Sherpa melds family history and modern practices in its full-building remodel of the former auto dealership in Midtown Alley. There, it produces software that helps senior living professionals serve as “emotional Sherpas,” guiding older adults through the difficult decision to enter a senior living community.
Sherpa’s office-front is a study in extremes: glass and steel are warmed by woods and carpets; the space brims with vintage photos of the founders’ friends and family alongside trendy decorative finds and custom-built furniture creations.
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Where an old elevator shaft once ascended, a brainstorming room now stands, bedecked in textiles and covered in whiteboards; on the second floor, the same shaft has been converted into a mini-bar next to an outdoor patio.
“We love the old and new, the high tech and the mechanism of the old elevator,” says Alex Fisher, who co-founded Sherpa with her partner, David Smith.
The entry greets visitors with two-story, floor-to-ceiling windows, a stunning holdover from the space’s history as a car showroom. Square, custom-made cubicles—“pods”—line the windows inside, printed with a dash of orange and inspirational words.
Further inside, a long wall features more grayscale images: a group of smiling senior citizens, bigger than life-size. “That’s David’s mom,” says Fisher, pointing to a woman in the front. Another is Gladys, age 99; a former pilot who passed away at 97; a former mayor of Creve Coeur; the mother of Sherpa’s last COO. Each comes with a name, an age, a story.
“Our product promotes empathy and connection; we wanted our building to do the same,” explains Fisher. The design sprang from a collaboration with development consultant Jassen Johnson, who acted as everything from real estate broker to architect and designer. He’s a veteran developer of the neighborhood; Sherpa is his 48th project in the Midtown Alley neighborhood. Most importantly for Fisher, Johnson “painted the picture” that brought those themes together.

And the building is more than one step up from the basement of the Gatesworth senior living facility, where Sherpa’s offices first opened in 2014, after a decade’s-long germination. Sherpa moved into the new space in October 2016, after a year-long renovation.
Accents are “inspired by Alex’s [Argentine] heritage,” says Johnson: throughout the office, cow-print flooring recalls her days on a ranch. “It makes me feel at home,” Fisher adds.
Fisher also commissioned a mammoth sculptural table that sits in the raised, glass-walled conference room—a nuance that Fisher’s woodworking father would have loved. Petrified wood legs hold a thick, whorled trunk section to create the “Elephant Table,” as it’s called. “The history of life is basically in this table,” says Johnson. To Fisher, it’s a focal point for doing work and making decisions, and named after her favorite animal, known for its wisdom, to boot. “Without getting so poetic—it’s pretty poetic,” Fisher reflects.
“All of those things visually change the cold makeup of glass and steel,” adds Johnson.
An artist herself, Fisher selected some of her favorite figurative works to decorate the walls. A calming yoga and meditation room was designed in teal and orange to match one of Fisher’s artworks. “I hung them all while she was in a meeting so she couldn’t argue with me,” says Johnson.

The decorative features reflect both a philosophical core and a functional purpose. With a spin and a roll, the pods can join in clusters; steps become connected walkways and individual offices turn into collaborative units. Another spin and the sunlight is blocked from the front windows; open the standing desks to face a partner or two. “It’s designed around collaboration,” says Johnson.
The office environment encourages work-life balance. One nook was transformed into an orange rock wall. Hula hoops are a common sight around the office and an in-progress chess game sits on a table in front of the downstairs patio. Just a few weeks ago, the employees tested a group yoga program.
“Where you work should matter. It’s a third of your life. Why not have fun?” asks Alex.
Jassen says that the only design flaw is that the employees like the office a little too much.
“We can’t get them to leave the building to try the local restaurants often enough,” he says.