Jasmine Tjon Sie Fat – My first months at Headroom

In todays blog, Jasmine Tjon Sie Fat will tell about her journey at Headroom.

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

My first few weeks at Headroom have been exciting and insightful! The onboarding process was smooth, and I’ve been impressed by the team’s supportive and collaborative culture. I’m already getting hands-on experience with inbox and calendar management, and I am learning a lot about very specific tasks.

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

What stood out the most during my onboarding at Headroom was how smooth and well-structured the entire process was. The online training was incredibly comprehensive, providing all the information I needed in a clear and engaging way. It made it easy to get up to speed quickly and feel confident in my role. On top of that, the buddy system worked really well—having a Learning Advocate available at all times for questions made a huge difference. Their support helped reinforce what I was learning and made the experience even more seamless!

As an executive assistant, what do you find most rewarding about supporting CEOs in their day-to-day operations?

The most rewarding part of my role is seeing the genuine appreciation from my members when I take both big and small tasks off their plates. That sense of relief and gratitude makes all the difference.

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

Being able to ask questions within the team and 1:1 sessions to get immediate guidance made it much easier to build confidence in my role. It’s really nice to have the feeling that you can always ask questions and get the help you need.

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

A key lesson I’ve learned in my first months as an EA at Headroom is the value of adaptability and proactive thinking. Each day comes with new challenges, and being able to anticipate needs and stay ahead has been essential.

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

I have experienced my colleagues as very warm and welcoming, showing genuine interest and engagement. They made it very easy to connect and make me feel part of the team. One thing that really helps me feel connected are the digital coffee dates. These casual chats are a great way to stay engaged with everyone, even when working remotely.

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

In a short time, I’ve really developed my communication skills. Working remotely means that what I’m working on isn’t always visible to others, so I’ve learned how important it is to give clear and frequent updates. By doing so, I ensure everyone is aligned and aware of my progress, which helps maintain trust as well.

What has surprised you the most about working at Headroom?

Definitely the warmth of my colleagues and the willingness to help each other out. What also surprised me is how easy and fluid working online can be. The tools and processes make remote collaboration seamless, and I’ve been pleasantly surprised by how well it all works. Despite working remotely, it’s been really rewarding to start establishing a strong, trusting relationship with a member.

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

It’s not easy to take over a member who has already built a strong, long-term relationship with a colleague, especially when you’re new. But when I heard from that colleague that the member was really pleased with my work and had full trust in me, it gave me a huge confidence boost.

What makes supporting entrepreneurs and executives so exciting for you?

It allows me to be part of a fast-paced environment where I can help make a real impact. I love being able to assist in navigating challenges and providing support that allows them to focus on what matters most. The variety of tasks keeps me engaged, and it’s fulfilling to know that my work helps them succeed and grow.

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

My tip would be to prioritize clear and proactive communication. Since you’re working remotely, keeping everyone updated regularly is essential to staying aligned and avoiding misunderstandings. And don’t be afraid to ask questions, there’s plenty of support available, and getting the right information from the start will make all the difference!