Newlarkers: How we train new members of Olark's support team remotely

Last year, Olark became a remote-first company. We said goodbye to our headquarters in San Francisco and now our 40-person team works from across the US, South America and Europe. We love the benefits of working remotely so much, we’re trying to help others find a remote job too!

One of the benefits of being a remote team is the ability to hire the absolute best person for a given job, regardless of their location. Training Olarkers who are joining the support team is one of my favorite responsibilities in my role as frontline lead. I love getting to know someone and teaching them the ins and outs of support at Olark. But training a remote teammate can also be tricky! Here are a few of the things I do to ensure it goes smoothly.

Document, document, document

The first step to successful remote training is having clear and easy-to-follow documentation for both the training lead and the new hire.

The training lead may not be the same person for every new hire, but all new hires should go through a similar process to ensure that everyone starts off on the right foot. Having clear training documentation that lays out what happens before, during, and after training ensures that regardless of the leader, the process remains the same.

Build a great toolbox

Once you have a clear training plan, it’s important to use the right tools. For our customer support team, that’s a combination of Trello, Slack, Zoom, and Google Docs:

  • Trello — We use Trello for scheduling training events, keeping track of all the docs that need to be read, and listing all the tasks that need to be completed. A ton of people are involved in training a new Olarker, so having a central board that everyone can refer to is vital.




  • Slack — We use Slack for day-to-day conversation and time-sensitive questions from the new hire. The first few days on chat can be nerve-wracking for someone new to the job, and the knowledge that teammates are standing by on Slack to swoop in with quick answers goes a long way toward reducing stress. We also create a personal channel for each new hire, so people can pop in and out of it and say hi during the training process. It puts the onus on existing employees to come say hello, rather than on the new employee to reach out to everyone, which can be kind of intimidating.
  • Zoom — New Olarkers spend a lot of time getting to know the rest of the team in video calls, and for that we use Zoom. We like Zoom because it integrates well with Slack, which makes joining a call easy for everyone on the team. Being able to see someone’s face and read nonverbal cues is hugely important in a remote workplace, especially when you’re new and just beginning to learn about your colleagues and role.
  • Google Docs — Everyone on the support team at Olark needs to be an Olark expert in order to best serve our customers. There’s a lot to learn! To give a new support hire a manageable path to acquiring all that knowledge, we’ve created a support workbook that condenses Olark knowledge into categories that a new Olarker can tackle one at a time. We use Google Docs for this because it makes collaboration super easy, and communicating asynchronously via the workbook makes working across varying time zones much easier.
Download the Olark Live Chat Customer Support Workbook

Support self-care

Starting a new job can be overwhelming. At Olark we strongly believe in approaching work as a marathon, not a sprint, so we make sure to build some #chill time into the training schedule. There’s a ton of new information to absorb and people to get to know, so it’s important to take breaks and set a sustainable pace. I’ve had a couple of new Olarkers ask me what they should do next once they’ve finished a workbook section or a meeting and they’ve still got some time left in the day - my answer is usually “decompress!”

Get everyone involved

While I lead support training at Olark, it’s by no means a one-woman job. Every CS Olarker participates in training a new hire, because we’re a team and it’s vital that anyone joining us gets to know and learn from their coworkers.

After a new hire completes their workbook, we move on to live training using a buddy system. The new hire will do a chat or email shift while on a Zoom call with an established member of the team. This happens over the course of one to two weeks, with the first series of shifts being what we call shadow shifts, with the new Olarker observing their buddy as they work and asking questions. Once they’re comfortable, they switch places and try helping our customers themselves, with their teammate as a mentor. Training ends when a new hire feels comfortable chatting solo. This is something they determine for themselves, and can vary from person to person.

Follow up and keep learning

Once a new hire has had some time to reflect on their training, we sync up for a final check-in so I can seek feedback on their experience. We’re always iterating, and every fresh set of eyes helps us improve the training process.

Finally, learning doesn’t stop when training ends! Everyone at Olark has regular coaching sessions to ensure that they’re continually supported in their new role and able to develop professionally.

Have you ever gone through a remote training process? What was it like for you? We’d love to hear your thoughts!


Check out relevant topics on: Making Business Human, Remote Work

Emily Russell

Read more posts by Emily Russell

Emily is Olark's Frontline Support Lead, AKA Customer Happiness Crusader. When she's not chatting or emailing customers she's enjoying life in Sweden with her best friend -- her dog Luna!