Employee Engagement & Retention

What It's Really Like to Start a Job Remotely

By Rae Witte

Last updated: Feb 15, 2023

    Table of contents

The remote workforce landscape comes with a lot of benefits..and growing pains - especially when it comes to making big career changes. Here is a tell-all conversation with high-growth startup and corporate employees who started a new job in the most uncertain of circumstances.

During March 2020, 701,000 people lost their jobs in the U.S. as COVID-19 spread across the country and the world. Positions that didn’t qualify as frontline workers quickly pivoted to remote work at a moment’s notice for the first time ever, and in the months that followed statistics show employees gained a better work/life balance, increased productivity in some circumstances and fewer interruptions in their days.

This new workforce landscape doesn’t come without growing pains, and while startups have a tendency to have smaller teams and alternative office setups compared to big corporations, they’ve still been impacted by a completely remote hiring process.

With life and subsequently our workflow vastly different, many people had a lot more time to contemplate whether their jobs were fulfilling enough to stay in for the long haul. While many of the reasons to leave had likely been present before the pandemic, they were amplified by the isolation it brought with it. Whether it was hitting a ceiling in a position, not seeing more opportunities for growth, a desire to relocate, or the shift to remote becoming unmanageable, people wanted a change even in the most uncertain of circumstances.

Leaving the old job

Jordan Brand’s former Global Editorial Lead, Marco Henry, left his job with Nike during the pandemic for startup sneaker community Sole Savy.

“I lived in Portland for three and a half years, and it was not my favorite city. I don't have anything bad to say about it, but you get to a point where you start to say, ‘Hey, I have my dream job, but do I have my dream life outside of work?’”

His exit itself was rather unceremonious without any actual closure. Having already relocated to Los Angeles, it was little more than a few personal emails sent to thank people for their time spent working together and a return-stamped box to send back his laptop.

“To this day, I never saw my desk since I walked out in March 2020,” he says. “There was nobody there. I asked one of my good homies whose desk was next to mine to throw my stuff in a box and send it to me a year after I left the company.”

dusty box

With the vast number of offices being shut down, many companies didn’t even have protocols in place for those not returning after lockdowns.

Logging on...and logging off

Sheeta Verma is on her second new job of the pandemic. The first ended up being a learning experience of what she wished she knew beforehand, which she quickly came to find out.

“The first red flag was when instead of Slack, they were using Discord,” she says, adjusting to instant messaging and digital distribution platform typically leveraged by gamers felt odd to host work conversations. As time went on, she found that there was little onboarding, understanding of company culture, collaboration or investment in her as a new employee.

“I realized a lot of people became founders and got funding in this pandemic, and they don't necessarily have the best attitude, the best way of speaking to people or how to treat employees,” Verma says.

The new position started to feel like it was only about logging on and logging off, with little understanding of the mission, goals, her place in the company or acclimating her to a new team. Quitting the new role was eye opening as well. “They said don't even worry about putting in your two weeks, and they completely took me off all the software and removed my account because they were upset someone was leaving.”


Maintaining the work/life balance

Similarly, Genesis Garcia left her first new job of the pandemic, a small Los Angeles-based startup public relations agency where she was working remotely from Brooklyn, after leaving music label Def Jam. Despite the company emphasizing the importance of mental health as a tentpole of its ethos, things didn’t quite align as her onboarding went on.

“The founder of the company came to New York. Onboarding me in person was nice and I think also it helped to speed up the process. I was able to, kind of, understand all the systems and a grasp of how they work and how to update everything within like a week,” she shared.

But she began to question things when seemingly there wasn’t any real end of the workday in sight, with each day clocking in at around 11 hours. “Obviously, being in a smaller agency you do have to work longer hours, but I did feel a way about the amount of work that I was doing and how little time I was given to complete everything.”

check list

Having opted to join this agency largely in part due to its emphasis on a healthy working environment, as a move away from corporate culture, she found the expectations didn’t align. “I thought that there would be more grace and more patience getting to know systems and being onboarded into all these projects.”

When asking about work/life balance — something one would assume is a priority in a place that emphasizes the importance of mental health — in her first two weeks, Garcia was met with a question about her commitment and ultimately decided to leave and restart her job search.

Heading back to the big music label world, she found she really liked the remote interview process. Aside from the obvious lack in ability to fully connect by seeing someone’s body language, Garcia felt it offered a bit more of an even playing field to interviews.

In addition to the occasional shaky Wi-Fi connection both parties could potentially experience, candidates get a better look into their interviewers' lives, she says. “Rather than feeling like I was stepping into this big office and meeting with the AVP, you're seeing an AVP via Zoom and you’re seeing their dog in the background or hearing their kid screaming or whatever. It just humanizes them more for me.”


Finding the right fit

Having relocated from New York City to Miami, Florida, Julia Perez is also on her second job of the pandemic after her income from digital consulting gigs evaporated by April 2020. In the wellness and beverage startup space, she found a lot of the interviews very similar.

In the end, she ended up with a job working for someone in her network that she reached out to purely for leads. “It seemed like he hired me really fast, which makes sense because we were in the same circle. The other two companies I was talking to were on Zoom with a ton of people.”

The most challenging part for her was the disconnect over video. “It was hard to see if people were bullshitting. I couldn't tell if these people were my tribe or if they were just very charismatic? You can't see their body language.”

At her first new role, Verma realized she didn’t have any insight on the company culture — or as it turned out, lack thereof. Although the interview process was completely digital as well, she found the experience for her second new position very different than the first and much more aligned with her values.

Right off the bat she learned that the founder, who she met with early in the process, is very big on diversity. “Knowing that the founder believes heavily in a company being Black and Brown and having people of color work in it and is empowering us to work in the tech industry was really, really promising,” she says.

“It showed that the company focuses on diversity, inclusion and cares about its people growing.”

She also found out immediately in the interview process that transparency was key to the company, with the founder being open and honest about what they’d done and hadn’t done.“In every meeting, he was very open to asking me if I had any questions, or if there was anything I was uneasy about before joining.”

Knowing what was in the process, what the company was looking to accomplish and what the expectations were of her role gave Verma a lot of confidence in accepting the role.

Getting to know the colleagues

Landing the job is just the beginning though, as we’ve learned from those who are on their second new job of the pandemic. Whether the challenge is like Verma’s in having to learn to use a platform like Discord for interoffice communications, or like Garcia’s where the formerly only-Apple user is having to navigate her company-provided ThinkPad, there will be issues that arise.

Both women found meeting up with their teams in person to be very helpful in initiating a relationship and knowing something about the people they spend so much time with, beyond functionality.

“I met one of my colleagues on a work trip. We had to do a trade show together and it was so nice to get to know her on a personal level and recognize, ‘Wow, this person is a lot like me,’” Perez also shared. “I don't just see her as like the manager of whatever now.”

Henry’s new job at Sole Savy is leveraging a Slack function called Donut, the company’s extension to mimic the office “watercooler,” but he’s found a 20 minute practice at the top of a weekly meeting to be the most helpful in getting to know each other.


“With my team of 10, we start each weekly meeting with a silly prompt like what shoes does everyone regret the most, or what was your most fun pair. It's worth it because some people have funny stories and I think you can truly get to know people through sharing their experiences or, in this case, what they say about a particular shoe.”

The practice has taken the place of the serendipitous occasions his colleagues may have had in an office when someone was wearing an actual pair of sneakers a co-worker may relate to, something so common in a niche sneaker startup.

These practices are valuable as Sole Savy has never had an office and isn’t really planning on having one in the future. “We’re talking about opening small creative spaces in New York and in LA next year and I'm excited about it. I'm really finding myself missing the office because of the creative energy when you're around colleagues.”

While this is definitely a shared feeling across the board, the caveat is that no one said they were looking forward to potentially reverting to a full-time five day in-office work week. “I think my ideal situation would be that I would go into the office, maybe once or twice a week, and have it stay that way forever,” Garcia said.

“There are just so many benefits of working from home, like health wise and time wise, and you lose that when you're commuting,” she says. HR workplace and consulting firm Mercer found that 94% of the 800 employees surveyed said productivity among their teams remained the same or was higher with remote work during the pandemic.

With the perpetual uncertainty approaching our second year in a global pandemic, people want to find parts of their lives that afford them a sense of stability and purpose. Remote work is not leaving the startup space or the workforce any time soon, and those companies finding a way to nurture their talent from a distance will undoubtedly establish a greater opportunity to find success.

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