Why I chose Windermere Heritage Bridgeport

When I was getting my license, I looked at three places. On paper, they all had something to offer. In person, it wasn’t close.

The first thing that got me was the vibe of the office, and honestly, the broker owner. Ashleigh and I clicked right away. She has a real, contagious enthusiasm about the business, and it was obvious within minutes that she genuinely cares about her agents, not just their production numbers. Family is something she talks about openly as a value, and I’ve watched that play out since: weekly meetings make space for everyone’s wins and what they actually need, coffee shows up for no particular reason, and she checks in on us as people, not just agents.

The training program was the trade off I went in with eyes open about. It’s new, not the most established out there. But that was part of the appeal. Ashleigh calls me “the guinea pig,” and I mean that as a compliment. I work directly with Shelly, our new agent mentor, one on one, an hour or two a week minimum, and what we cover changes based on what I actually need. One week: SkySlope. The next: touring houses as if I was her agent and she was the buyer. Another week: writing a mock offer and building a full CMA inside Windermere’s systems, so I’d know how to do it for real when it counted. Ashleigh asks for feedback along the way because she wants the program to grow as the office does.

Compare that to the alternatives. One place had a training program with about 50 people in it. I’d have been a number in a room that size. Another had an incredible marketing suite: photography, videography, sign installs, lockbox placement, all handled for you. But I wouldn’t have learned how any of it actually worked. I’d rather learn it now, while I’m small, so that when I eventually pay someone to take it off my plate, I actually know what good work looks like.

That philosophy runs through how I operate today. I do almost everything myself right now: marketing, mileage tracking, accounting. My office administrator helps with open house social content and flyers, and he’s helped me build buyer and seller guides from templates the office already had. But the core of the business is still mine to run.

The practical stuff mattered too: fair commission split, desk fees that didn’t feel outrageous, and a real desk in a real office every day. Other places I looked at were built around remote work, a shared conference room if you wanted to come in, or space you had to pay for by the square foot. I wanted somewhere to go every day, where I could learn from other agents just by being around them.

Longer term, I still want to build my own team someday, my own way. But right now I’m learning a lot just by watching how Ashleigh runs things. She operates across four office locations. I’m taking notes.

📞 (503) 673-3989 📧 palmerbassett@windermere.com 🌐 palmersellspdx.com