Hello! What's your name, your company name and your role there?

Jake Peters, HelpDocs, CEO
Can you give a brief overview of the company background and what you guys do?

We make self-serve customer support software that helps our customers help their customers, freeing up time for the important support tickets and increasing end-user happiness along the way. When we launched HelpDocs in June 2016 we wanted to build a simple knowledge base platform. Now we serve millions of article every month, power docs for Fortune 100 companies, charities, and fledgling startups. We help some of the greatest teams free up time to do their best work for their amazing customers.
What percentage of your company works remotely and have you always been remote-friendly? If not, what prompted the change?

100%, always fully remote
What do you see as the biggest advantages of working remotely?

We get to work where we're most comfortable, which means higher quality and less mental anguish. Plus no commute.
What are the biggest challenges you've faced and the obstacles you've overcome? If you had to start over, what would you do differently?

Communication's been the biggest challenge so far. It's tough to get the right balance of leaving everyone to do their jobs, and making sure there's enough time to chat and have those "water cooler moments". Hiring's also been tough, since at the start you're not really sure what you're looking for in a remote employee. It's more difficult to assess how someone will perform in a remote environment, especially if it's their first remote gig. If I had to start over I'd probably hire sooner. We left it nearly 2 years before our first full-time employee.
What do you look for in a remote employee and how do you hire for good company fit?

The most important two things I'm looking for are culture fit and communication. Generally we do interviews on Slack, rather than by phone or video call. That way we're getting an idea of how candidates handle waiting for replies, how fast they type/think, what they're like to chat with in the context they'll be working. It's pretty revealing.
What elements make up a successful remote team? What’s the trickiest aspect to leading and managing a remote team?

It's all about people. There's so many phenomenal people out there, but not all of them are great at working remotely. To be successful you need people that're able to work in relative isolation, since the bulk of their time won't be spent in an office-like environment. They also need to be able to communicate really well, asynchronously, since they'll often be dealing with timezones and waiting around for replies.
How do you nurture your culture and the personal relationships within the company?

We have an active #random channel on Slack, where we post things that're happening in our lives outside of work. Plus an excellent set of custom emoji, from famous figures to a bottle of ketchup.
What advise would you give to a team just starting out as a remote company or a team transitioning to remote work?

Make sure it's what you actually want to do. If you're not cut out for remote working yourself, you're not going to get very far running a remote team. While sitting at home in your underwear writing code sounds fun, it can be lonely.
Company Mission
We help our customers help their customers, free up time for the important support tickets, and increase end-user happiness along the way.