Here’s What It’s Like to Work For a Startup

What is it like to work in the pragmatic world of startups? Millennial Jessica Troland shares arduous yet rewarding experiences, along with general takeaways.

*Due to recent mass layoffs, Troland no longer works at Odyssey Magazine. This article was written while Troland was still employed at the company.

On a sunny, moderately warm morning, someone shouts, “Happy Monday!” as they walk through the glass doors of the New York-based, Odyssey Magazine office. Millennials dressed in anything from flannels and khakis to slacks and white button ups pace the office in a hurried frenzy. With coffee mugs in hand, everyone has a full list of tasks to conquer this morning.

For a second, a few heads pop up from their laptop screens with looks of confusion. After quickly shouting, “Happy Monday!” in response, everyone is glued back to their screen — displaying nothing less than 10 tabs per browser.

Welcome to the startup world. Working for a startup presents a new level of challenges and rewards. Whether it be longer hours at the office, little to no daily structure, or the risk of the company failing, one must be willing to be flexible and work hard. Along with the negatives, a startup can also push the employer to develop new skills, discover new passions, and give them a great sense of accomplishment after successfully completing a project.

The Good

Startup companies push all employers to their fullest capacity. Since the company is being built from the ground up with limited funding, employers typically allocate many tasks to few people. For some, they embrace the heightened responsibilities.

“It really shows you what you’re capable of,” said Jessica Troland, 24, the assisting managing editor at the online magazine Odyssey. “I’m pushing myself to grow a little bit faster and handle a little bit more than someone my age typically would.”

Odyssey is an online magazine that lets the millennial generation voice their opinions and thoughts. With 30 million unique viewers a month, the site democratizes content and brings a local voice back to smaller communities. Odyssey then places this local content on a platform to share with broader audiences.

At the 7-year-old startup, Troland, manages an average of 200 content creators and 20 communities. She is also the creator and manager of the training program — a project she was assigned unexpectedly. With no prior background on how to train incoming employers, Troland had to build the program from the ground up. “I have been put in those situations multiple times where I have to just take it and I have to just make it work. Doing that while you’re young teaches you how to manage people, work with people, and get things done,” she says.

Troland started working at Odyssey around five months ago. At the company, she says she has no real job description. “At a startup, I would say your job title is a little more non-traditional than it normally is. You’re wearing a lot of hats, you’re doing a lot of things,” said Troland.

Wearing so many “hats” has also allowed Troland to curate new passions. “You do a lot of building honestly. And I didn’t know that I loved that but I do,” she says. “When you finish everything and you step back and take a look you say ‘wow I really did that and I did good.’”

The Bad

Lack of structure within startups is an issue employees share across the board. Troland also dislikes the lack of structure at her job. As previously mentioned, Troland has no official job description nor set schedule from day to day. “I can get thrown in one direction and the next day have to go into a complete different one.”

No daily structure also causes blurred lines between when Troland is on and off the clock. “Hours are much longer. You do not work a typical nine to five, you end up working from nine to six or seven,” she says. There have been nights where I’ve worked until 9 p.m because I had things to do and I needed to get them done because literally no one else was going to do it.”

“You’re essentially building a company. And I don’t think a lot of people know what that means because we’re so used to seeing companies already built,” said Troland. “But when it comes to building a startup, you don’t really see all that goes into building something like that. So for me it was kind of a shocker honestly.”

Critics also mention the risk of startup companies failing or offering scanty salaries. According to research from the Statistic Brain, 25 percent of startups don’t survive past the first year while 55 percent fail by year five.

To Troland, the possibility of failure is not much different compared to any other company. “Big companies do layoffs all the time. You see it a little more up close and personal [with a startup] than at a big company, but I think as long as you’re doing your job and the companies working well then that’s something you don’t worry about too much.”

Financially, Troland says she feels no strain. “Personally, I’ve had good experiences with finances. Where I am now, I actually find they pay more than the traditional role. They are looking to have a competitive aspect when they’re hiring people so they offer a competitive salary, which is nice.”

Although these companies offer competitive pay, Troland says insurance benefits are often slim to none at a startup. According to the Go Co Blog, only 28 percent of businesses with fewer than 10 employees offer health insurance.

Startup employers often emphasize the amount of hard work that goes into the company. Working for a young company is not for the faint of heart. All workers must be willing to put their best effort forward.


Flexibility is also key working at a startup. Anyone who wants to work for one must be willing to change directions at any point in time. “I make my own schedule” said Odyssey employee Jessica Troland. “You kind of flex with the company […] I know what I have to get done. I set up shop, figure out the time I need to do it, and check off all the boxes by the end of the week.”

In general, startups offer the employee the chance to make a more prominent impact in their company. They learn more, fail more, and are forced to contribute every possible talent they have. Startups offer endless creative freedom unlike established companies with more rigid job descriptions. Considering all the opportunities for growth at a startup company, employees should be willing to get whatever they can out of the experience.

Article written by Amber Oates, Content Strategist at The Tech Connection

Amber is a journalist passionate about all things fashion, beauty, and hair. The Boston resident never passes on a chance to travel anywhere and everywhere. Follow her on Twitter at @amberboates1.

The Tech Connection is a recruitment platform that supports the professional development of untapped technical talent. We offer individualized career planning and job placement to candidates. We believe that introspective leadership coupled with proper planning is the key to career success. We strive to deliver the best talent to high performing and innovative teams.

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