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Inclusive Cultures & Infrastructure: Retiring Wisconsin State Fair CEO Reflects on Fairs & The Fair Industry
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Kathleen O'Leary, CEO and Executive Director of Wisconsin State Fair Park retired from state service at the end of October. The State Fair Park board has appointed Shari Black, Director of Events, to serve as Interim CEO and Executive Director while the board conducts a national search for the next CEO/Executive Director of this iconic Midwestern fair.

O'Leary retires after 24 years in various management roles at the fair and held the position of Chief Operating Officer prior to taking the helm of the fair, but it's her unique trajectory that makes her story standout compared to other fair managers who assumed their position under less extraordinary circumstances. O'Leary has broken the glass ceiling – she's the first woman fair manager of the Wisconsin State Fair, which in 2019 was ranked #15 in attendance by Carnival Warehouse in 2019,  and one of the largest fairs to be managed by a female fair manager in the North America.

Under her leadership the fair sustained attendance of 1 million people, setting consecutive attendance records in 2017 & 2018. She steered the fair through 2020 by creating Wisconsin State Fair Alternatives, a series of events whose centerpiece was a Fair Drive Thru featuring a dozen different but familiar food vendor. This year, the fair returned, with a healthy turnout of 841,074.  “We have an overwhelming amount of gratitude for the opportunity to have hosted the 170th Wisconsin State Fair and celebrate everything we should be so proud of in our great state,” said O'Leary. “Seeing smiling faces enter our gates again after 724 days was a tremendous accomplishment for our staff, vendors, exhibitors, and board of directors.”

Before departing for the green pastures of retirement, O'Leary spent some time with Carnival Warehouse to discuss her distinctive career and the industry that she loves.

Carnival Warehouse: What is your favorite thing about the Wisconsin State Fair?

Kathleen O'Leary: I love the fair. It's a showcase of everything we should be so proud of in Wisconsin. I take pride in the agricultural showcase without question, but especially in our Commodity Pavilion, which has all the products grown from all over the state. It educates, but in a deeper way, it is experiential., You feel the pride of all the exhibitors, whether they're showing an animal, or the jams and jellies. It's where everybody comes to celebrate Wisconsin every year, and it's an absolute joy.

CW: You have a very unique trajectory – you became the first woman to be the state fair CEO, assuming this role after a very public financial scandal involving your predecessor – then after leading the fair to consecutive record-breaking summers, you became the first WSF CEO to face a global pandemic. How do feel now looking back at this crazy ride?

KO: My first step (as interim CEO/ED) was we have to be totally transparent and really mitigate the controversy. Taking all of that head on in 2016, and with only 78 days to opening day of a fair that was now attracting more than a million people is a testament and accomplishment that was only possible because of the staff and our partners. We also continued to make improvements, such as the Wonder-Fair Wheel, which has been great collaboration with Michael Wood. We also have added the metal detectors. We raised the bar on safety and security. I think the most important thing that I learned was that there is the need to make adjustments and knowing that one decisions impacts a lot of other decisions. In 2019, our sponsorships were at a record high, and we had some internal reorganization, changing management and staffing. Then the pandemic hit, forcing us to cancel for only the sixth time since our history (the first Wisconsin State Fair was held in 1851), and it required some innovative thinking so we could be financially sound and stable through those dark times, so we can make sure we were opening our gates and 2021 was a safe and successful fair. The ride was crazy, and any dull moments were only a small window of time.

CW: Was becoming the first woman CEO/ED of the WSF important to you?  

KO: I am so proud of it to be part of my legacy. We need women leaders in all industries, there are an ever growing number of female professionals in the fair industry and at exec levels of management, and it proved that with the right leadership we can have a successful fair. It was not controversial when I was appointed, I think we had moved beyond it being controversy, which is a testament to the fair. But people who had watched my career were elated that I was face of the fair for a number of years. I've always been very upfront about how much I believe, in the fair industry as a whole, the IAFE and the Wisconsin State Fair.

CW: Have you mentored any young women entering the fair and event/facility management profession?

KO: The answer is absolutely yes. I pride myself being a mentor to young women, and men, who have  advanced through IAFE. I am very proud of that as I pass the baton to Sheri Black, who has been associated with the fair since 2015. I love seeing women becoming part of the C-suite (CEO, COO, etc.) and I am very prod there will be yet another female as interim CEO.

CW: What were the barriers that you faced that the newest generation of women fair professionals don't have to, and which ones still exist?

KO: Early on, this was very much a male dominated industry and in the 24 years I've been involved with the fair, that has changed. There are so many women now taking on exec level positions, and they're continuing to have a seat at the table. Young people, especially young women, are starting out and advancing quickly to executive levels. The YPI (Young Professionals Initiative) at IAFE has been really important.  

CW: What advice would you give young people interested in the becoming fair managers?

KO: The fair industry has so many opportunities. It's an industry that will give you joy, advancement, flexibility. Stay passionate! .Stay passionate to your county fairs, to your state fairs, and your local fairs. I have such a grateful heart for all the people at the IAFE and the OABA who have helped me.

CW: You head not just one of the largest fairs in North America, but one that has grown under your leadership. What's your secret?

KO: In order to be successful, we need a very inclusive culture. Together we make all the difference, so all voices should be heard, listened to, and more than that, affirm people when they do good things, If you empower people they do well, and when you hold people accountable, its more reason for them to do really well. No department is better than any other department, you don't want to be so caught up in marketing that it becomes more important than facilities. It order to succeed, we need to rely on each other, we all play incredibly important roles. Respecting each other and the roles we play is most important. We can never become complacent, there's always room to improve.

CW: Were there specific segments of the fair that you identified as under-performing or were the changes you implemented more global in nature?

KO: Like other fairgrounds, we have an aging entity and the biggest need is infrastructure. We just completed a $4 million infrastructure project, with new streets and ADA-compliant buildings at the heart of the fair, which is so much better for visitors. Instead of just asphalting over the fairground, we created a Central Mall, so visitors can better enjoy their time there.

CW: What will you miss the most about being a fair manager?

KO: The people, and that's all encompassing, all our sponsors, exhibitors, the vendors, and partners. And of course, our fair's wonderful staff.

CW: What will you miss the least? 

KO: The politics.

CW: What is your favorite midway ride?

KO: Picking my favorite ride is like picking my favorite child. Watching everyone in Spin City enjoy the rides, persons from every ethnic background having an enjoyable time, riding the rides for hours, it's a joy. I do make a point of riding the rides. Dawn B. Crim (Secretary of the Wisconsin State Department of Safety & Professional Services) comes out before the fair and we ride all the rides together after they've passed inspection. I love that, it's always a great day.

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