Candidate Spotlight

CCIM Candidate Spotlight: Melissa Ray Gentry


After a career as an archaeologist and starting a family with her husband, Melissa Ray Gentry returned to her hometown of Billings, Mont. While raising her new family, she earned her real estate license in January 2020, following in the footsteps of her father Jerry Ray, CCIM, who had built a business as a real estate agent and developer.

But after less than a year as father-daughter colleagues, Jerry fell ill with COVID-19 in November 2020 and soon passed away. Leaving his commercial real estate practice to Melissa, she was thrown in the deep end of the pool, dealing with tenants, building maintenance, depreciation schedules, and plenty of other considerations for her to learn on the fly. Now, nearly two years after that tragic loss, Gentry views her business as a way to honor her father. And just like him, she has now started her journey to earning the CCIM Designation.

After taking the CI 101 course, Gentry came across the portfolio her father used to earn the pin — complete with a personal narrative about each of his 20 transactions. While understanding the business more through education, she also values the process to see another side of her dad. Commercial Investment Real Estate magazine spoke to Gentry about starting her path to the pin, which she hopes to earn by 2025.

CIRE: What does it mean to you to follow in your father's footsteps toward the Designation?

Melissa Ray Gentry: It means so much to me on many levels. I feel like I am getting to know him as a savvy investor. People said he had the Midas touch — he had such an ability to see the potential in locations and buildings. I see the thriving business he created through knowledge gained from CCIM Institute. He taught me to think things through, tell the truth, and always run the numbers. He had a favorite quote about investing, “You need bucks, brains, and courage.” Isn’t that the truth about being a real estate agent and investor?

My father always wanted me to be both a CCIM and a broker. I believe the best investment one can make is in themselves. Learning how to financially analyze real estate is how my father built our family’s CRE business. I aim to expand our business, and I know the CCIM coursework will be my guide.

CIRE: Have you been able to put your education to use? How has the Designation curriculum impacted your professional abilities?

Gentry: Shortly after I completed CI 101, I represented both sides in a seller finance deal. I was asked to run the numbers at different interest rates with varying balloon payments. Armed with my knowledge from the class, I put together the deal with ease and confidence. The class also helped me understand the inheritance basis of my father’s assets. I’m currently looking to sell one of his Class C buildings and 1031 exchange the sale proceeds into a Class A building. The information I received on how to determine cost recovery, adjusted basis, and capital gains has been tremendously useful to me — and I know it will be just as useful to future clients.

CIRE: What has been the most challenging aspect of your journey toward CCIM Designation?

Gentry: Taking the time to take the classes. In managing the family business, I represent tenants, buyers, and sellers. I am also a wife and mother. I realized that to say yes to achieving my CCIM Designation, I needed to start saying no to some real estate pulls on my attention. 

CIRE: What support structures have helped you during this process? Have you received help from colleagues, mentor figures, etc.? Is there a CCIM who inspires you?

Gentry: My husband, Bryan, has been a huge support for me and has helped me every step of the way in managing our CRE business. There are many other seasoned CRE agents in my area who have been helpful as well. Travis Dimond, the vice president of Berkshire Hathaway here in Billings, Mont., has been the most inspiring commercial real estate agent I have met so far. His knowledge of the market and openness to communicate has been a huge asset to me. 

I believe the best investment one can make is in themselves. Learning how to financially analyze real estate is how my father built our family’s CRE business.

CIRE: As a CRE professional in Montana, what unique challenges do you face in a primarily rural market? What do you appreciate most about working in Big Sky Country? 

Gentry: The biggest challenge as a CRE professional is just keeping up with the pace of business. Our state stayed open during the pandemic. All aspects of the Billings real estate market exploded. Businesses and people flocked here. I have been contacted by multiple health care providers and industries looking to get a foothold in our market. I signed three leases in one day at the height of the leasing activity.

What do I appreciate the most about working in the Big Sky? I love the people here — they are salt of the earth and hardworking. I love watching my hometown grow into a thriving economy. I love being a part of that growth by offering quality commercial space at a competitive rate. 

CIRE: Is there one particular deal that has been especially interesting or unique in your recent career? What made it so special or interesting? What lessons did you learn?

Gentry: We had about 4,500 sf of retail space on a busy street that had been vacant for years. My father had been adamant to not reduce it down due to parking concerns and splitting of utilities. He just knew someone would need that size of a space. The smaller retail spaces were leasing up quickly, but no one was biting on this property. I had shown the space multiple times. Then one day, the eventual tenant breezed in and loved every part of the large space — it was exactly what she needed. Less than 48 hours later, we signed a long-term lease. I learned that real estate can be a roller coaster and to not give up, always trust your instinct, don’t take things personally, or get discouraged. You might be one phone call away from a tremendous deal!

For more on the CCIM Designation process and curriculum, visit  Earning the CCIM Designation.

Nicholas Leider

Nicholas Leider is senior content editor for Commercial Investment Real Estate. Contact him at

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