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All-Remote Company: What It's Like to Work at Scott's Cheap Flights

It’s not all free flights and company trips to Mexico, but also—yes to all of that

Cheap flight
Photo courtesy of Philip Myrtorp

This article is part of InHerSight's Working During Coronavirus series. As the coronavirus pandemic continues, find helpful advice here on working remotely, job hunting remotely, dealing with anxiety and stress, and staying safe at work if you have to be on-site.

One of the coolest modern side-hustle Cinderella stories is that of Scott’s Cheap Flights, the email-based subscription service that alerts travelers to great deals on airfares all over the world. In 2013, founder Scott Keyes nabbed a nonstop flight from New York City to Milan for $130, and when he got back, everyone he knew wanted him to help them find cheap fares abroad.

Rather than email them individually, Keyes started a MailChimp email list of friends and coworkers. Eighteen months later, his list had grown significantly, and when it finally hit 5,000 subscribers, he decided to turn his hobby into a for-profit startup. In 2016, he took his side hustle full time, having grown his subscriber base from 300 to more than 600,000 in two years.

Of course, an excellent coming-of-age story does not a company culture make, but even as Scott’s has continued to grow and do so quickly, the company has managed to develop a team dynamic that’s arguably just as impressive as Keyes’ startup success—at least according to their female employees.

On InHerSight, Scott’s Cheap Flights scores an almost-perfect 4.8 out of 5.0 stars, earning a neat 5.0 stars for 12 of our 16 rating factors. Women love their wellness initiatives, learning opportunities, paid time off, the ability to telecommute, and flexible work hours, among other metrics.

To find out how exactly the company is earning such positive scores, we reached out to three women working at Scott’s right now: Tasha Champagne, senior customer support advocate; Nicole Rinker, senior customer advocate; and Lindsay Konsko, head of member services. They shared with us their favorite aspects of their company’s culture and benefits.

At InHerSight, we believe making workplaces more inclusive and female-friendly should be a company-led effort. That process starts with gathering feedback from your current employees. Our team can help. Let's talk about how you can take steps in the right direction.

The way Scott’s Cheap Flights hires

Champagne’s journey to Scott’s started with a missed layover in San Francisco. Stranded, she and her husband used Scott’s to book a spontaneous trip to Paris—and then stayed abroad, using the subscription service to visit 30-plus other countries over the course of two years.

When the couple finally returned to the U.S., Champagne, then a Houston-based graphic designer, applied to an open senior customer support advocate position at Scott’s, sharing with them her story. Champagne wasn’t necessarily qualified for the job on paper, but she had been a manager at a restaurant before and had worked with clients online. She says Scott’s embraced her transferable skills.

“Scott’s is really great at looking at a person and fitting them to a role,” Champagne says. “They want to find a culture fit over the exact right person.”

Konsko echoes that sentiment. Hers is an executive-level position that oversees both the customer advocacy branch at Scott’s and the “flight team,” or the people who search for flight deals. Although she has a background in customer support, she says, “Nobody really has a flight background. That’s not really a thing. People are hired based on the qualities they bring to the role. You have to hire on potential.”

As a manager, that meant Konsko faced a learning curve alongside her team, but she says, “Ultimately, at the end of the day, this is a service, so my background suits the role.”

The company values relationships

Scott’s is an all-remote team, with team members throughout the U.S. and the world, making it challenging for coworkers to connect for work, let alone form genuine relationships. However, Champagne, Konsko, and Rinker all say Scott’s emphasizes setting aside time to get to know one another. In addition to using Slack throughout the day and scheduling video meetings, employees are encouraged to book 15-minute casual “doughnut chats” to catch up.

“It’s important that people on my team are viewed as whole humans,” Konsko says, adding that reinforcing the value of personal relationships comes from a management level. “You have to be explicit about it. When you’re connecting with your coworkers, it’s not a waste of time. Work is a social and emotional activity, and it’s important to being productive.”

Rinker, who is based in Surfers Paradise in Australia’s Gold Coast, didn’t meet her hiring managers in person until May 2019—about two years into her role at Scott’s—but she says geography hasn’t been as much of a roadblock as you would think.

To make up for the lack of face time and time zone scheduling difficulties, she’ll often record a video of herself providing feedback instead of sending emails. Scott’s also provides a meet-up allowance so employees traveling to each other’s cities can grab a meal together, and the company hosts annual get-togethers in different countries so everyone can meet in person. Last year’s retreat was in Mexico.

“We’ve been experiencing hyper-growth in the last year,” Rinker says of the company’s recent hires. “But [company culture] is still as true as it was when I first started.”

Scott’s benefits are on-brand

Employees are often wary of companies touting unlimited PTO policies, but Rinker says Scott’s lives the travel-focused values it promotes to its subscribers. A stipulation of the company’s unlimited policy is that employees are required to take at least three weeks off—and naturally, many use that time to rack up sky miles.

“We look at deals every single day, so when a good one comes through, we jump on it,” Rinker says. Some employees even travel together.

Then there are the everyday benefits like flexibility and telecommuting, which, Konsko says, allow people to take care of their families and work where they’re most productive.

But since Scott’s is a flight-searching company that hosts retreats in Mexico, the offbeat perks are, of course, the most envy-inducing.

“Last year, for Christmas, they gave us all a flight,” Champagne says.

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