Hello!
I’m Caitlin and I’m the Onboarding & Training Specialist here at Resident.
My First Weeks: From Onboardee to Onboarding Specialist
It’s hard to believe it’s already been a year since I joined the team! When I think back to my first few weeks, I remember how surreal it felt to be going through the onboarding process myself, knowing that I’d soon be responsible for guiding others through it. At the time block management was completely new to me and like anyone starting something unfamiliar I had the usual mix of excitement and nerves. A year on, I’ve now led hundreds of onboarding and paid training sessions and it’s been incredibly rewarding to support so many clients on their journey with Resident.
Embracing Resident’s Remote-First Culture
Before joining I’d worked remotely for almost three years so the adjustment into Resident’s remote-first setup felt natural. What made it stand out though was the culture. From day one it was clear that this wasn’t just another company. It’s a small team where people genuinely care about what they do and support each other at every turn.
Connecting Beyond the Screen
Meeting the team in person over Christmas last year was a real highlight. Working remotely means almost all of our interactions happen on screen but meeting face to face only reinforced the positive dynamic that Resident has. It was great to spend time together and feel part of something even more collaborative.
Growing Skills and Taking on New Projects
Something I’ve really valued over the past year is the opportunity to grow in so many ways. My confidence in delivering sessions has developed massively and I’ve had the chance to explore areas I’d never worked in before – from creating training videos to contributing to wider projects like the Nylas integration and the launch of Auto Reconciliation. Each project has given me the chance to learn something new and feel even more embedded in the work we do as a team.
Building Confidence and Expertise
One thing that stands out to me now is how much my understanding of the system has evolved. A year ago I was just beginning to piece it all together and now I’m in a position where I can confidently guide others, troubleshoot issues and offer training that really helps people get the most out of Resident. That’s probably what I’m most proud of – the progress, the learning and the impact I’ve been able to make in just a year.
The Value of Mentorship
Working closely with my manager Craig has also played a big part in that journey. His support and mentorship has been so valuable, especially during those early months, and having someone who understands the role inside out has made all the difference.
Looking Back—and Ahead
Looking back, this year has gone quickly but it’s been full of meaningful experiences. I’ve learned a huge amount, grown professionally and worked with some brilliant clients and colleagues along the way. I’m really excited to see what the next year brings and to keep building on everything we’ve achieved so far.
Thanks to everyone who’s been a part of the journey.
