with them. When the kids are at my place, I do whatever I want with them." But, with COVID, there's a lot more, "Well, you can't do this," or, "We need to figure out what we're comfortable with," and a lot of times that's not aligned, right? So it has created a very strange dynamic and put, I think, co-parents in a situation that none of us really expected to be in of just being very involved in the details of each other's lives.
And you’re doing all this while in a VP role, some the same but some quite different from what you’ve done before.
I think one of the big differences about the VP role, at least for me, is how rapidly it can shift.
The first few months, I agreed with the CEO, it made sense for me to ramp up technically and contribute technically, be familiar with the tech stack, and then, quickly, it became clear that that was not where I was going to be most useful, right? It was going to be building some community, building some content, launching Lead Time Chats, my podcast and video series with engineering leaders, that kind of work, and then, pretty quickly, that shifted.
Now I've put Lead Time Chats on pause because I just don't have the bandwidth to do that and hiring, and so now I'm focusing all my efforts on hiring and getting a few engineers in the door. As a VP, you’re maybe more connected to the high-level business needs of what does the company need, so I'm more aware of when what I'm doing is not aligned with that and that my role needs to change.
Especially at an early-stage startup, what you need to do to support the business will change even more rapidly.
Right. I think maybe why I keep returning to these small, early-stage startups is because I like the change. Towards the end of last year, I was doing some more tedious content tasks, and I was doing them, but I was like, "I don't really want to doing these, spending this much time on them," but I also knew, okay, this is just for the next month or two, and then my role's going to change. We're going to hire maybe five engineers total this year. And by the end of the year, that's going to be a totally different role, right?
It's going to be really about empowering the team and supporting the team and making sure that the team processes are set up well, and then maybe I'll go back into content. Who knows? But I think it's just being in touch with what the company needs, having a good relationship with the founders, all that's really important.
I love scaling startups because they're always changing, but they can be chaotic. I love it, but it's not for everybody.
One thing I've realized is that one of my general strengths is doing things really quickly and good enough. It's pretty good, but it's not the best. At larger companies, that may not be a super good strength because it may not be the best. At a larger company or a more stable company, you may want someone to put in the effort to do the best job, but I'm really good at really quickly doing a good enough job.
Maybe that's why I thrive in the startup environment because that's the job, right? You can't be a perfectionist. You can't be too precious about things.
You need to do something, get it out there, it's good enough, and then move on to the next thing, and then maybe come back and, if it's not good enough, then you come back later.
What have you've learned that you’d share with others?
One thing I hear from other people is, "Oh, this is where I want to go, but I think, first, I need to do X, Y, and Z to get there, right? I need to become a manager and then I have to manage more people and then I have to become a director and then I have to do, right, I have to do all these things." I'm like, "Oh, I was never a director," right? I guess just being open to that there are different options to get your needs met. If you look at large companies, it's a bit more structured of what is expected in climbing a ladder, right? You're not going to become a manager of two people and then they're going to put you in a director role at Google, right? That's just not going to happen.
But, at smaller companies, people just wear so many different hats. I guess the advice I'd give to other people is to question or take a look at the assumptions you make about early-stage startups because I think there are many, like, oh, people have to work really long hours or there's always going to be 22-year-old founders that are managing people for the first time, or whatever it is that are your preconceptions of early-stage startups. I think a lot of women, especially, opt out of those because I don't know if they think maybe it's not what they want in terms of their work-life balance.
But, yeah, I'd say explore, talk to a few different ones. Even early-stage startups are vastly different between companies and so, yeah, some may match those preconceptions of you're like, "Oh, I definitely don't want to work here," but there may be some that are what you're looking for and do check all the boxes. Yeah, when I think about the limiting beliefs I had about returning to a full-time in a tech company job, I feel a little bit foolish, not foolish because I think that was pretty realistic pre-pandemic that I would expect to have to commute, but, yeah, just to keep an open mind.
What else to read
Podcast with Sarah Milstein on setting up remote teams for success
What it takes to run better remote meetings
How to hire your first VP of Engineering
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