On a cold Chicago morning, Wendy Schenker stood on Michigan Avenue in front of a sleigh, a line of sculpted reindeer and a Wintrust sign half-buried in artificial snow. She was there to explain a parade. Sister Sledge would ride a float. Santa would close the procession. Fireworks would rise above the river. People were being invited to wear their loudest holiday sweaters and help chase a record. The television reporter held the microphone; Schenker supplied the details with the practiced ease of somebody who understood that the details were the story.
Her formal job is Senior Vice President and Chief Marketing Officer at Wintrust Financial Corporation. Her more revealing former title was Chief Entertainment Officer. It could sound like corporate whimsy, the sort of phrase invented for a name badge and retired after lunch. In Schenker’s case it described real operating work. She has spent years connecting a bank - a business of rates, rules, deposits and careful disclosures - to the moments when Chicagoans leave the house and gather.
The premise is almost defiantly ordinary: a community bank should be visible in the community. But visibility is the easy part. Any company can buy a sign. Schenker’s public work suggests a harder standard. A sponsorship should give people something to do, should lower a barrier, should add energy to an institution the city already cares about. The logo arrives inside the experience. It does not have to interrupt it.
“We love the fact that this is a community event that’s free and everyone can come down and enjoy it at no cost.”Wendy Schenker on the Magnificent Mile Lights Festival
The useful work behind the fun title
Schenker’s route to the C-suite began with mass communications at the University of Denver. Public professional profiles place her earlier in marketing at the Center for Egg Options and as founder and owner of Wendy Schenker, LTD. Her name appears in Wintrust’s 2005 annual report, evidence of a relationship with the company stretching across two decades. By 2018, she was publicly identified as a Wintrust vice president of marketing. By 2025, the title had become Senior Vice President and Chief Marketing Officer.
The through line is experiential marketing: events, sports sponsorships and loyalty programs. These are disciplines built around repetition and behavior. People join a travel club, return to an annual festival, take their children to a match, recognize the sponsor, and slowly place that sponsor inside their mental map of a city. The work is less like publishing a single persuasive message and more like keeping a series of promises.
Even a small answer Schenker gave in 2018 reveals the mindset. Asked which travel-club destination never disappointed, she chose Italy. Then she got specific: southern Italy and Sicily, Rome, Florence, Venice, and the continuing appeal of Tuscany. This was not abstract “customer engagement.” It was knowing what a group wanted to revisit and why. Loyalty lives in those particulars.
people already value
with something to do
that carries the brand
That pattern helps explain why a holiday parade is not a frivolous assignment for a bank marketer. A regional financial institution has an unusual brand problem. Its products matter intensely, but customers would prefer not to think about most of them every day. A festival solves no financial problem. It does something else: it gives a distant institution a human scale. The bank becomes the reason the cheesecake is free, the fireworks happen, or the player can spend an afternoon with a young fan.
A coincidence becomes a partnership
When Wintrust became title sponsor of the Magnificent Mile Lights Festival in 2022, Schenker noticed an elegant coincidence. The festival was in its 31st year. Wintrust was, too. “Everything seemed to line up,” she said. The symmetry made a tidy talking point, but the fit underneath it mattered more. Here was a free, family-centered Chicago tradition with national broadcast reach, a riverfront fireworks finale and an afternoon built from small, welcoming acts.
Schenker spoke about the partnership in civic as well as promotional terms. The hotels were full. The restaurants were booked. The festival brought economic activity downtown. It was positive for the city. That frame expands the usual sponsorship equation. The bank gains awareness, certainly, but the district gains visitors and businesses gain customers. Families gain a free day out. A useful partnership makes the exchange visible from every side.
Her broadcasts from the festival are cheerful and concrete. She names the floats, musicians, mascots and food. She describes what a visitor will see. The language has almost none of the mist that can settle over corporate campaigns. It is a parade; come to the parade. It is free; bring everybody. The clarity is part of the craft.
+ 31
A story hidden in plain sight.
The matching anniversaries did not create the partnership, but they made its logic instantly repeatable. Strong brand narratives often begin with an operational fact somebody bothered to notice.
The “Chief Entertainment Officer” title makes more sense here. Entertainment is not merely decoration. It is an invitation architecture. A successful public event answers practical questions: Who can enter? What will hold a child’s attention? What happens at the end? What detail will a person mention on Monday? Those decisions turn a sponsorship package into a day people can picture before they arrive.
From the stands to the neighborhood
Sports sponsorship often stops at borrowed excitement: a logo near the field, hospitality seats, perhaps a commercial during the broadcast. Schenker’s work with Chicago Stars FC points toward a longer chain. In 2024, the club and Wintrust launched a player-driven community initiative. Players nominate and work with organizations that match their interests and the club’s values. The resulting programs connect professional athletes, nonprofits and people around Chicago.
The partnership’s community work has included youth clinics and programs involving organizations serving girls and women. The club’s current programming also combines access to soccer with leadership, teamwork and problem-solving. Schenker’s language stays close to purpose: creating opportunities for girls across Chicagoland to thrive, investing in the future of sport, and supporting the dreams of young athletes.
“Together we’re not just investing in the future of sport but in the dreams and aspirations of these young athletes. Let’s go Stars!”Wendy Schenker on Wintrust’s Chicago Stars FC partnership
That last burst - “Let’s go Stars!” - matters. It keeps the statement from becoming a grant memo. Schenker is speaking as an executive, a partner and a fan. The enthusiasm closes the distance between the institution writing a check and the people wearing the shirt.
Her nonprofit service fits the same pattern. When she joined Keshet’s board, Schenker was introduced as a marketer with strengths in events, sports sponsorships and loyalty programs. She also supplied a plain statement of belief: everyone has a responsibility to give back to people and places. The organization, which works toward inclusion for people with disabilities, described her intent to bring her professional knowledge to its mission.
There is a useful distinction here between community as a market and community as a practice. A market is counted. A practice requires showing up, doing the recurring work and sharing skills beyond the job that produced them. Schenker’s visible career sits where those two meanings meet. Her employer benefits when Chicago recognizes its name. The recognition carries more weight when people can attach that name to something they joined.
A career measured in returns
A long Wintrust association is visible
Schenker’s name appears in the company’s annual report personnel listings.
Marketing and loyalty
As vice president of marketing, she discusses what keeps Wintrust travel-club members coming back.
Events and service converge
She joins Keshet’s board and helps present Wintrust’s new title sponsorship of the Lights Festival.
A wider community stage
Broadcast appearances, sports programs and a promotion to CMO sharpen the public outline of her work.
In 2025, Schenker was among Wintrust leaders recognized by Crain’s Chicago Business in its People on the Move coverage. By then, the public title had caught up with the scope: Senior Vice President, Chief Marketing Officer. The promotion placed a conventional executive label over an unconventional body of work. Marketing remained bound to a city calendar - the festival, the season, the annual return.
This kind of career does not produce a single invention that can be held up for inspection. It produces a network. The Magnificent Mile Association, Chicago Stars FC, nonprofit partners, performers, players, families, broadcasters, bank colleagues. Schenker’s role is connective. The skill is finding an overlap sturdy enough that each participant can enter for a different reason and still leave feeling part of the same event.
That may be the most transferable idea in her work. Local marketing becomes credible through accumulated presence. A company cannot declare itself part of a city and expect the city to agree. It can support an event this year, improve it next year, connect it to another institution, open it to more people, and return again. Belonging is a compound return.
The invitation is the strategy
Banking will keep becoming more digital. Branches, apps, payment rails and service channels will keep changing. That makes physical public experiences more unusual, not less relevant. A parade cannot be reduced to a push notification. A child meeting a player is not a conversion event. The apparent inefficiency is part of what gives the moment its emotional weight.
Schenker’s public career offers no manifesto, and it does not need one. The actions form the argument. Choose partnerships with local meaning. Make entry easy. Give people a reason to participate. Pay attention to the memorable particulars. Connect the sponsorship to economic and social value beyond the sponsor. Then return.
Back on Michigan Avenue, the artificial snow, the reindeer and the branded sign could have looked like props in search of a message. Schenker made them a preview instead. She told viewers what would happen, who would be there, and why they might want to join. For a few minutes, a bank executive’s job was to explain where Santa would sit.
There are worse ways for a financial institution to become part of a place. There are few more human ones.