Navigating new waters: Elja’s remote onboarding experience

Tell us a little about yourself! You recently started at Headroom! How have your first few weeks been?

I’ve been with Headroom for about four months now. I do remember those first few weeks, a whirlwind, but a fun one! There’s a lot of new stuff coming your way and you want to take it in all at once. Now that I have my own members and have gotten to know them better, I feel more settled in the role.

What made the onboarding at Headroom unique for you, and what stood out the most?

What makes it unique for sure is that it’s fully remote. I can imagine a lot of people wondering if that works. But the training was clear, the onboarding was structured in a way that made sense and most importantly you got the support from all the colleagues. 

Which training or guidance helped you the most in becoming independent quickly?

Honestly? Getting to know all the tools. Every member has their own way of working in different systems, programs, and preferences, so it takes a bit of trial and error to find your way. There were definitely a few “wait… how?” moments, but just as many “aha!” ones too. Next to that, Headroom’s internal Workspace and project management tool really helps creating overview and getting up to speed with all the member info and helps you get up to speed quickly.

What’s a valuable lesson you’ve learned in your first months as an EA at Headroom, and what challenges have you overcome?

Be proactive, but also be patient with yourself. Supporting multiple executives requires a different type of mental flexibility. You’re switching between personalities, workflows, and tools constantly. It takes time to adapt, but that’s also what keeps it interesting.

How do you experience working with your colleagues, and what helps you feel connected in a remote-first environment?

I feel everyone is really open and willing to help each other. I believe that’s the most important thing, whether you’re in an office or not. Buddy calls and coaching check-ins are a very nice way to share thoughts and ideas, get feedback, or just have a casual chat. They really help you feel connected, like you have both a mentor and a team behind you, even from a distance.

Which skill have you developed further in a short time, and how do you apply it in your work?

Letting go is something I’ve been developing, and it’s still very much a work in progress. I’m learning how to balance performing well with accepting that not everything is within my control. It’s about being present and focused during work hours, while also allowing myself to truly disconnect in the evenings. Finding that balance between work and personal life has been one of the most valuable lessons so far.

What has surprised you the most about working at Headroom?

How quickly the days go by. When you are managing different calendars and shifting between tasks for multiple members, time really flies. I was also surprised by how much impact we make. Even founders and CEOs, who often seem to have everything under control, truly benefit from the support we provide. It is rewarding to know that our work plays a meaningful role in their success.

How did it feel to support a member independently for the first time, and can you share a moment you’re proud of?

The first time I supported members independently, things really started to fall into place. You can get to know the member, figure out the best way of working together and settle more into the role.

A fun (and slightly unusual) task I won’t forget: arranging transport contracts for two puppies from the Netherlands to Ibiza. I had never heard of this before and had no idea where to start, but I figured it out and the member was really happy to be reunited with their pups.

What makes supporting entrepreneurs and executives so exciting for you?

When you’re service-minded, there is real satisfaction in helping someone navigate their day more smoothly. It is also inspiring to learn from different companies and the journeys of the entrepreneurs who lead them. You gain valuable insights not only about business but also about people and yourself.

What’s one tip you’d give to someone starting as an EA at Headroom?

Don’t be afraid to ask for help.  It might feel harder in a remote setup, but reaching out makes all the difference. Everyone here wants to support each other, and leaning into that can make your experience more comfortable, especially in the beginning.