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Meet Hilary Maddox of Compass

Today we’d like to introduce you to Hilary Maddox.

Thanks for sharing your story with us Hilary. So, let’s start at the beginning and we can move on from there.
I was born in London. We then moved to Paris and Los Angeles before my family put some roots down in Boston. My parents renovated and moved houses 4 times around the Brookline area. So my passion for real estate began early and runs through my blood. I found looking at houses, learning about the renovation, and moving an adventure. My two sisters now live in London and Paris and both have their own successful businesses in residential design.

As with most, it took a while to narrow in on what I wanted to do. I majored in History of Science because I thought I wanted to be a doctor. I ended up landing a job in Investment Banking (biotech focused at least!) because I believed a career in finance was my best immediate route. I wasn’t happy. I worked really hard but never really felt fulfilled. I am a numbers gal but didn’t like being behind a desk all day.

I always kept a constant eye on real estate, especially design and architecture. I could draw out a floorplan of any house I had been in, I could also direct you down almost every street with my eyes closed. When I moved back to Boston, I decided to change careers and make the move to the residential real estate. I couldn’t be happier. I love going into a house – assessing its bones and potential. I love working with buyers – getting to know their style, scouting and searching for the best match. And I love working with sellers – strategizing, packing up and moving on to the adventure ahead. I am challenged every day – a transaction includes numbers, analysis, negotiation, and problem-solving – and it’s different every time and keeps me on my toes!

Has it been a smooth road?
I think the biggest challenge is mastering the work/life balance in a job where you need to be on pretty much 24/7. I began my career in real estate four years ago and it was a quick and steep learning curve. The schedule was very different than a typical ‘9-5’. I found it hard to be available for my clients, hang out with my kids and make time for myself.

I learned quickly I needed to better manage my schedule, set some limits and most importantly ask for help. It’s still not perfect, my days are all so different and I have to be flexible with my moving schedule. But I feel like I am in a great place with a great rhythm now. The buying and selling of a house is a significant transaction. It’s personal and emotional. I love being a part of the process from start to finish with my clients. I commit to working hard to provide an incredible service but want to make sure we have fun in the process. Its a pretty amazing feeling for all when the deal closes and keys are exchanged.

We’d love to hear more about your business.
Compass is exciting! It truly is an innovative residential real estate firm. While most industries have incorporated technology into their business practices, real estate has been slow to adapt. Compass is changing that. The company is building the first modern real estate platform, pairing industry’s top talent with technology to make the search and sell experience smart and seamless.

I’m surrounded by energetic and inspiring agents and staff, all who push me to do better each day. The buying and selling transaction can be complicated and my job is to make it as seamless as possible for my clients. Compass stands out as it provides amazing proprietary tools and support to allow me to give more time to each of my clients. And the staff is looking to make it better each day – my thoughts and feedback are encouraged, I also feel like I have a voice in how some tools are shaped. I’m about to celebrate my one year anniversary with Compass. I am so incredibly happy I made the move.

I specialize in the Brookline and Newton markets. I feel strongly that a client is in the best hands with an agent who knows a specific market and community inside out. On top of being able to recommend local tradesmen and professionals, I can suggest the tastiest burrito for lunch, point out the friendliest dog parks and guide you down the best side-roads to avoid Rt. 9. My kids go to school in Brookline, I coach youth town lacrosse and I have a usual seat at my favorite Pomodoro in Brookline Village. I’m proud to live and work in such a wonderful community.

Is our city a good place to do what you do?
Greater Boston is going through an amazing growth period. For someone starting out in real estate, this is a fantastic market to start out. In some markets, it’s extremely competitive with very low supply, but other areas are growing like a weed. If you love meeting new people, have a knack for numbers, get a thrill when walking into a house, connect with a community, dive into a challenge, enjoy being on the go, real estate could be a great fit!

Contact Info:

Image Credit:

Samara Vise, Joe St. Pierre

Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.


  1. Jim Hall

    January 3, 2018 at 1:05 am

    Great read Hill of Beans…All the best and Hope to see you out in CO some day soon. You look great as do your boys. Happy Healthy New Year…

  2. Tina B

    January 9, 2018 at 5:47 pm

    Loved the article! So proud of you Hil. Big XOXO

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