Women at the Helm: Lynn Osmond, CEO, Choose Chicago

August 1, 2022

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 partarchitectureof 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 timecoming out of COVIDbut 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 partnersI’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.

 

Don’t miss any event-related news: Sign up for our weekly e-newsletter HERE, listen to our latest podcast HERE and engage with us on Twitter, Facebook, LinkedIn and Instagram!

Add new comment

Partner Voices
Just when it seems like Las Vegas can’t get any bigger, brighter or more exciting for groups, MGM Resorts raises the bar again. The company continues to invest and innovate across its portfolio of Las Vegas resorts, with new attractions and upgraded experiences for attendees of all interests.  Remodeled Guest Rooms MGM Grand is the largest single hotel in the world with over 5,000 guest rooms and an 850,000-square-foot conference center. It is home to the newly remodeled MGM Grand Studio Tower—700 reimagined guest rooms with a fun mid-century vibe. Nearby, the iconic New York-New York Las Vegas Hotel & Casino recently completed a $63M redesign and remodel of its 1,830 guest rooms and 155 suites. Down the street, Bellagio Las Vegas is sporting renovated rooms in the Spa Tower with sunrise-inspired decor and luxurious soaking tubs in Premier King rooms after a $110-million transformation. Reinvented Luxury Experiences The Luxury Meetings District, made up of Bellagio Las Vegas, ARIA Resort & Casino, Vdara Hotel & Spa, The Cosmopolitan of Las Vegas, Park MGM and NoMad Las Vegas, is now more connected than ever before. A new interior walkway opened this October for a seamless attendee experience – connecting Vdara, Bellagio, and The Cosmopolitan of Las Vegas, guests can now walk from Park MGM to Bellagio in around 15 minutes. New on the scene in the Luxury Meetings District is Cathedrale at ARIA, TAO Group’s upscale establishment specializing in exquisite French-Mediterranean cuisine offering elevated private dining experiences that opened in May. Heralded by World’s Best 50 Restaurants, GQ and VOGUE, LPM at The Cosmopolitan of Las Vegas is opening this fall and will deliver its signature spontaneity and imaginative celebration of France’s Mediterranean cuisine, art, and culture to the unique luxury resort in impeccable fashion.  A “New Wave  for Mandalay Bay A new wave of enhancements and experiences has arrived at Mandalay Bay Resort and Casino, including Flanker Kitchen + Sports Bar, an 8,445-square-foot restaurant that opened this June, perfect for pre- and post-game eats and drinks. Event planner’s favorite, Chef Michael Mina’s StripSteak, received a full renovation and now includes one of the largest private dining rooms on The Strip. Retro by Voltaggio debuts a one-year residency with a fun take on pop culture of the 80s and 90s with classic American dishes. An exciting addition planned for 2024 is Swingers, a 40,000-square-foot oasis of street food, miniature golf and art at Mandalay Bay. Most exciting for meeting planners, the 2.1 million-square-foot Mandalay Bay Convention Center  is undergoing a complete refresh, with lightened space, added eye-catching art, and improved technology infrastructure for even more flexible space. Energy-efficient digital signage now leads the way with faster internet speeds and new AV options. From renovated guest rooms and meeting spaces to celebrated dining options and dedicated teams, MGM Resorts is dedicated to delivering exceptional and innovative meeting experiences.