What I Learned My First Month Working at a Remote Startup


I’ve never been one to take many risks. In fact, I will go out of my way to avoid risky situations. I find comfort in the known and appreciate a predictable routine. I value organization (hello spreadsheets and to-do lists!), structure and clear direction. This is why I shocked the hell out of a lot of people when I decided to trade in my job at a well-established corporate office for a new position with a remote startup. (…Six months after having my first born.)

Now, one month later, I’m sitting in my home office with my cat on my lap, rocking yoga pants and a hoodie with my dryer running in the background. Transitioning from working in a corporate environment to a remote startup doesn’t happen overnight, and I’m still figuring it out. However, I think it’s a good time to reflect and share what I’ve learned over the last month. First, I’d like to address the three questions everyone asks me about working for a remote startup.

3 Questions Everyone Has About Working for a Remote Startup

  1. “Oh, you work from home now? That must be so nice to be home with your son all day.”
    This one always blows my mind. Maybe it’s because my son spent the first three months of his life crying, or maybe it’s because working (wherever it may be) is my adult time. Whatever the reason, even though I work from home, my son still goes to daycare. For me, this makes me a better employee and a better mom.
  2. “How do you actually get work done when you’re at home?”
    You don’t need to be in an office to be productive – you just need to be in the mindset. Working from home does blur the lines between my professional and personal life. While I stay pretty focused on my work from the normal 9-5 hours, working from home does give me the flexibility to do personal tasks during the day, if needed. Retrospectively, it’s not unusual for me to work on small projects after my son goes to bed. It also doesn’t hurt that I love what I do, and our company allows for a flexible schedule.
  3. “Doesn’t it make you nervous working for a startup? What if it doesn’t work out?”
    Legit question for someone as risk-adverse as myself. When I made the decision to join VIP Crowd, I went all in with the rest of the team. You can’t halfheartedly join a startup, and be working on a plan b in case it doesn’t work out. If you don’t believe in what you’re doing, how do you expect others to buy in? Jump in, get your hands dirty and start proving the value to others.

3 More Things You Need to Know About Working for a Remote Startup

  1. Adaptability is key.
    In the early days of a startup, you have to be willing to put everything you have into what you’re working on… and be willing to completely scrap it and change directions at any time. Being able to “go with the flow” is absolutely essential, and you just need to enjoy the journey.
  2. You get lonely sometimes.
    I’m a total introvert and prefer to work quietly on my own, but when you’re doing it all the time it can get lonely. At least once a week, I venture off to a coffee shop or restaurant just be around people for a while.
  3. Communication and collaboration are more important than ever.
    Things can change quickly in a startup, so it is crucial to make sure everyone is on the same page. Working remotely adds to the challenge. Weekly calls and occasional on-site get togethers go a long way. Also, using tools like Slack and Trello helps you keep an open line of communication with your co-workers on a daily basis.

Working for a remote startup may not be for everyone, but so far it’s working out pretty well for me. I’m happier, more engaged and glad I took the calculated risk to step out of my comfort zone and join the VIP Crowd team.


  1. Jessica Staszak Abitz

    Great insights about working from home. I can relate. Thanks for sharing your perspective. Congrats on the new gig; happy to hear you are enjoying it!

  2. Sara Kerwin

    Thank you, Jessica!

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