It can be daunting to be the “first.” But for Lynn Osmond, the new president and CEO of Choose Chicago, being the very first woman to helm the city’s official destination marketing organization is an exhilarating, once-in-a-lifetime opportunity. 

Just two and a half months into her new role, Osmond has hit the ground running, laser-focused on promoting the U.S.’s third-largest city on the national and global stage. And she is more than prepared to pull this mission off successfully. She possesses an intimate knowledge of the Windy City, its tourism and hospitality community and DMO following 25 years leading the Chicago Architecture Center (CAC) as president and CEO, and serving as a Choose Chicago board member. 

In fact, under Osmond’s leadership, the CAC grew from a $2.4 million operation in 1996, with an audience of 150,000, to a $25 million organization in 2019, with an audience of 700,000, making it one of the top cultural attractions in the city and the largest architecture center of its kind in the world.  

“With the Architecture Center, I had the opportunity to travel the world and understand firsthand the power of the Chicago brand,” Osmond says. “I also have the unique perspective that I was a partner of Choose Chicago, so I understand the needs and challenges of our members.”

TSNN had a chance to catch up with the dynamic leader to discuss her historic appointment, including the opportunities and challenges a post-pandemic landscape presents, how she plans to bring meeting and trade show business back to Chicago and how she and her team are working to create more diversity and equity within the organization. 

How did you find your way into the tourism and events industry, and what do you like most about it so far?  

I’ve actually been “selling” Chicago for 25 years, just focused on one part—architecture—of what makes Chicago an amazing place to work and play. Now, I have so much more to “sell” with the assets of an entire city.  I have been overwhelmed by how welcoming the industry has been. I have had the chance to attend several industry events, spoken with other DMO CEOs, and connected with people across the country. 

How does it feel to be the first female leader in the history of Choose Chicago, and what have your first few months on the job been like? 

Exhilarating is probably the best description of the first two months. Some people have asked me why join at this time—coming out of COVID—but I actually see that as an opportunity.  

COVID has reframed how we look at travel and tourism. The old adage “absence makes the heart grow fonder” is applicable for travel; we realized how much we missed that, so there is pent-up demand. People are looking for authentic experiences. It’s no longer just about “getting away,” but what travelers can learn about the place and themselves. With our 77 neighborhoods and rich culture and diversity, Chicago offers all of that and more.  

For me, being able to support Chicago’s tourism and hospitality community during recovery is an honor coupled with a deep sense of responsibility to make sure we deliver for our partners.   

As the country moves out of the pandemic, what are your plans for bringing business travel back to the city, specifically trade shows and corporate events? 

Chicago is a great city for business. We have found that there is a significant pent-up demand for trade shows and corporate events. For example, the American Society of Clinical Oncologists (ASCO), was back in Chicago for the first time in two years last month. This show was almost at 2019 numbers. The International Manufacturing Technology Show (IMTS) is estimating more than 100,000 people for this September, and 45,000 hotel rooms have already been booked. Our convention center and meeting venues are busy!

However, the early success does not mean we are slowing down. From our central location to the diversity of meeting venues, the hotel stock, two airports, plus easy train and car access, Chicago is in a great position to compete. 

While gender diversity in executive roles within the destination marketing industry has been gradually shifting in a more equitable direction, what are you seeing as the biggest challenges of being a female leader in a historically male-dominated industry?  

This is not my first time being a woman in a male-dominated industry. In 2020, only 17% of architects were women, and that was an increase from past years. The challenges that women face are not new. As women, we need to be more prepared and ready to advocate more strongly for our position. We also need to be resilient and persistent. And finally, more often than not, we have to work harder and be smarter in order to earn the respect of our colleagues. 

What qualities do women bring to executive roles that empower them to excel at their jobs? 

Women are, in general, natural problem-solvers. We are also very collaborative. Throw in the ability to multi-task, and you have an outstanding leader.

What are your plans to foster more DEI within your organization as well as the tourism and events industry throughout the destination?

Chicago is an incredibly diverse city, and we need to make sure that diversity is represented within our industry. Choose Chicago has been extremely aggressive in this area, and it was one of the things I championed when I was on the board. Now, as the CEO, it will continue to be a focus area for our organization. 

We are looking at diversity in a few ways. One, our partners—I’m glad to say that nearly a third of our new partners this year were women and minority-owned businesses. Two, we need to foster diverse leaders. A few months ago, we named our first Equity Diversity Inclusion (EDI) fellow. This is a new program designed to support diverse talent grown into leadership roles. And three, within our own organization. We have an initiative, Choose Compassion, that is working specifically on this effort. 

These are just the start. There is much more to do and more opportunities for growth.

What advice would you give to women following leadership paths in destination marketing?  

Be persistent and follow your vision. When I first moved to Chicago, it was to lead the Chicago Architecture Foundation. But I knew we could be more than a foundation, but as a doorway to illustrate the impact of design. Today, it is the Chicago Architecture Center, a stand-alone location featuring more than 50 unique walking, boat and bus tours with 7,000 departures each year. It took 25 years to achieve all of this, but I stayed focused on my vision for the organization. 

Considering your extensive time at your previous job, you must be passionate about architecture. What are your top three architectural experiences that event groups should experience when visiting Chicago? 

That is a tough question! I have to start with the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady River Cruise. Not only do you have the chance to see Chicago from an entirely different perspective from the river, you also can see how Chicago’s architecture evolved over time. Other great options are the Art Deco Walking Tour or experiencing Chicago’s architecture from above from either the Skydeck at Willis Tower or 360 Chicago at the John Hancock Tower.

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