Remote Work: It’s About More Than Skipping the Commute
The new year always brings a mix of emotions. There’s excitement for fresh starts and the return to routine, along with a touch of bittersweetness that the holidays have come to an end. This week, as I watched my kids walk into their classrooms to begin the spring semester — our third since moving to Miami — I couldn’t help but think back to how much our lives have changed since I joined Help Scout in October 2019.
This was pre-pandemic, when going into an office every day was simply assumed, and remote work in accounting was almost unheard of. I remember the day so vividly because my oldest daughter, who was five at the time, had terrible separation anxiety. I couldn’t take her to school that morning because I was presenting a project as part of my final interview with Help Scout.
She clung to me in tears, panicked, and I pulled away from her, crying myself. I promised her that if I got this job, I would be “home forever.” No more trains. No more missing bedtime. She could count on me being there for drop-offs, pick-ups, and everything in between. She couldn’t believe it — she even made up a little “home forever” song in her excitement.
Luckily, I got the job. I was home forever, and that moment marked the beginning of an entirely different rhythm for our family.
From trade-offs to choices
At the time, I had been commuting from Westchester County into New York City. The commute itself wasn’t bad by city standards, but those 2.5 hours a day added up. With three small children just entering elementary school, every day felt like a trade-off: Should I go to the school assembly, or should I get to the office early? Should I make it to soccer, or should I stay late to finish a project?
Either way, I felt like I wasn’t fully present.
Joining a remote company like Help Scout didn’t erase the push and pull of career and family, but it has completely reframed it. Sometimes I still have to decide between soccer games, meetings, and school events, but now they’re my choices to make, not sacrifices forced by a commute or rigid schedule.
Redefining the workday
One of the most surprising gifts of remote work has been the ability to design my days. For most of the week, I overlap with my team during core hours. That collaboration is essential. But outside of that, I have flexibility:
If my head is clear at 6am, I can dive into deep work while my house is quiet.
If my kids are asleep and I get a burst of energy at 10pm, I can use that time productively.
On Fridays, I can step away for lunch with my husband and make up the time later in the day.
Working outside traditional hours isn’t inefficiency; it’s choosing the moments when I can do my best work. While much of my own story is shaped by parenting, I know that this kind of flexibility benefits people in all kinds of life circumstances — from caregivers to those managing their own health to people who just feel more energetic outside of the 9-5.
Productivity looks different for different people, and that is a strength, not a weakness. Losing the commute and gaining more autonomy has meant lower stress, clearer focus, and more energy for both my work and my family. That is not just good for me, it’s good for the company too.
After all, what matters most is not when or where the work gets done, but the outcomes. The quality of the work, the ownership people bring, and the trust they build with each other are what make teams and businesses truly successful.
That focus on outcomes turned out to matter even more when my family’s life changed in bigger ways.
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Consistency through change
Two years ago, my husband got a new job, and we decided to relocate to Miami. It was one of the hardest decisions we have ever made. We had never lived anywhere other than the New York City area, not even for college, and we both loved it there. But we also wanted to take a leap of faith to show our kids that you don’t have to stay rooted in one place and that it is possible to embrace the opportunities life presents and build something new.
Selling our house, moving through a series of temporary places, and settling into a new city was not easy. In fact, it was one of the toughest transitions of our lives. Still, remote work played a big part in helping us keep some consistency throughout the changes.
Unlike with an in-person role, I was able to stay at Help Scout, keeping our income consistent and eliminating the pressure that would’ve come with a simultaneous job search. The flexibility in my work schedule helped with the logistics of packing, moving, and settling into our new home. Now that the dust has settled, I’ve even been able to find time for workouts with new friends, something that felt impossible when I was commuting.
Remote work has also allowed us to stay connected to our northern roots. Every summer, we return to the Jersey Shore for a season by the beach. That continuity — being able to live in Miami but still give my kids the summers I dreamt of as a child — is one of the gifts in life that I’m most grateful for.
Remote work isn’t always easy
I don’t want to give the impression that remote work is effortless. It’s not. Flexibility is a gift, but it still takes intention — both to do the work and to stay connected to others.
Yes, I am able to be there for school drop-offs and bedtime routines more often. But I’m not an island, and I can’t do it all. For instance, my parents are nearby and they often help with pick-ups and after-school activities when my husband and I can’t get away. Having them as backup has made an enormous difference.
Remote work helps, but it doesn’t erase the very real logistics of raising a family. A strong support system matters, and I still need to be intentional about building structure and sticking to routines. I also have to make sure I don’t isolate myself, which can happen if I’m not careful.
Remote work also comes with subtler challenges that take time to navigate. Without the physical separation of an office, boundaries between work and home can blur, making it harder to fully disconnect. There are fewer organic moments too, like the quick hallway conversations, informal mentoring, and shared context that often happen naturally in person.
None of these challenges outweigh the benefits, but they do require awareness, structure, and thoughtful leadership to address well.
Leading remote teams
As a leader, I have learned that supporting a remote team requires nuance. When you work in-office, things are more straightforward and there are expected norms. However, when working remotely, people need different kinds of support at different times.
Some teammates prefer to work almost entirely asynchronously, thriving in written communication and focused work. Others crave more frequent live connections and want to spend more time “face-to-face.” These preferences can also change with circumstances, roles, and seasons of life.
I’ve found that, personally, I don’t really land in one camp or the other as an employee. I love the opportunities to gather in person: annual company retreats, team offsites, and the occasional coffee or lunch when colleagues are in town. These in-person touchpoints recharge me. At the same time, I love my home office. It’s a space with furniture and décor that inspires me and makes me feel good about spending my days there.
When managing, I’ve found that the key is balancing everyone's preferences in a way that works for the team as a whole. As part of our remote-first culture, Help Scout focuses on transparency and standardized communication. I try to make sure everyone on my team always has the information they need when working on their own.
I also plan for synchronous work opportunities. We have an annual in-person meetup for just the finance team where we can align on goals, plan ahead, and bond as a group. There are also weekly team meetings on Zoom, and I have regular one-on-ones with everyone on my team to connect and understand how I can better support them in their work.
Maintaining the balance between remote independence and intentional connection isn’t easy; you have to work at it. However, I think it’s worth it, as it’s what makes the remote model sustainable.
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Living fully everywhere
This new year, I’m reminded of how grateful I am for that tough choice I made years ago. It was hard to see my daughter distraught that morning, but the choice to present my final project and make the switch to a remote role has made the life my family has built possible.
That one decision gave me not just flexibility, but presence. Over time, that presence has mattered far more than any single schedule, office, or routine ever could. It’s allowed me to be steady through change, to lead with intention, and to show up where it matters most.
The future of work belongs to companies that understand this: Outcomes matter more than hours, being present doesn’t mean being in an office, and well-being is non-negotiable.
Jenny Rush
Jenny Rush is the VP of Finance & Controller at Help Scout, where she leads accounting, finance operations, and governance with a focus on building strong, scalable foundations for the business. Outside of work, Jenny enjoys traveling and spending time with her husband, three kids, and her crazy yellow lab. Connect with her on LinkedIn.
