Jenn Leaver Works Remotely

Jenn Leaver Team Photo


Years Remote


Preferred Workspace

Bloomington, IL

Home Base


Fulltime Remote Worker Employee

Jenn Leaver
Interview with

How and why did you start working remotely?

A few years ago, I found myself in an interesting situation; I was a few months pregnant with my second child and had just been laid off. I worked a few contract jobs at home over the next year and a half and loved the flexibility that it provided. When I decided to go back to work full-time, I knew that I would be happiest working remotely. Even though my kids are in daycare and school, working at home gives me the flexibility to be a more active part of their lives. Rather than commuting four hours a day (like I used to!), I’m able to do things like eat breakfast with them, go to their doctor’s appointments, and in general, be there for them in a way that I wasn’t able to before. I found my current position at GitHub through FlexJobs and am grateful every day for the life I have because of it.

What advice would you give someone considering a remote job?

You’ll be most successful as a remote worker if your organization, and especially your direct team, is invested in supporting a remote workforce. That means that async communication is valued, discussions are written down, and people know that decisions can’t always be made in the moment. You’ll also need to make sure that you’re clear in your communication. It’s easy to misinterpret tone in written communication so you’ll need to be highly tuned in to non-verbal cues from your coworkers and clear up any miscommunications before they become issues.

How did you convince your company to let you work remotely?

A little over 60% of the people at GitHub work remotely and the entire Documentation team is distributed. We work in different time zones and have different working hours!

What are the biggest benefits to working remotely?

Working remotely has changed my life. I used to leave for my commute before my daughter was awake and get home in time to eat dinner and put her to bed. Those four extra hours a day give me back precious time that I was missing with my family. It’s the little things that matter so much: bringing my daughter new shoes when she (somehow!) breaks her sandal at school, picking my kids up at the end of the day and still having time to ride bikes outside before dinner, working on the couch next to my son when he’s home sick from daycare, telling my husband to have fun when he leaves on a work trip and not being worried about how I’ll manage to drop off and pick up the kids without him.

What are the greatest challenges to working remotely?

There are days when it’s hard to work at home without any coworkers around. I’m lucky that my husband also works remotely and shares an office with me so I feel a little less alone most days. On days when I’m feeling out-of-touch with my team, I’ll chat a bit more in Slack or have a video conversation with a coworker. Because my team is fully distributed, I don’t experience the fear of missing out that I might otherwise feel. I know that we’re all at home working in our respective offices being interrupted by cats and kids and random visitors!

Do you keep a regular remote work schedule? What is it?

I work roughly the same hours every day. I wake up pretty early to help get the kids ready in the morning and start checking emails and notifications around 7:00 a.m. I tend to make a quick lunch and eat at my desk but sometimes I’ll take a longer break and run errands or do chores around the house (the other day my in-laws stopped by and helped me stake out some landscaping in the backyard!). I stop working around 3:30 p.m. to pick up the kids. Sometimes if there’s other work I want to complete, I’ll jump back on after the kids go to bed around 9:00 p.m. and work for a couple of hours. There are days that I have doctor’s appointments or need to run personal errands for a few hours so on those days I tend to work later at night or catch up on the weekends if needed.

How do you avoid becoming distracted when working remotely?

I have a dedicated office, which cuts down on a lot of distractions. I know that when I go into my office, there’s nothing to do but work! If I’m feeling really distracted, I’ll give in to that. If there’s something on my mind, like an urgent errand I know I need to run or a huge pile of laundry that needs to be folded, I’ll take a break and take care of whatever needs to be done. I’ve found that if I try to work while I’m distracted, I usually end up getting very little actually done. It’s better to just address it head on and then come back to my computer feeling more relaxed.

What is a remote work pain point, and how do you address it?

The biggest pain point with remote work is not having coworkers immediately available when you run into problems. With a distributed workforce, people work in different timezones and have different working hours. I’ve had some really frustrating moments when I just can’t figure out why I’m running into a particular issue and end up being blocked. The solution to that is pretty easy: work on something else. I’ve found that if I let someone know asynchronously that I’m having an issue and then step away from it and work on something else, it will usually get resolved within 24 hours. It’s easy to feel like everything is an emergency that needs an immediate resolution, but the reality is that in my line of work, there are very few situations that can’t wait a day.

What gear can't you work remotely without?

  • External monitor
  • Ergonomic chair

Do you work from a home office? How is it organized?

We’ve converted an extra bedroom into a home office. My husband and I both share it and our desks are against a wall that has a window overlooking our front yard, which is a great vantage point to see Amazon Prime packages getting delivered! We both have extra monitors in addition to our laptops and our backs are fortunate to have ergonomic chairs. We have a dry erase board in our office so that we can keep track of impending work and have some personal artwork hanging. Our office is an extension of our home and our personalities.

How do you stay in touch with virtual teammates?

We use Slack to communicate at GitHub and have a lot of practical channels: ones that are team-specific, or those that focus on affinity groups like women or parents. We also have Slack channels that are just for fun, like the #cat-ops channel, where people post pictures and stories about cats. When you work remotely, you miss out on the random conversations that bond people so it’s important to find other ways to have those moments; sometimes that comes in the form of sharing a picture of your cat sleeping in the sun.

What does your remote company do?

GitHub provides a suite of products that enable people to collaborate effectively with others to develop and maintain software—both in open source projects and in the workplace.

Would you consider returning to a traditional office job, or are you remote for life?

I don’t think I’ll ever work in a traditional office again. I’ve seen firsthand the positive difference that working remotely can make for your personal well-being and the well-being of your family and I don’t want to return to the life I had. I’ve been more engaged and effective in this remote job than I’ve ever been in a traditional office environment.

How has working remotely impacted your career plans?

If anything, working remotely has made me more aware of the vast opportunities that people can have regardless of their geographic location. I had always assumed that I’d need to live near certain tech hubs—cities that were known for their tech communities where I’d have more career opportunities. Now I know that I can live in smaller cities, closer to family and closer to the life I want for my kids, and still have a meaningful career. I have big dreams for my life both personally and professionally, and I’m grateful that one doesn’t have to supersede the other.

How do you stay connected to your professional community virtually?

I’m a part of several Slack teams that are focused on technical writing and content strategy/UX and can be a part of (or just read!) interesting, meaningful conversations between professionals in my field.

What's the best way to develop professional contacts while working remotely?

Finding other professionals in your field via Slack teams, LinkedIn groups, or even meeting people at professional conferences is really helpful. I’ve met more people while working remotely than I ever did while I was working in a traditional office environment. I think that working at home drives me to make more connections outside of my company.

How has your remote job impacted your life outside of work?

A few months ago, we moved to a smaller city. Moving was something my husband and I had never considered because we thought that with our tech jobs, we’d always need to live in a certain area. Since we can both work remotely now, we realized that we could make a massive change and move somewhere that would be better for our family.

How has working remotely impacted your family life?

My husband and I have been able to spend a lot more time together (we work about five feet apart now!) and it’s been wonderful to have quiet mornings with him eating breakfast or doing the dishes together after lunch. I’m able to spend more time with my kids and be the parent I always wanted to be. As parents, we shouldn’t have to choose between our careers and our families, but with the all-too-familiar idea that meaningful work needs to be done in a cubicle during set hours, we’re often forced to focus more on one part of ourselves, to choose what’s more important: family or work. I’m not just a mother, a wife, or a writer; I’m all of these things and by working remotely and blending together these separate identities, I don’t have to lose part of myself to make sure the other parts remain intact.

How do you manage work life integration?

I start working earlier so that I can pick my kids up from school and daycare before 4:00 p.m. and block off time on my work calendar when I have personal obligations. If something comes up that I’d like to do: a day at the zoo with the kids or a short family vacation, I let my team know and put it on my work calendar so that I can set expectations that I’ll be unavailable for a large block of time. I check email throughout the day (I can’t help it!) and sometimes I’ll work at night if there’s something I feel I need to finish up. Even though I have dedicated work time during the day, I know that there are times that I may be doing laundry or running to the grocery store for dinner ingredients and it’s okay for my work time and personal time to overlap and get a bit muddled. Working remotely means your life is more fluid. You don’t have to integrate your work with the rest of your life; you just have to be open to the possibility that you can have it all.