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When Your Office is Outdoors: Julie Singh on full-time travel and remote work

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Julie Singh, Co-founder, TripOutside.

Julie, outdoor adventures are appealing to digital nomads who work and travel. Did you have this in mind when introducing remote work/ work from home policy at your company?

My husband Reet and I founded TripOutside  in 2017 out of a shared enthusiasm for outdoor adventure and travel.  After many frustrating experiences wasting valuable vacation time renting equipment, we created a website that allows others to easily book outdoor gear and adventures online, saving them time and effort and letting them enjoy more of their vacation time.  We travel full-time, gathering information on the best outdoor destinations for our customers by exploring the continent in our motorhome with our cat Juke.

Our office is the outdoors!  It only makes sense that all of our workers are also remote.  It is in our business blood to be nomads!  We want all of our employees, contractors and other workers to also be able to live and work where they want to, hopefully near outdoor adventure!

Having all of your team members work and travel on their own schedule may come at a cost. Are remote workers more or less loyal than in-office employees?

We have had incredible success with remote workers, and we have some awesome individuals working for us in the US and as far away as India and the Philippines.  We definitely assess the people we hire first with small projects, to make sure that we align on work styles, communication and deliverables.  A small project helps us evaluate their quality of work on a smaller scale before we hire them for something larger and more involved.  We have an extremely loyal team, and we love that TripOutside allows them to choose their own workspaces and hours.  I truly believe this helps them to execute their work creatively and produce outstanding deliverables for our company.

Working flexible hours is much appreciated by the millennials. However, having team members working in different time zones may negatively impact productivity.  Are remote workers more or less productive than their peers working 9 to 5?

Based on our experience, a remote worker can be more productive than an employee who is obligated to be at an office for a certain number of hours a day.  Our team (including my husband and I) choose the times, hours and settings that we want to work in, and it allows us to choose when and where we work best without limitations being put on us as to where we need to be and when. 

My husband and I worked in Corporate America for 15 years before we started TripOutside, and we witnessed firsthand the lack of productivity caused by distractions, office politics and unnecessary meetings.  When I would occasionally work from home, I was astounded by the amount of work I got done in less time!  Not only do we save our 45-minute commute twice a day, but we are able to focus so much better in the comfort of our own work environment.  We find that our productivity has really skyrocketed with fewer distractions and being able to choose our own setting.

Open space offices, noise and politics are something no one appreciates. At the same time, having everyone together has benefits on its own.  Is it easier or harder to manage remote teams?

The same components of managing people exist whether you are in an office or working remotely.  As a leader, you need to set clear objectives, communicate consistently, provide guidance and coaching wherever needed, and ensure that deliverables are achieved.  This can be effectively managed by many methods other than in-person.  We never struggle to manage our remote teams because we take advantage of these great tools that exist for communicating.  Here are some of the tools we use:


Concise communication is particularly important for online interactions.  Online communication needs to convey the point quickly and clearly.  At TripOutside, we communicate with our remote teams daily through email, WhatsApp, and other chat messaging apps like Upwork messaging for our contractors.  We use these avenues for short, quick communications like sending documents and links and answering questions.  We find that online chat, in particular, is super helpful for quick questions and messages that don’t require a lot of explanation.  

We also use Google Drive consistently to share documents.  We create shared Google documents that our team can also access, and we use these to create projects, add instructions and review completed work.  

Lastly, we have tried many project management software options to communicate with our developers and keep track of development work.  Trello, Basecamp and Asana are all great project management options, but our favorite is probably Trello.  Their free version has shared dashboards that let you track projects, comments, status, add attachments, and it has a great filtering, labeling and due date system built-in.  It also has email alerts so you know when a project has been updated or comments have been added.


For more extensive training and communication, we utilize video training frequently.  Tools like Snagit allow you to create a video from your computer, with voice and screen “sharing” to show exactly what you are working on and talk them through the training.  The videos are typically large and we save them as shared documents in our Google Drive, so the team can access them as needed.  We use this method for explaining new projects, training our team on processes, and showing them how to use various tools and software.

Phone/Video Calls

When an in-person call or meeting is required, we use Skype, WhatsApp or FB Messenger to have a video call.  There are so many ways to communicate face to face, even when you are miles away from each other.  We use video or phone calls for introductions, weekly status updates, and more complicated brainstorming sessions.  It allows us to spend more time discussing more lengthy subjects and allows us to really connect with our remote teams when we need to.

Lastly a note on Wi-Fi.  Having a strong (4G LTE) and fast (10 mps+) is absolutely critical for remote work.  We do extensive research on our destinations in advance to make sure we will have access to high-speed internet.  Lower Wi-Fi speed or strength means that work just takes longer… and that decreases our productivity significantly. 

You mentioned that your team is not only in the US but also in India and the Philippines. Do remote working arrangements allow you to tap into a diverse talent pool

Absolutely!  There are so many incredible individuals in other parts of the country and across the world. Diverse talents have the knowledge that helps us grow TripOutside in remarkable ways!  If we were limited to hiring employees from just one city, we would definitely miss out on a ton of great talent and would spend a lot more time and money trying to find and recruit the best people.


About the author

Lilia Stoyanov is CEO and angel investor at Transformify. A fintech and digital transformation expert, she is also a professor at Zigurat Business School and expert evaluator Horizon 2020 at the European Commission.

About Transformify

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