Hi there, yes, you read that right! There are fourteen (at least) companies that will PAY YOU TO TAKE A VACATION! Per Flexjobs, a premium online job service, more and more companies are beginning to realize how vital taking a vacation is! So, they’ve done their research and listed fourteen companies that are HELPING their employees do just that!

Flexjobs logo
Flexjobs logo

These companies all offer remote-work options, and help pay for their employees’ vacations! They WANT you to enjoy your job AND your life! Can you say that about your current job?! I can’t.. which begs the question, when am I going to be applying somewhere else!? LOL! Soon!  

The list:

AFAR Media

 AFAR Media is a travel media brand that seeks to inspire global travel. The company has a magazine, along with a website that features travel guides and articles. According to a blog post posted by the company, full-time employees receive 30 days of vacation time and a $2,000 stipend to encourage them to travel to new places.

Airbnb

 Airbnb was established in 2008 as an online hospitality marketplace for hosts and travelers to connect and features listings for homes, rooms for rent, villas, boutique hotels, and more. It has served thousands of people through its 2 million worldwide listings. Employees receive annual travel and expenses credits.

BambooHR

 BambooHR is an HR software solutions company that seeks to help companies move beyond spreadsheets. It offers software to help with applicant tracking, employee onboarding, time-off management, employee database, and more. Located in Lindon, Utah, the company has hired for part-time and remote jobs in the area. BambooHR offers employees what they call “paid paid vacation“—$2,000 each year to travel as you please.

Basecamp

 Basecamp, founded in 1999, is the creator of a popular project management tool of the same name. The distributed company has 50 employees working across 32 cities. According to Business Insider, employees who have worked with the company for one year or more get to choose from 16 different paid vacation packages each year. These trips are valued at $4,000-$5,000 each.

Bonanza

 Since its establishment in 2008, this online marketplace has been on a mission to empower entrepreneurs in building “a sustainable business based on repeat customers.” During “Freedom February,” the eCommerce company physically moves its office to a tropical location for the month and gives employees a bonus and extra personal days.

I swear, I’m salivating at the THOUGHT of getting paid to vacation! What about you?! Shall we continue?!
FlexJobs membership info
FlexJobs membership info

Evernote

 Evernote is an all-encompassing app that allows users to capture, organize, and share notes in one place. Links, tables, audio messages, and more can be included in each note. Evernote is located in Mountain View, California, and has offered freelance jobs in the past. The company offers employees unlimited vacation days and a $1,000 yearly vacation stipend.

Expedia

 As a well-known travel booking site, Expedia has served clients in more than 60 countries worldwide. Users of the site can book flights, hotels, rental cars, cruises, and even activities. As an employer, Expedia hires for freelance and telecommute positions. Employees of the company receive travel reimbursement, ranges depending on tenure. They also receive discounts on retail and travel packages purchased through the site.

FullContact

 Another company that pays for your vacation, FullContact is a platform that helps businesses and individuals develop and maintain business relationships. It helps in the areas of identity resolution, contact management, profile enrichment, audience insights and development, fraud prevention, and customer care. FullContact provides $7,500 per year for employees to travel—and it’s required that they don’t work while on vacation!

Motley Fool

 Motley Fool seeks to “make the world smarter, happier, and richer” through its business and investing advice. In addition to offering unlimited vacation time, the company also has a “Fool’s Errand” program where one employee’s name is drawn from a hat every month and awarded “a decent chunk of money” towards a two-week vacation. The lucky winner has to take the trip before the next monthly meeting and is asked for no contact during their travels to ensure the ultimate in relaxation.

I was thinking that Motley Fool is a band…am I the only one?! ((BTW, it’s NOT a band – but Motley Crue is!)) Let’s keep reviewing!

Moz

 Moz is a software as a service (SaaS) company that develops software for inbound marketing, hosts vibrant communities of online marketers, and provides APIs for link data and social influence. The rundown of what Moz employees receive for vacation is: 21 days paid time off per year, seven days of sick leave, 10 paid holidays, and $3,000 per year vacation expense reimbursement.

Travelzoo

 Travelzoo is a commerce site in business since 1998. It publishes travel deals from over 2,000 entertainment, travel, and local companies to an audience of 28 million members across the world. It also offers exclusive deals and rates to members who join the site. According to Glassdoor, employees of Travelzoo are offered a “$1,500 stipend and three extra days of PTO to ‘book a hotel stay, vacation package, cruise, or flight offer that we negotiate on behalf of our 28 million members worldwide,’ states Michael Stitt, President of Travelzoo North America.”

TripAdvisor

 As the world’s largest travel site, TripAdvisor serves more than 350 million users monthly. Users can book flights, hotels, vacation rentals, restaurants, and more. The site boasts a large database of user reviews to help customers make the right travel choices for their needs. As a company, TripAdvisor offers a travel reimbursement of $250 or more, depending on how long an employee has worked at the company. It also offers discounts on packages offered through the website.

I never considered even applying for a place like TripAdvisor!! Why IS that!?

United Airlines

 Founded in 1926, United Airlines now hosts 4,500 flights every day to more than 335 airports on five continents. As one of the largest airlines in the world, United Airlines seeks to be an inclusive employer and is named one of the “World’s Most Admired Companies” by Fortune magazine. The company offers discounted airline tickets and unlimited standby travel on any United flight to employees.

Yesware

 Founded in 2010, Yesware is a technology company that provides email services for salespeople. Core features of the company’s product include campaigns, email tracking, a LinkedIn sales navigator, reporting and analytics, Salesforce integration, and templates. The Boston-based tech company offers employees a large travel stipend to fund a dream trip when they celebrate their five-year anniversary at the company.

Do you know of any other companies offering these kinds of incentives to employees? Drop me a comment; I’d love to know!

I found out about this AMAZING site, FlexJobs, by Kathy Gardner, who admittedly reached out to me awhile ago! Since this is a crazy year, it took awhile to get this out here! I asked her a few follow-up questions, which she was happy to help me with, and those are here: 

Me: Sara Sutton began the FlexJob site in 2007 – what was her inspiration for this?

Kathy: Sara Sutton has long been passionate about helping people find jobs and she started her career in 1995 when she co-founded JobDirect, the first online entry-level job service (sold to Korn|Ferry International in 2000). Sara founded FlexJobs in 2007 while she was pregnant with her first son in response to her frustrating search for flexible work that would fit with her career and her family. Her quest for work-life balance helped her form the idea for FlexJobs. She knew these types of jobs existed – professional-level, career-oriented jobs that offered flexible work options like remote work and flexible scheduling, but they were difficult to find amid the many scammy listings out there. She wanted to create a quality service to help professionals find the work flexibility they needed and wanted for their lives. 

I can’t agree with THAT more – the SCAMS!

Me: What kind of growth is FlexJobs looking to see in the next 5 or 10 years? What direction is the company moving towards?

Kathy: The last 10 to 15 years have been a time of steady, regular growth for remote and flexible work options and we expect to see that continue into the future. Even during the last recession, remote job opportunities grew each year even as the rest of the job market was shrinking. Now, as a result of the COVID-19 crisis, we’ve seen a dramatic shift towards remote work across the board that may have profound effects on the remote job market for years to come. 

Me: Does FlexJobs or Ms. Sutton think that due to the COVID pandemic, things will be changed long-term in the future concerning most business organizations?

Kathy: Absolutely. Many companies have already decided to extend their remote work options through 2020 and beyond, with companies like Facebook and Twitter making the decision to shift a huge portion of their workforces to completely remote work in the coming years. Outside of a crisis situation like this, where remote work has proven its ability to maintain business continuity and allow people to be productive and effective during the most challenging times, remote work offers very real and long-lasting benefits for companies (cost savings, productivity increases, a more diverse talent pool, better employee retention, lessening environmental impact) and workers (savings of time and money, lowered stress, increased job opportunities). 

Sara Sutton, CEO and Founder of FlexJobs!
Sara Sutton, CEO and Founder of FlexJobs!
My final thoughts on FlexJobs:

Wow, just wow! I’m going to be looking, starting pretty immediately on their site for work that would suit my busy, crazy, always exploring life! You should, too, if you’re reading this! I’d love a comment, or share!

Kathy, thank you SO MUCH for all of the information, I appreciate it!! This is excellent, and I don’t see FlexJobs going anywhere anytime soon! They’re too useful!  

You can go out and follow FlexJobs on all of their social media handles for the most up-to-date info! (I’d love to know how it goes!) FB: @flexjobs ; LinkedIn: The FlexJobs Group ; Twitter: @FlexJobs ; YouTube: flexjobs ; Pinterest: flexjobs ; IG: @flexjobs.

Speaking of wanting to work from home, in case you weren’t aware, I’ve recently started my own #WIP (or work in progress, for you non-Twitter users!), which you can check out here if you’re so inclined 🙂 I’m thinking I’ll TRY to turn it into a mystery/thriller kind of novel!

Love ya,

Kelly Ann

Relevant hashtags if you’d like to share: which I’d appreciate! #flex #flexjobs #workfromhome #flexible #careers #experience #jobs #job #parents #families #search #jobsearch #service #platform #trusted #flexiblework#

Thanks for the share! Follow if you'd like!

2 Replies to “14 Companies That Will Pay You To Take A Vacation per FlexJobs.com”

  1. Many of these companies are travel related. That field is hurting for sure. I wonder if that is affecting any of these benefits they offer and/or the number of jobs they are offering. It sounds great, but that would be my only worry.

    1. That’s totally fair! The nice thing about FlexJobs is that these are just the ones they’ve called out that pay for their employees vacays!! I was playing around on their website while writing this article and there are a TON of companies hiring remote workers!! It’s a fantastic opportunity when you want to work from home! 🙂

Come on, give me some feedback! :) :) :) THANK YOU!

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