Pros and Cons of Working Remotely for a Startup

I’ve spent the last decade working at startups that have worked both in-person as well as been remote first. In this article, we’re going to dig into specifically the context of working remotely for smaller startups under a hundred people to help you determine whether or not it’s the right fit for you. Stay until the end for two questions that you can ask yourself to help you figure this out for yourself.

Pros of Working Remotely

Pro 1: Generally intimate team feel.

One of the biggest benefits for working remotely for a startup is that you’re generally going to have a more intimate feel to your team. Because startups are smaller, you will generally get to know people a little bit better than you would if you were working for a publicly-traded company for example.

Something I’ve really enjoyed over the last decade of working for companies less than a hundred people, is that I’ve gotten to know a lot of my coworkers. In many cases, the majority, if not all of my coworkers, and this is something that you simply won’t get at a larger company. If you read my recent article on what it’s like to work remotely in tech, you know that one of the cons I talked about in working remotely is that you don’t get to know your coworkers as much, but that’s even more true when you work for a larger county.

I’ve had friends who have worked at mega-corporations who have shared that over the last year working remotely it’s been really tough for them to get to know their coworkers or to really care because of just how big the team is. There’s simply too many people to have to get to know at a intimate level.

Pro 2: Openness to new ideas.

Startups are generally going to be way more open-minded in terms of trying something new whenever you feel like something has gone stale, or you just want to shake things up a little bit.

For example, in the case of my current company, if we wanted to change a meeting format and just try to test things out, we would immediately be able to implement that in our next sprint or our next bi-weekly meeting. As opposed to in a mega-corporation or a bigger company, you might have to go through a few different iterations of actually pitching your idea before putting it into action in the actual test.

Startups that have generally shifted towards supporting remote-first work have focused a lot on being open to iterating and continuing to iterate and taking this sort of Kaizen continuous improvement approach. This is something that’s really great because it means that your work experience is going to continue to get better and better over time.

Pro 3: Team first mentalities.

The third pro of working remotely for a startup is that I’d say that they tend to have more team first mentalities. Obviously, your mileage may vary here, but what I have personally found is that a lot of startups do care a lot about finding work-life integration or work-life balance for their employees more so than potentially larger companies.

Startups have often led the pack when it comes to answering questions around how to make work sustainable, especially in a remote world. For example, if you were to go through AngelList for some job listings, you notice that a ton of startups are proponents of giving work from home stipends for you to set up your office as well as wellness stipends, and things like to subsidize your at-home gym and other things that just help you have a good, sustainable work-life balance.

Typically, the traditional corporate approach to this is to give you something that feels well a little bit more corporate. They’ll tend to give you something like an at-home tumbler that you can use for your coffee, but it’s nothing that really focuses on improving the employee’s experience.

Now I make a jab here on corporate, but that’s not to say that startups aren’t prone to also going down their swag rabbit holes. It’s just to say that they do focus a lot more time in thinking about how to make work intentional and sustainable for their employees.

Cons of Working Remotely

Con 1: Less organic team bonding.

The first thing that I tell you is that you’re going to generally have less organic team bonding. It’s just much harder to have team-based events when you’re in a remote world, as opposed to an in-person world. Oftentimes, in the pre-global situation world, I would grab dinner with my team members, or we would go for axe throwing or sporting games.

And it would just be a variety of different experiences that we could have together in person. In a remote first company, you simply are not going to get those same experiences. You might have a quarterly or biannual or annual offsite or retreat, but it’s simply not the same as having like a biweekly or monthly team event that you would have in an in-person event.

Con 2: Less office chatter or cross-team interactions.

The only thing that I’d say is a drawback for some people, when it comes to working remotely, is that you’re going to tend to have less office chatter as well as cross-team interactions. Whether you like it or not, there’s always going to be some level of gossip in any company. And so if you’re a fan of having some tea about your coworkers and things like that, you’re not going to have nearly as much of that in a remote world.

Whether you like it or not, there’s always going to be some level of gossip in any company. And so if you’re a fan of having some tea about your coworkers and things like that, you’re not going to have nearly as much of that in a remote world.

But aside from even the gossip side of things, you’re also going to have fewer interactions where if, for example, you’re on the sales team, you could talk to a software engineer and learn more about the work that they’re doing, or just get to know them on a personal level and hang out because the two of you guys buy together.

When you work for a startup where you can go in person and see each other face-to-face, there are tons of opportunities throughout the day in which you guys can just take breaks together or talk about different things that you might not otherwise get to talk to in the remote environment. The reason why I think this is a big drawback, in general, is because these little micro-interactions that you have throughout the day become really big parts of your startup experience.

It’s how you feel connected to your team overall, as well as your company and its mission. And so you have to be a lot more intentional about this when you are looking at things from a remote-first situation.

Con 3: It’s a lot tougher to connect with your company.

In my opinion, there really is something special about working side by side, in the trenches and a small startup in person. I think it’s for that reason that for so many years, Y Combinator has encouraged and promoted their startups going to the Bay Area for the duration of their time in Y Combinator is simply because they get that in-person time, both when they’re working as well as outside of work to get to know each other and really fight for each other as a team.

As with anything, the more time that you naturally spend with one another, the more connected as well as harder that you guys will work for each other. This is something that I really miss when I think back at my last company that I had co-founded in which we would spend hours working in the same 10 x 10 office space before leveling up our offices and continuing to grow the team and just spend time together that we otherwise wouldn’t spend in a remote world.

2 Questions to Figure Out if Working Remotely for a Startup is Right for You:

Now that we covered both sides of working remotely, I want to cover three questions that you might find helpful in asking yourself in determining whether or not remote work is good for you.

  1. What is your number one reason for wanting to work at a startup?

In the case where your answer goes something along the lines of you think that it’d be a little bit less corporate and people would be more fun to hang out with, then you might want to actually explore more in-person opportunities than a remote-first company.

2. Choosing between flexibility and connections, which one is more important to you?

In the case where connections are more important to you, I really would encourage you to have an in-person startup experience first, before you explore the remote first world. The reason why it’s just because you’re going to get to know your coworkers a lot better in this in-person environment.

However, in the case where you really care a lot about your flexibility, you want to have some sort of alternative schedule and things like that, then a remote-first company could be great for you for those purposes. Even today, I still talk to more of my old in-person startup coworkers than I do with my remote-first coworkers, simply because I know them more on a personal level.

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