Schilling, with scissors, at MESBA’s ceremony marking the end of road construction. Signage, like this gateway for Cottage Grove Road, is now in a style consistent along Monona Drive.
Three years ago, when Kristie Schilling became executive director of what was then known as the Monona Chamber of Commerce, the organization was struggling. Membership was down, the financial situation, dire. “We were on nonprofit death’s door,” Schilling says. “It needed an overhaul, a rebrand, some energy poured in.”
But Schilling was up for the challenge. Shortly after taking the helm, she unveiled a new name: The Monona East Side Business Alliance. She also shifted the group’s approach to focus on building connections between businesses in Madison’s Atwood neighborhood and on Monona Drive. “There really was not a business association serving the east side,” Schilling says. “The way our communities are intertwined, it just made sense.”
In Schilling’s first year, MESBA added 64 new members. She launched new networking initiatives, organizing kayak outings and beer and cheese tastings instead of the more typical happy hours and golf outings. She also put together a successful Restaurant Month promotion and a curatorial service connecting local artists with businesses interested in displaying their work. MESBA member Amber Swenor, who owns Strategic Partners Marketing and Amberdella Consulting, says Schilling’s innovation and leadership has transformed the organization.
“From the feeling I get, things needed to change or the organization really would have struggled,” Swenor says. “Now we’re flourishing because of the innovative ideas that have been put forth — they’re mostly Kristie’s ideas.”
Schilling grew up “very poor” on Drummond Island, a remote community in the Upper Peninsula of Michigan. Her mother dropped out of school in 10th grade when she became pregnant with Schilling’s older sister and her father left the family when Schilling was just a year old.
“My mom worked around the clock to support us,” says Schilling, now 46. “I raised myself from age 4.”
On the island, Schilling faced discrimination for her Native American heritage and her past was shaped by tragedy — first came the death of her best friend, who died at age 8 from a heart defect. “It gave me a sense of the fragility of life at an early age,” she says.
A few years later, Schilling’s sister died in a fire that was intentionally set by a foster child her family had taken in. “She had a troubled past,” Schilling says of her foster sister, who filled the the bathtub of the family’s trailer home with lamp oil and set it ablaze. Schilling and her mother escaped, but they never told anyone in the community the truth about what happened, fearing vigilante justice.
Schilling’s mother was “beyond devastated” after the fire and moved to Hawaii to become a missionary. Left alone at age 17, Schilling relocated to Door County, where she had family and could find work in the service industry. She struggled to get by, becoming homeless at age 22. She slept on the steps of the Sturgeon Bay Library and in the car that her mother had left behind. She dreamed of going to college, but believed it was unattainable.
“When you grow up poor, teachers never ask you about college,” Schilling says. “I wanted it so bad but had no hope for it.”
But a friend she met while working in restaurants encouraged her to apply, helping her navigate the admissions process and apply for financial assistance. She was accepted at UW-Madison, where she studied geography and fine art. She waited tables at restaurants on Madison’s east side while in school. It was her first introduction to the area she now serves. After college, Schilling worked as a cartographer, making digital maps for National Geographic. She later started her own graphic design firm and worked for the Fitchburg Chamber and Visitors Bureau.
For Schilling, life in Monona is idyllic. She describes the city as having a “summer camp” feeling, with residents frequently hauling kayaks to the beach and kids often running around in swimsuits. “It has a small-town vibe and a close-knit feeling, with the amenities of Madison right across the street. The amenities are outstanding — that’s why people can’t buy homes here,” she says, referencing the hot real estate market.
Since taking over the reins of MESBA, Schilling has grown the organization to 350 members and has several new initiatives in the works, including a program for local businesses to mentor at-risk youth. She hopes to help facilitate more business growth along Monona Drive and may one day represent the area as an elected official.
A self-described “political junkie,” Schilling signed up with Emerge Wisconsin, an organization that trains Democratic women to run for office. She was moved to get involved after the 2016 election and hopes to help restore a sense of authenticity to politics.
“So many people think you have to be fake to be in politics, but I’m as real as it gets,” she says. “Do I have a spotless history? No. But second chances are awesome.”
Editor's note: The story has been updated to reflect the correct spelling of Schilling's surname.
