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By Gabrielle Wheaton

A day in the life of property management: Assistant Property Manager – Commercial & Retail Will Fenton

Man walking
Dart Assistant Property Manager – Property Management – Commercial & Retail Will Fenton has worked with the company for coming up on three years. — Photos: Rhian Campbell

Our spotlight this issue focusses on Will Fenton, assistant property manager in the commercial and retail division of our property management team. Considering the timing of his initial application, it seems that Fenton was meant to find his way to Dart.

"This September I will have been here at Dart three years. I love my job," said Fenton. "I had been working at another company as a property manager but changes were on the horizon, so I was looking for something else. I was very lucky because while browsing online one day I saw the ad for the position at Dart. However, the deadline for application was either the day I saw it or the day after, so I really had to scramble to get all my paperwork together. Luckily, I was able to hand-deliver it to Ms. Carrie in the administration department just in time. She enjoys telling the story of how I kept following up to make sure my application would make it through."

Davina Tresidder, Fenton's supervisor, said, "In his two years with us, Will has settled in as a dependable member of the team and his congenial attitude begs favour with our tenants. His easy demeanour brings a unique sense of calm to the chaotic world of property management. I sometimes joke that in a fire he would walk."

CBT: What drew you to this field?

WF: I always had an interest in property management, so I went to university and got myself a degree in property investment & management at the University of the West of England, in Bristol, UK. Then [I] moved back to Cayman and found a job in property management.

 CBT: What is your favourite part of your job?

WF: Working with my team is a big part of it, sitting down with them and figuring out solutions to any issues we may face and generally just learning from and with them. I also like the fact that my job isn’t just being stuck at your desk. You get to go out and interact with your tenants and walk through your properties, which I love because I don’t like being sat in one spot for too long.

CBT: Do you have a set schedule for tasks or is every day different?

WF: I wouldn’t say a set schedule per se, but we do have our set tasks. For example, staying on top of accounts receivable, responding to our tenants' needs, our day-to-day maintenance programmes and then our departmental reports. But the order of these can change from day to day, so you need know when to prioritise.

CBT: What are some examples of the variety of tasks you are presented with as assistant property manager?

WF: Some examples could be any building or facilities issues, like a water leak, an electrical issue or somebody has knocked off your parking barrier, which seems to happen a lot for some reason. Prepping your properties for a hurricane during hurricane season, negotiating contracts for preventative maintenance — the list is endless really.

CBT: Who inspires you?

WF: I would have to say my manager, Davina. When I took this job, I thought I knew a lot and then you quickly realise that you don’t know as much as you think you do. So, Davina, taking me under her wing and working with me closely, teaching me the ins and outs of property management — she really inspired me to continue learning and bettering myself. I couldn’t have asked for a better manager.

 

Timeline of a typical day

Property management is 24/7, really. So when I wake up, I check my work phone to see if any issues have come up overnight.

  • 8-10 a.m.: I will arrive at one of our properties. I log on to my computer and check through my emails and Teams chats to see if there are any emergencies or priority issues to deal with. From there, I will usually take a walk around the property and do an overall check to make sure everything is in working order and running smoothly.
  • 10 a.m.-noon: I will spend this time managing any tenant requests or any unplanned actions that may have come up.
  • Lunch: The timing of lunch can vary, depending on what tasks are on the table.
  • 1-5 p.m.: Continue to work through any tenant requests or emergencies that may have popped up. Then I’ll move on to our administrative work and any reports that need to be done. Towards the end of the day, we may sit down with the team, have a chat and talk about any issues or plan for any tasks or deadlines that we may have.

Once the day is done, I’m back to my second job – looking after my 6-month-old son. And like I mentioned earlier, property management is 24/7, so potentially taking any phone calls after hours for emergencies.

This article was first published in the April/May 2025 print edition of Camana Bay Times.

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