Welcome back to Taking a Shortcut, a series where we interview our colleagues. The order in which we interview them is random, but that randomization is based on a process in which our Director of Content says everyone’s name into a paper bag, closes the bag, shakes it up, puts the bag in a freezer, takes it out the next day, then interviews whoever’s name echoes back out of the paper bag when he opens it.
If you don’t believe that would actually work, we would like to assure you that it definitely does work and encourage you to try it yourself at home.
These interviews are meant to provide a glimpse into what it's like to work at a remote first company, while also exploring the topics of sailing, football (the soccer one, so the original), and New Jersey. For this week's edition, we spoke with Osei.
Tell us a little about what you do at Shortcut
I am a Backend Engineer. I work on the engagement and retention squad as a Tech Lead. What that means is that in addition to writing backend code, I’m also expected to be a person who can answer questions, or at least find the right person who can answer the questions, for non-engineering people in the squad: Marketing, PMs, anyone. Just generally I need to be able to answer questions more broadly about the things people in the engineering squad are working on.
As a Backend Engineer, I try to work on things that make Shortcut nicer and more engaging to use and bring joy to our customers so they never want to leave. More specifically, I recently worked on the Slack notifications, which I don't know if you use it, but it allows you to stay in Slack, which everyone generally has open all the time, and receive messages that you can quickly respond to.
I do use it and it is very, very helpful. It's so nice to just get notified of a comment and then reply directly in Shortcut via a thread in Slack. This is also a great opportunity for me to link back to our announcement of those new Slack features.
How long have you been at Shortcut and what were you working on before?
I just crossed two years. I think May 7th was two years. Before that I was at a company called Chegg. Are you familiar with Chegg?
I am kinda familiar with Chegg. They do online school stuff, right?
Yes. They're considered EdTech. They're focused on creating resources for students to help them in school. They target college students and I think high school students, but their biggest product is Chegg Study which is like, you can ask questions and have them answered by experts. They have online tutoring. They have stuff like grammar checks. They started off as a textbook rental service, but then they expanded to do other things.
What I did at Chegg was, I actually started off as a mobile engineer, then I expanded to do other things like working on the backend, basically, of the online tutoring service. Then I started getting more involved in things outside of the smaller organization I was part of and I ended up supporting engineers across different squads in the entire company. Before that, I worked at a mobile gaming company.
Going from that mobile gaming company to Chegg was like going from a typical startup that you would imagine working long hours, crazy hours to a more grown-up company. Coming back to a startup at Shortcut, it only interested me because it appeared to be a mature startup run by people who didn't want that crazy all work, all the time life.
Correct me if I'm wrong, but you are always remote, right? Not simply because of the pandemic.
I live in New Jersey. I started off coming to the office on a more regular basis. The first year I came to the office, I don't know, three times a week, maybe more. It was a long time ago. Over the past year, I would definitely come in like once a month, maybe twice a month. Now it's just like everybody is working from home. I think towards the end of last year, I transitioned officially in the system as a remote person working from New Jersey, but I came to the office semi-regularly in the beginning.
What town in New Jersey are you in?
In Montclair. It's like an old town. A lot of New Jersey is. It's like a commuter town, but it has this old small-town vibe. It's a destination. People come to Montclair to go to restaurants and things like that. There are four or five train stations that pass through that are part of the NJ Transit network, so it's pretty easy to get to the city. It's technically a 45-minute commute from the train station here to Penn Station in New York. It ended up being like an hour door-to-door commute. I'd ride my bike to the train station like five minutes away and then take the train into the city.
When I go to New York, I usually fly to Newark, because getting to Manhattan is so much easier from there. Newark has a train that you can get on and then go into Manhattan versus flying to JFK where you’ve essentially landed like two hours away from your destination, so good luck.
The biggest city in the world, it's kind of bizarre.
It really is. When there's not a pandemic and you're not working, what do you like to do?
There’s two things. I like to play soccer, and I would like to play even more soccer. I grew up playing it in Ghana. In Ghana, everybody played soccer. We call it football. So yes, I'd like to play more soccer, period.
I would go to this adult pickup game on Friday nights. After the kids were sleeping, I would go and play soccer with some other dads or whatever and I'd get back home at 11 PM, take a shower and go to bed. It was pretty great. It's a great Friday night activity. It's not what you would expect to be doing on Friday night when you're a 20 something, but here we are.
I learned to sail in college and I've been hooked ever since. Before I came to New Jersey, I lived in the Bay Area and I tried to sail more, but since I’ve had kids, I haven't been able to really commit to that. They're still pretty young. When they get older, I'm definitely going to start doing that again. That's like things I like to do. I also like to make stuff. I like to bake. I like to do some woodworking. I like to work on the house, stuff like that.
How seriously would people take those soccer games? Were those just fun, maybe have a drink right after games? Or were all the dads really going all out to beat the other dads?
It varied. There are some people there that took it really seriously who would almost get into a fight, stuff like that. Most of the people kind of realized that we're just there to get some exercise. It wasn't super serious for me. Some people, as I think with any kind of a competitive sport, some people just take it really seriously all the time. It's the way it is.
Let’s talk about sailing. I've always been interested in sailing, but I don’t even know where to start with it. What makes it so enjoyable?
If you're not familiar with being on the water, it's hard to appreciate how it feels just being out there with nothing powering you but the wind. You're just out in the water and all you hear is the wind and the waves, and you're moving, but you’re never moving all that fast. It's a really relaxing experience, knowing that with the right-sized boat, you can sail anywhere. Wind is unlimited power. It’s just a liberating feeling being out in the water.
When I was in college, I learned sailing by racing. We raced against other schools. It was competitive, but just sailing in general now, it's more relaxing, getting on the water and just passing the time.
Were you racing those other schools on the SF Bay?
In school, I was on the East Coast. I sailed in competitions from Charleston, South Carolina all the way up to Maine. We would sail all the way up and down the east coast. We’d leave campus in our 15-seater van on Friday night, end up at the school and then sail on Saturday and Sunday, and then head back home Sunday night.
What are those competitions like?
We would sail these dinghies, they're small boats ranging from, maybe I think the smallest would be 12-feet long to maybe about 15, 16 feet long. It'll be one, two or three people, and you would have maybe up to 30 boats. A single race would probably be over in about 30 or 40 minutes. There’d be about 10-15 races a day.
You usually sail in a triangular course, and with sailing, you have to race based on the direction of the wind because you're either going upwind or downwind or whatever. Each leg of the triangle is probably about 100 yards,, maybe 200 yards. On some legs, you can't go in a straight line, you have to work with the wind and approach it at angle in order to go where you're trying to go. It's a wholeexperience.
You mentioned that you have kids. How many kids do you have? How old are they?
Two. The older one, a boy, is four, almost five, and the younger one, a girl, is one, almost two in July.
What's it like working from home and also having two kids there at the same time?
It's really hard. Out of all of the people who are under quarantine, the parents of the young kids, I would say, have it the hardest because you can't really do anything with the kids around. You have to make some concessions, like my wife is off on Fridays, but normally I would be in the midst of the chaos, like I'll work in the morning and then she'll work in the afternoon, so we have to switch over. But yes, you can't really do anything, you can't be like, "Okay, yes, go do something and then I'll be over here," because they're all over you, so you have to constantly watch them.
How do you not go insane having to balance your workload with essentially a second job?
Maybe I am insane. This is all just a mask...
But really, it's tough. You just make it happen. Parents make it happen all the time.
You also like to bake, what do you like to bake? Tell me some of your favorites.
I'm new to baking generally. I like to cook, but my most proud thing that I baked is an apple pie. The first time I baked apple pie was this past Thanksgiving.
That's really nice latticework.
I was especially proud of it.
I also like to make pies, but I am terrible at making them look good. My pies are always ugly.
This pie, I found out afterwards that I used twice the amount of butter than is normal. It was really, really good.
What’s something you’ve learned while working at Shortcut or at least had reinforced?
It can work to have a startup environment where there’s not too much bureaucracy, or whatever, which is what people like about startups, and also have really nice people who aren’t just working non-stop. Everybody is super nice. Everybody is really positive and tries to do good work.
It's part of the culture to have a good work-life balance. It's part of the culture to be friendly and to work hard, but also you’re encouraged to have hobbies. You’re encouraged to not be all into your work just by virtue of the fact that people are constantly showcasing things they’re doing that aren’t work. For example, we have this whole Slack channel dedicated to gardening and stuff like that. You don't feel like you have to always be at work or just talk about work stuff when you’re working.
It's a little bit harder now with the quarantine where things are melded irrevocably, but what I learned is that you can have a start-up that has a mature work-life balance. And I'm never leaving Shortcut. Or, if I ever do, it’ll be because I found somewhere exactly like it.