How to Successfully Develop Your Career While Working Remotely

Sep 15, 2021
Develop Your Career While Working Remotely

Last year on the Women in Customer Success Podcast, I had the honour of speaking with Jo Massie, a long-time champion of remote working and managing remote teams. Jo is currently the VP of Customer Success at Slido, a top-rated Q&A and polling platform for live and virtual meetings and events. In this role, she leads around 50 people on the support, success, and customer experience teams—all remotely. One of the best tips I got from Jo during our chat is to get comfortable with the idea of declaring calendar bankruptcy. What exactly does that mean? Read on to find out! It might just be the best thing you can do for yourself this year.


What is the most important technique to help manage your team remotely?

While most employees around the world have been working remotely in the past year, Jo has been working remotely for several years of her customer success career and has a lot of valuable insights about how to manage her team when they aren’t together in person.

With a remote team, you don’t have the same visibility into what people are and you can’t see how people are struggling. Someone’s stress, struggle, or illness might not be as visible as it would be if you were in person, and some people may even make efforts to hide these things. So the most important thing to do for your team is to create an environment where people feel safe and have the opportunity to share what is going on.

Jo recalls when she had someone join her team remotely. This person had an infection that prevented her from moving one of her arms, but she worked every day, and no one even knew about it! In an office setting, team members would see this and encourage her to take time off to take care of herself, but with remote working, Jo did not find out until she proactively reached out.

‘This was a really good lesson for me. You need to create a space where people can say that they’re not feeling well or are struggling with a problem. If you create space and time for your team to talk about these things one-on-one, then you can make sure to get information from your employees and be able to hear their voices.’

Jo Massie


How do you manage your own career when working remotely?

Clearly, it can be easy to get lost in the shuffle when working remotely if you or your team don’t focus on creating touchpoints and transparency like Jo has been working on with her team. I am sure many of us have been struggling over the past year to maintain the same level of visibility in our organizations that we had while working in the office, which can be a stressful challenge for anyone trying to advance their career.

As a long-time veteran of remote working who has worked in several different countries, Jo points out that not only does the lack of face-to-face communication hurt your visibility, but many remote employees who also struggle with time differences between them and others in their organization might have an even harder time finding ways to stay visible. It is important to find which conversations you should be a part of and be much more vocal in sharing your ideas for new projects and how to improve things whenever you can. Sharing the voice of the customer with your organization is also really valuable in the customer success space.

‘I think it’s about tapping into what’s important to your leadership team and making sure that you are seen and recognized as complying with those traits and that you have something to offer. Visibility is really important. Speak up often and don’t be afraid to speak up.’

Jo Massie


How do you manage your schedule while working remotely?

One of the first things I think most of us learn while working remotely is that it is easy for the lines between work and home to start to blend together. It is important to properly manage your time, build a good routine, and work on good time management habits.

When you’re working remotely, it is easy to schedule back-to-back meetings all day long and then just grab dinner and stay on your laptop, working into the night. Building a good, structured routine and implementing boundaries around your work can be a great tool to prevent getting into this habit. Healthy boundaries can help make sure that you shut down every night, take time off, rest and recharge. If you plan on working remotely for the long term, this will be critical to your career success. 

Jo also talks about the idea of declaring calendar bankruptcy, which has been immensely helpful for her to protect her energy and stay focused on her priorities. Calendar bankruptcy is a fun time, about once per year, when Jo plots out her entire week with all the hours she has available and maps out her ideal schedule where she intentionally groups meetings into blocks based on the topic, team, and energy required. 

I’m trying to avoid too much context switching. It makes it a lot easier to focus on things when they logically roll one into another. I also try not to schedule one-on-ones before a big meeting that I’m running because I want to save my energy for where I’ll have the biggest impact. ‘

Jo Massie


Follow Jo and check out the full podcast episode here.