Jen Dillard | Turning Real Estate Dreams Into Reality - GOSS
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Jen Dillard | Turning Real Estate Dreams Into Reality

Meet Jen Dillard, business woman and real estate investor who in just four years created a team that this year alone surpassed over 70 million dollars in sales. Jen has been in the real estate industry for over a decade, and has amassed a huge network of professionals and experience that sets her apart as one of the top producers in her region. Her biggest asset is the mentorship she provides to other agents, which has also made her team grow and expand naturally. She is a mother of two, and a wife to a loving and supportive husband. More on her passionate story and on building a successful brand below.


Tell us a little about yourself and your story?

I am a city girl gone country! I was born in Los Angeles and grew up in the Seattle area. My husband is from Hood River, Oregon, which is where we live now. We really loved visiting family here, so we decided to make the move and raise our kids in the Columbia River Gorge. Hood River is a small town about 1 hour East of Portland, Oregon. It has earned a reputation as one of the world’s premier wind-sport destinations and is known for its proximity to downhill skiing, world-class whitewater, view-filled hikes, and incredible mountain-biking trails. It’s really an amazing place to raise kids because there is so much room to roam and so many things to do.

I started my career in the real estate industry in 2007.  In 2015, after I had my second child I realized that I had really missed the feeling that Real Estate gave me. The joys of helping someone find their dream home, being there to guide someone through the process after a major life event such as divorce or death of a family member, and the flexibility that Real Estate gave me to be there for my own family. I was able to do what I love and still be a great mama and wife.  I’m a very driven person and I have an entrepreneurial spirit with a tremendous amount of love for business. Being away from it took a toll on me, pushing me to get back into the game. I love being a mom, but I know I’m a much better mom when I’m also doing the things that fill my cup. I think there is this stigma around working moms, that you must choose between your kids or yourself, which couldn’t be further form the truth. I work hard and I have boundaries when it comes to my family.

I also have my incredible team to thank, they allow me to have a balanced work/family life. I couldn’t do what I do without them. 


Tell us about your journey from 2015 to today?

In 2015, I started working for a boutique brokerage firm in Seattle. When we decided to move to Hood River in 2017, I was lucky to have the support of my brokerage and they gave me the opportunity to open a Hood River branch.  The brokerage merged with a national brokerage after 1 year of opening and I found myself  needing to find a new firm to join.  After searching for the perfect fit, I found Hasson Company Realtors with whom I’m currently affiliated with. Hasson allows me to be creative and use my passion for growing a business, while still being under their umbrella and benefitting from all they have to offer. I specialize in residential and commercial real estate. 

I started my team three years ago when I hired my first agent who is still a big part of my team. I met him at a coffee shop, where he was working and loved his personality so much. I struck up conversation one day by asking him what he was passionate about in life and one thing led to the next. He told me that he had a family and just moved back to Hood River where he was born and raised. He said that he loved sales and I told him if he ever wanted to consider doing real estate to call me.  Not too long after that conversation, he called! He studied and got his real estate license and he has been with me ever since. He is crushing it in Real Estate and just bought his first house…his story is one that inspires me to continue to mentor agents that have a passion for the industry.

After hiring my first agent, things continued to grow organically. Our team has always been about quality over quantity. As Mike Hasson (founder of Hasson Company) once said, “We are not about being the biggest, but the best.”

I now have a team of nine agents along with three support staff. Last year we did 21 million dollars in sales and this year we are going to top over 75 million! This team is just getting started! 


What do you think helped in your jump from 21 to 75 million in sales?

The Real Estate market in 2021 was more active than I have ever seen it.  Our area is one of the top small towns to live in according to several sources. It has been featured in many magazines as a destination and now that people are able to work remotely more than ever before, they are choosing to live where they play!  It’s the new lifestyle now, Covid really changed things around and put things into perspective for people who live in big cities. 

Where do you see your team in the next 5 years?

I think the sky is the limit for the JDRE Team! We have big plans to continue to grow our digital presence, attend more events, and continue to stay innovative. I can’t wait to see where we are in 5 years! 

What makes you stand out from the competition?

When I moved to Hood River, I immediately noticed the need for something new and fresh in the Real Estate industry. I was searching for a home for my family and was so disappointed in the photos and presentation in the listings that were available. There were no modern staging companies, signage was dated, listing photos were taken with a cellphone, etc. I decided that I wanted to elevate the Real Estate experience for buyers and sellers alike. I rented a 1500 square foot warehouse and filled it with modern furniture and decor, bought a trailer, and started staging all the homes I would sell. The response has been amazing! 

What piece of advice would you give someone looking to get into the field or just up their sales?

I recommend that everyone that has an interest in getting their license shadow a licensed agent and get an idea what a day in the life is like. There is a perception that Real Estate is an easy way to make money, and that is not the case.  Yes, if you have a passion for people and a talent for negotiating…you could do really well, but if you are just in it for the money, it will be obvious to your clients. 

For agents looking to increase their sales, I would recommend doing an analysis of where your business has come from over the last 12 months. Once you know what your biggest lead sources are, you can come up with a plan to nurture those sources and increase your leads. I also recommend that every agent, no matter how seasoned, have a mentor. I have several mentors and coaches and I wouldn’t be where I am without them. 

What is your work/life balance and is it a company culture as well?

Work/life balance is very important to me. I have two young children and making them a priority means putting boundaries around my family time. I am unavailable for work calls between 5-8pm and take every Friday-Sunday off of work.  Just the same goes for my team and their families. “Family first” is what we always say. We have each other’s back and if someone needs time off, we all jump in to cover for them. We are a very tight knit team. I am so proud of the culture we have built. 

What inspires you?

I am inspired by other women who have paved the way for female entrepreneurs like myself. Being a mentor is something I am very passionate about and I love to be support system and cheerleader for others that are interested in pursuing the career that I love so much. 


For more on Jen Dillard and her team, visit her Linktr.ee here.

Follow @JenDillardTeam on Instagram.

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