Raised on his family’s multigenerational farm in East Troy, Wisconsin, Todd O’Leary found a passion for hospitality early in life.
While pursuing a career in travel and tourism was not part of his original vision, a chance college road trip with a friend put him on the path. Through serendipity and strategy, O’Leary evolved a rewarding career promoting Milwaukee, San Francisco, and Sonoma County, California to the world. Along the way, he has earned acclaim including recognition in 2022 as one of the Top 25 ‘Extraordinary Minds’ in the industry by Hospitality, Sales, and Marketing Association International (HSMAI). In April 2024, he was appointed President and CEO of Visit Alexandria, the destination marketing organization (DMO) for the City of Alexandria, Virginia. Here, from the heart, is O’Leary’s continuing journey of people and places..
Tell me about your Midwest upbringing.
Life was uncomplicated and happy on the farm. I grew up feeding our cattle, bailing hay, participating in 4-H learning programs, and other classic farm kid activities. My aunts, uncles, cousins, and other extended family members all lived close by. We were always together for fun, birthdays, church, potluck dinners, and more. Those gatherings instilled in me a powerful sense of community, which along with the values of working hard and treating people right, came to define what I most believe in and who I am today.
That is very admirable awareness for a youngster.
An early mentor, a successful restaurateur in Milwaukee, told me that while any one can cook or wait tables, he always hired people who had a heart for hospitality. Baked into my own heart as a child, that resonated deeply with me. Throughout my career, I have likewise always sought to hire like-hearted people.
What preceded travel and tourism for you?
While passionate about hospitality, it was not a career aspiration at first. Initially drawn to the idea of marketing, I pursued a degree in urban planning and marketing at the University of Wisconsin-Whitewater. In my junior year, a friend asked me to ride with her to the University of Wisconsin–Madison, where she was interviewing for Disney’s College Training Program. She wanted company, so I went along. At her suggestion, I also interviewed with the Disney folks. One month later, I received an offer letter for a summer internship at Walt Disney World in Orlando.
The mouse that roared!
That road trip changed the trajectory of my life. Uprooting from rural Wisconsin to the Magic Kingdom for the summer of 1997 opened my eyes to the tourism industry at the highest level. After completing the program, I knew that I was not quite a theme park guy, but I was now open to new ideas, like product marketing. Heading into my senior year, fortune visited again when I caught Bill Hanbury, then president of the Greater Milwaukee Convention & Visitors Bureau (CVB), talking on TV about the blockbuster summer ahead. The city, just 30-plus miles from East Troy, was opening a new convention center, celebrating hometown company Harley-Davidson’s 95th anniversary, and hosting the National Governors Association’s annual meeting.
Another big rev up of inspiration.
It certainly got my attention. I sent the CVB my resume and cover letter, mentioning the TV interview, and scored a summer internship in public relations. I knew little about the CVB’s work or the field of public relations, but like my friends said, I hit the jackpot with those three events in the summer of 1998. The Harley-Davidson party drew record attendance, I met the Mayor and Governor of Wisconsin, connected with business owners and much more. Bitten by the bug, I graduated, joined the CVB as a tourism assistant, and have never looked back.
How uplifting to find the path for which you were clearly destined.
It truly was, and once on that path, I took control of my future with a series of intentional moves. In 2005, following seven-plus years managing group tours for the CVB, I gave the aviation industry a go as Senior Sales Manager for Milwaukee-based independent carrier Midwest Airlines. The experience was great, but I missed the CVB, which had been renamed VISIT Milwaukee in 2005. Returning in 2008, I spent another seven-plus years with the organization, first as Director of Membership and then as Director of Marketing. Milwaukee was home, but my boss was not going anywhere, and with a ladder still to climb, I joined the San Francisco Travel Association in 2013 as vice president of partnerships before moving up to vice president for global partnerships and strategic alliances.
What attracted you to San Francisco in particular?
Several factors. Promoting a Tier 1 city that had big budgets and big plans to the world was highly appealing. Major events were coming, including Super Bowl 50 in 2016 and the 50th anniversary celebration of the Summer of Love in 2017. As a gay man, San Francisco was naturally compelling. I was in my lane, moving up, and spent five memorable years working for a DMO that offered the highest level of engagement.
What prompted your subsequent lane change to Sonoma County?
Here is where I introduce my husband, Mark, who is also from Wisconsin. We met in Milwaukee in 2005 through a mutual friend. Celebrating our 20th anniversary year, we have supported each other every step of the way, including making career decisions together. When the role of vice president, marketing and communications became available at Sonoma County Tourism, we went for it. We loved wine from our Milwaukee days and frequented Sonoma and Napa wineries while in San Francisco. We had married in Sonoma County, at a beautiful destination wedding eight years earlier on Labor Day weekend. I accepted the job, and we spent five and a half special years living and working in the land of milk and honey. Then came time for our next big decision. The time had come in my career for a president/CEO role. I was ready. Encouraged by industry friends, I had been actively looking for some time. My next destination could not just be anywhere though, it had to be truly compelling for us to leave Sonoma.
Which is when Alexandria came on your radar?
Yes. In this industry, you follow all the cool programs and initiatives that your competitors and peers are undertaking. You learn about professional moves and destinations on the rise. In December 2023, my predecessor Patricia Washington announced her planned retirement after more than a decade as president and CEO of Visit Alexandria. I had been in Alexandria when I was much younger, but had little recollection of the city. Yet, Alexandria was compelling and checked all the boxes. I liked the city’s size and its proximity to the familiar dynamism of the Washington, D.C. metro area. Alexandria’s distinct identity was also appealing. Older than D.C, the city is not a suburb, but a place of history with its own original character and flavor. Mark and I discussed and considered the opportunity at length. It was a big cross-country move. We made the decision to go together, which made me love him more than ever.
Mark and Todd (Photo by Todd O’leary)
Two hearts beating as one. Did Mark also have a new opportunity?
Yes. Mark works in public health, and similar to his posts in California, he serves as the LGBTQ community liaison in Fairfax County’s health department, helping to connect people to the care they need. As we like to say, we both work for our community in different ways.
How is your big shift from the West Coast to the East Coast going so far?
Encountering our first true winter in more than 11 years, we had to break out our hats, gloves, big coats, and shovels again! But we are happy for springtime and the other seasons. When you move in my field, exploring new neighborhoods and meeting new people is exciting and fun. Our neighbors and the community have welcomed us with open arms, many baked goods, and other gifts, and the move has been positive in every way.
How are you approaching your leadership role?
By hitting the ground running and wasting no time in embarking on a strategic planning process for the future of Alexandria tourism, centered on how Visit Alexandria can best meet the needs of the local community. Like many peer organizations, our world changed during the pandemic. We made adjustments that were outside of our core mission. While in no way losing our way, it is critical to our importance and effectiveness as an organization that we regain our central focus as an asset to the community. Shepherding this process has been my biggest project to date as we prepare to present our five-year strategic plan to the board.
Tell us about Alexandria and its commitment to equality and inclusion.
We have our own story of equality, inclusivity, and welcome to tell, in the truest and broadest sense of the terms. Alexandria has earned a perfect score from the Human Rights Coalition on LGBTQ+ equality for the past five years. We proudly tell the stories of Alexandria’s rich Black history. Our ethos is all-welcoming. Hosting events like WorldPride reflects a doubling down on the values of this community.
How fitting then that you found a place with a heart of hospitality to complement your own.
Our decision to move to Alexandria has been positive in every way. Mark and I are happy here. I am looking forward to the board hopefully ratifying the new strategic plan. We are already planning a series of events leading up to the 250th anniversary of America’s independence in 2026, when D.C. and Alexandria will be in the spotlight. And that hospitality heartbeat remains my guide. As I have learned through the years, take care of the people in your immediate orbit and you will take care of your visitors and stakeholders.
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