Last month I had the opportunity to chat with Greg Caplan, founder and CEO of Remote Year (he’s from Chicago BTW!). Their leadership team reached out to everyone in our group to get feedback and talk about how the year was going (pretty cool thing to do).
I used this time to ask a few questions about their success and hiring process – since they’re constantly growing, have only been a company for 2 years, yet seem to have this down (the staff I’ve met are super dedicated and perfect culture fits).
What makes Remote Year work internally – how do you all collaborate as you are located all over the world?
Outside of constant video chats, experiencing things together, he said. Connecting with your team on another level outside of a meeting or work related situation is what seems to drive Remote Year staff – whether that’s going on a hike, side-trip, Karaoke or just coffee.
It’s like we always say – being onsite with your team is when you really bond and get to know each other…and that’s when our teams function best. We should find more opportunities to do this.
I put this to the ultimate test on a 4-day trek to Rainbow Mountain in Peru. A true testament of teamwork and individual mental and physical strength – five of us hiked up to 16,600 ft and camped for 4-days in the middle of no where, next to the Ausangate glaciers and through the night, guided by the stars and milky way, to Rainbow Mountain. Though cold, always out of breath and on little sleep due to barking dogs – each day was an enormous accomplishment and special experience knowing most of the world will never get to see what we saw, together.
What is your hiring process like? How were you able to grow so fast and hire the right people that so perfectly fit the culture/position?
Greg said they use “The Apprentice” model (as much as reference to that show makes me cringe, I get it). They give every potential new-hire a challenge to complete, whether that’s developing a program, group activity, travel for 80 people, budget, etc. – they observe their process and outcome and make decisions based on this exercise, among other things.
We really should do this.
How do you onboard new staff?
Greg said they take shadowing very seriously. They send their new hires to follow those currently in similar positions for days/weeks to literally sit by their side, observe, ask questions and learn in real-time. They also send staff to observe other positions/groups.
I’ve seen this first-hand – for example, their accountant came out to meet us for a week just to see how things go within a program and there is often a newbee staff member around being trained, whom we get to know and eventually see in a future city/country doing their job on their own!
And the #1 question I get…are you profitable yet?
Greg said, “nope.” But, he said that was never his goal. He started this company because he wanted to travel and didn’t want to do it alone – he wanted to create a community of people that could work remotely and travel together…and he wants to continue to offer that (so, you probably won’t see the price increase much).
He told me how he grew up around foreigners – his parents always had friends in town from all over the world or would take in exchange students, expats, travelers…so he grew up hearing stories around the dinner table of other places he had to see.
They do have investors, though – Highland Capital Partners has led a $12 million Series A in the company and other investors include Flybridge Capital Partners (where the deal was led by WeWork Labs co-founder Jesse Middleton) and Airbnb co-founder/CTO Nate Blecharczyk.
Monthly playlist – this one includes a lot of Disney songs…it’s just what seemed to get us through that hike.
OMG, the photos!! This is your most inspirational post to date Alys. To see those sights, I would train to do the hike (but camping for 4 nights with dogs howling…hmmm….) Love the tips on successful hiring and on boarding too, VERY relevant!!