Doug & Diane Oberhelman

The Ultimate Power Couple

Having traveled the world meeting executives and heads of state, they remain firmly committed to central Illinois, where their leadership is second to none.

Doug and Diane Oberhelman
Photography by David Vernon

The 50,000-square-foot Caterpillar Visitors Center in Downtown Peoria bears his name, a slew of sustainability features paralleling his passion for conservation and the environment. Across the river, the sleek, glass-and-steel structure overlooking I-74 from high atop the bluffs of East Peoria bears hers—the headquarters of Cullinan Properties. Doug Oberhelman and Diane Cullinan Oberhelman have traveled the world meeting executives and heads of state, but here in Peoria—her hometown and his adopted one—they’re known simply as “Doug and Diane.”

A Caterpillar man through and through, Doug spent his entire 41-year career with the earthmoving and construction giant, working his way up from an entry-level finance position to eventually become chairman and CEO. He led the company from 2010 to 2017, through unprecedented global economic conditions and a complete restructuring of its major businesses. Since his retirement, he’s remained active on a variety of boards, managing his investments, hunting and fishing, and working on his golf game. 

A native of Peoria, Diane has had a lifelong fascination with buildings and construction. She started her real estate career with Jim Maloof Realtor in the early 1980s before launching her own firm in 1988. Since founding Cullinan Properties, Ltd., she has grown the company into a leading provider of real estate development and acquisitions—with nearly $1 billion in projects completed to date—and remains its chairman and founding partner. 

Together, this dynamic couple remains firmly committed to the Peoria area, investing in local companies and projects and spending time with their children, grandchildren and extended family on their farm in rural Peoria County. They also believe in giving back to their community, focusing their philanthropic efforts in the areas of conservation, education, cancer research and children with disabilities. 

Diane, your family has a long, rich history in central Illinois. Tell us about that and how your parents impacted you. 
Diane:
I am a lifelong Peorian and love the Greater Peoria area. We will forever call Peoria home! My parents were always great, active advocates for Peoria, and involved in volunteer efforts and politics as well. Their grandparents emigrated from Germany and England, and luckily my parents ended up here. How that happened is quite a special story in and of itself. 

Sadly, my mother, Tilley, just passed away late last year and is greatly missed by all. My dad, Fred Allen, is still alive and a brilliant man at 96 years of age. He’s a retired attorney, and we are grateful he still shares his wisdom and free advice with family and friends! My parents raised us to work hard, build a strong team, give back to our community, and treat others as we would want to be treated. That, along with putting our persistent and great efforts into everything we do, ensured things would always work out well!

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Diane and Doug Oberhelman look over plans for their property in rural Peoria County, where they have hosted First Lady Laura Bush and other leaders from business and government.

What were your hobbies growing up? 
Diane:
My hobbies as a child involved horseback riding, golf, raising fish, swimming, volunteering, studying the planets and all the new spaceships and space initiatives, basketball and tennis. I also really enjoyed my microscope and tried to look at so many things through it. I liked working around our neighborhood as a small child, helping some of the older neighbors with their yards. Official sports for girls just started when I was a freshman in high school; therefore, I signed up for many sports at Richwoods High School. Those were amazing, changing times in 1972!

What were some of your earliest ambitions? 
Diane:
I told my dad when I was very little that I wanted to make a big difference in the world. He always reminds me of that to this day. I was fascinated with buildings and construction at a young age, and I was intrigued by people all over the world who made such a difference for the countries in which they lived with their projects.

Doug, let’s talk a little about your childhood. What did you like to do as a kid? 
Doug:
From about seven years old through high school, I lived in Woodstock, Illinois—a small rural community at the time, northwest of Chicago. It was a great place and I was involved in Boy Scouts, reaching “Life” status, as I recall. I also had a paper route for the local paper and the Chicago Tribune, all on my Schwinn bikes. I went through several of them delivering all those papers year-round, before and after school. I had various other jobs as well, including rolling pizzas for a tavern, mowing about 20 yards a week, and being a scorekeeper for the local Little League. I was always busy and used the money I earned for college and investing in stocks at a very early age. I left Woodstock for Millikin University and came directly to Caterpillar and Peoria after graduation in 1975. 

When did you know that you wanted to work for Caterpillar? 
Doug:
I didn’t know I wanted to work for Cat until college recruitment, but my father was a John Deere salesman at a local dealer, so I was always around machinery, mowers and engines, doing something or other. 

What were your ambitions when you started at Caterpillar? Did you ever think you would end up leading the company?
Doug:
When I started as a finance analyst in 1975, I’m not sure I knew what a CEO did, but I was ambitious and really enjoyed the work and traveling internationally. My second job was trading foreign currencies around the world, and at 25, I thought that was interesting. The U.S. dollar had just floated a few years earlier and the gold standard had been released, so trading currencies was new and fun and introduced me to a brand-new world. From there, my interest was truly international finance, which led me all over the world. I’m very proud of living on multiple continents and traveling to about 70 countries over my career. It was always a learning experience. 

Diane, what led you to go out on your own and found Cullinan Properties? Did you have any experience running a business?
Diane:
When I founded Cullinan Properties in 1988, it was after having been in the real estate industry for many years. Our growth was very much a team effort with the initial members, as we worked to create a new approach to real estate development and brokerage by managing all facets of every deal and having a broad mixed-use focus. It was much harder work than we anticipated, with many regulations and requirements that go along with starting a new business, and that really took time and money away from our core business initially. The Peoria area was stable, yet not booming. We were able to be very successful from even our first year, due to how diversified we were in developing commercial buildings and residential subdivisions. No doubt, it was and is hard work!

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Doug and Diane live on a small farm in rural Peoria County where they raise chickens, organic beef cows and a few horses.

You were diagnosed with breast cancer when you were just 36 years old. Describe that journey—how you coped and survived, and its impact on you and your family.
Diane:
When I was diagnosed with breast cancer, it was a very difficult time for my immediate family and friends, as well as my extended family at Cullinan Properties. I was devastated that I had disappointed everyone and let them down, and that I would have to go through treatments and take time away from them. I thank God for all the support from family, friends, coworkers and Peoria physicians who got me through that. 

I am now stronger than ever, almost 25 years later. About the time I was diagnosed, my dad had recently retired. Therefore, he and my mom and then-husband Mike were helping daily with our four children, providing love and support, and shuttling them to and from all their activities. Kathleen, Maureen, Alison and Allen were in high school and grade school at the time, so you can imagine it was very busy. I am a very lucky person and even wrote a book with Joy Miller and Monica Vest Wheeler called Cancer - Here’s How You Can Help Me Cope & Survive, to help other people and families who are going through cancer. 

What was the biggest challenge you have faced during your career in real estate, and how did you handle it? 
Diane:
Our hard-working Cullinan Properties team works even harder to overcome challenges. There indeed is no “I” in TEAM, and the passion we collectively share for our projects and the clients we work with have contributed to our success. The recent recession and constantly changing product mix, on account of the changing retail climate, have certainly been challenges we’ve faced. Our team has managed to turn them into a positive! We were one of the first real estate companies nationally to have developed mixed-use projects (which includes apartments, office buildings, medical buildings, VA buildings, government, industrial, student housing, etc.) over 30 years ago. That diversification and creativity has made Cullinan Properties stronger in times of economic turbulence. 

What about you, Doug? What was the biggest challenge you faced as CEO? 
Doug:
The biggest challenge I faced was an unprecedented four-year slowdown in global sales, which was the slowing of the Chinese economy and its impact felt around the world. That led to multiple restructurings, layoffs and plant closings. This was a very difficult period for all of us on the management team. I guess the silver lining was that we never lost our credit rating, didn’t lose any money, and continued to increase the dividend slightly. While this didn’t alleviate the pain felt by so many employees who were impacted, it did set Caterpillar up for the record results and share price achieved shortly after I retired. We all felt better about that.

What accomplishments are you most proud of in your career?
Doug:
Obviously I’m most proud of being named chairman and CEO in 2009 of one of the world’s great companies. I was also pleased to completely restructure the company in 2010 into the major businesses and watch the very positive results occur over the years. Mostly, I’m proud of the company and its employees that do so many good things for so many around the world. 

What development projects are you most proud of, Diane?
Diane:
Our four children, sons-in-law, daughter-in-law and 10 grandchildren, by far! From a professional standpoint, however, the Cullinan Properties team has created many life-changing experiences for communities across the country, from Illinois to Texas and in between. I am so proud of ground-up projects like the Shoppes at Grand Prairie and the surrounding development, and East Peoria’s Levee District. Outside the Peoria region, St. Louis is a very active market for us, due in large part to our success with Streets of St. Charles. We built what was the country’s largest Veterans Affairs outpatient clinic in Austin, Texas in 2012, and are poised to create another successful mixed-use development, Rock Run Crossings, in Joliet, Illinois. I and the Cullinan team have much to be proud of!

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Doug and Diane enjoy spending time with family and in the outdoors, hunting and riding their horses.

What was your life like when Doug was CEO of a Fortune 50 company? How were you able to balance your time with him when he was traveling around the world? 
Diane:
Life with Doug has been enriching and I am very proud of him. Before we met, I was always either in my hometown Peoria region or at a project, and I had never traveled the world or met so many Fortune 100 executives or heads of state of many countries. I truly believe it brought many benefits to our children, who were able to meet so many people, making them so much more worldly. Doug made a huge difference with Caterpillar, Caterpillar dealers and many suppliers and projects. He is and was truly a gamechanger for Caterpillar, and it was a pleasure watching him in action! 

Doug, how did you feel when the Caterpillar Visitors Center was renamed in your honor? 
Doug:
I was overwhelmed when Cat announced the naming of the Doug Oberhelman Caterpillar Visitor Center at my retirement party in 2017. It’s quite an honor, but I will say I was just one of several Caterpillar CEOs who made that happen over a long period of time. 

What has kept you busy since then?
Doug:
Retirement the last two years has been great. I’ve been busy, but not tied to the calendar “anchor” that everyone has while they’re working. I’m involved with several boards, including ExxonMobil, Bombardier, Kiewit, and several private companies and charitable groups. I’ve also been active in investing and trying to find good, small manufacturing companies—primarily in Illinois—to buy or invest in. That has been very enjoyable. Of course, I have many outdoor activities, including hunting and fishing, and I’m always trying to improve my golf game, which is perhaps the biggest lifetime challenge!

Doug, you have a longstanding interest in environment issues and the outdoors. Tell us about that. How did it impact your leadership at Cat? 
Doug:
Diane and I are both passionate about conservation and the environment and even wrote a book about conserving one of our properties, a former coal mine. I am also very active with Wetlands America Trust, which holds all the conservation easements for Ducks Unlimited and is very active in wetlands management. Caterpillar has always been supportive of conservation, so as CEO I was able to promote that and sponsor several programs for our dealers and customers. 

oberhelman quoteWhen and how did the two of you first meet? 
Diane:
It’s an interesting story, as several of our joint friends were trying to get us together. We really didn’t know each other, as Doug had been living out of the country off and on over his career and wasn’t from Peoria. The best matchmaker we had was Sylvia Fites [the late wife of former Caterpillar CEO Don Fites] who was determined to introduce us, and she did! 

Doug: Ralph Converse, who I had known when he was with IBM and later was president of Diane’s company, was another. He and his wife Jane hosted a beautiful boat ride one afternoon on the Illinois River. And now, 19 years later, the rest is history. 

What is your favorite memory as a couple?
Diane:
Our best memory is our very small wedding in Green Lake, Wisconsin, in a farmhouse built in 1847 that has been owned by my dad’s family continually since then. We have great memories of that weekend and the annual July 4th holiday there. 

What do you like to do together? What activities do you bond over?
Doug:
We both like to spend time with Diane’s family, and with such a large number, there’s always something going on. We like to spend time outdoors and enjoy hunting and riding our horses. 

What is something most people do not know about you? 
Diane:
We have a large garden and make spicy dill pickles every year. We also raise organic vegetables and live on a small farm where we raise chickens, organic beef cows and a few horses. 

Tell me about your community involvement in the Peoria area. What causes are near and dear to you? 
Doug:
We are very involved in Peoria and have no plans to relocate, either for the winter or longer. Our support has been around activities to help cancer victims, conservation of the environment, and kids. Easterseals, the Cancer Center and various others have been our focus. 

What is your vision for the future of Peoria? 
Diane:
We see a vibrant Peoria that is a little down on itself right now. However, the local economy is strong, Caterpillar is stable and adding jobs, and the airport is seeing record travel numbers. Some reimagining, combined with some broader Peoria-area activities supported across the region, would draw a larger picture of this great community. 

What would you like to be your legacy as a couple? 
Doug:
We are focused on the legacy of leaving the Peoria area a better place than we found it and the legacy our children and grandchildren help lead down the line, as we certainly will support causes, issues and developments we believe in. There are many. PM

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