I started working with Highland Management as a contractor, and I want to share my honest experience to help others going into this. While the job seemed flexible at first, I quickly learned that contractors are treated more like employees—but without the benefits or protections. You’re expected to show up and be available as if you’re on payroll, yet you’re paid contractor rates, and unfortunately, those rates are still stuck in pre-COVID times.
I actually worked for them before the pandemic, and when I came back after, nothing had changed in terms of pay. That’s pretty shocking considering the cost of living, gas, and supplies have all gone up. If you choose to work here, track every expense—I noticed my paychecks weren’t always calculated correctly, and I had to stay on top of it constantly.
One of the biggest issues is false promises. You’ll be told there’s work coming, that your schedule will pick up, but often you’re given one or two small cleaning jobs while others (their favorites) get the bulk of the work. There’s clear favoritism, and it shows. They also don’t communicate well, and there’s no real transparency in how they assign jobs or calculate pay.
They go through a lot of workers, and I can see why. The high turnover rate is directly tied to the low pay and lack of consistency. People don’t stick around because this kind of setup just isn’t sustainable for anyone trying to build a life or pay their bills. It might be okay if you’re a stay-at-home mom looking for super part-time work or just a little side cash—but if you’re depending on this income, this is not the job for you.
To be fair, I did enjoy working with Karen—she was always kind—and the office staff were generally nice when I interacted with them. But when I started getting sick and had to miss a few days, things got even worse. My husband had to step in to help, and we noticed our paychecks kept dropping. There was no support, no communication, and no loyalty.
Even some of the customers themselves expressed that Highland doesn’t treat them well. It often feels like the company only cares about money, not the people doing the work or the clients receiving the service.
In the end, I can’t recommend Highland Management unless you’re in a very specific situation where money isn’t a big concern. Otherwise, it’s too unstable, too underpaid, and too frustrating for anyone really trying to make it...
Read moreThese guys are the real deal - everything you want in a property manager and more. Excellent communication, quick responses and assistance, clear expectations, and all around just nice, fun people to work with. I thoroughly enjoy talking to their team on the occasions when I need to.
From the beginning of onboarding, Highline took care to set things up for success, providing realistic expectations for financials and launch time. They are explicit in not taking on more work than they can handle, and by that I mean they provide a very high level of service and they will not sacrifice that just to take on new last minute clients. It's rare to see a commitment to quality and relationships like that and I deeply appreciate it.
They have consistently displayed an eye for "watching the owners money", saving costs where possible for me and finding ways to reduce expense. They also work tirelessly to maximize revenue on rental, balancing cost per night and occupancy, and provide helpful recommendations and guidance for me.
In total, has been a an awesome experience, I wish all service providers were this easy, productive, responsible, and all around joyful to work with. Thanks...
Read moreFamily (actually 6 families) booked a celebration trip through VRBO a year and a half in advance. Paid in full as required by Highline over a year ahead of time. Fast forward, 4 months before our date.... planes, trains, and automobile reservations made... they cancel our reservation claiming a pricing glitch! VRBO offers no recourse. Highline refunds our money (after having it an entire year) then re-posts the rooms without ever offering a compromise! Bad business. Buyers beware, they take your money and penalize you if you cancel but these businesses are allowed to screw you over and get away with it! Will NEVER book through VRBO or Highline EVER AGAIN and will tell our story every chance I get to keep this from happening to...
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