She Built the Solution She Needed. Now She Wants to Share It with the World.
The story of Jessie Shipman and her company, Fluincy, defies the classic narrative of entrepreneurship. For Jessie, business wasn't a foreseeable path mapped out by family traditions or childhood dreams. Instead, it was an unintended detour sparked by frustration and a profound gap in business strategy that begged for a solution.
"I actually never thought I would be an entrepreneur," Jessie reflects. Growing up in a home where both parents embraced the stability of W2 jobs—her father in the Air Force and her mother rising the ranks of project management—she naturally assumed she'd climb the corporate ladder. Fast forward to several pivotal career moments, and Jessie found herself gravitating toward roles that intertwined her myriad passions—technology, education, and partnerships.
Jessie's journey into tech started unexpectedly. After a series of moves and career shifts, she found herself deeply involved in IT and later landed a coveted role at Apple as a K12 systems engineer. It was here she discovered her calling in partner enablement—a role that seamlessly blended her love for teaching and problem-solving with her technical expertise. “It was a total dream and I loved every minute of it,” she explains.
But perfect fits are sometimes flawed. Jessie hit a wall when the traditional ways of partner enablement began to feel outdated and ineffective. “The real goal of teaching is the behavior change that accompanies new information,” she says, emphasizing the discrepancy between what partner enablement was and what it could be. When she realized the methods of engaging and educating partners didn’t translate into revenue and long-lasting partnerships, she saw an opportunity.
Despite the comfort she found in her role, Jessie was compelled to act. Her quest for a solution turned into an entrepreneurial endeavor when she realized the tools she needed didn't exist. And so began Fluincy—a company born out of necessity. "Someone should Google how to start a software company," she thought, kickstarting her initiation into the intricate world of startups.
The path wasn’t sugar-coated. Jessie spent nine months caught in the whirlwind of chasing venture capital based on an idea alone, only to realize that the market, especially for female founders, wasn't receptive. But adversity planted a seed of resilience. “I might as well just build a business and let them come to me,” she decided, choosing to bootstrap her way forward.
Yet, bootstrapping as a solo founder came with its own set of challenges. Jessie candidly shares, “It’s really hard and it’s not great.” Building a founder brand, marketing, and trying to educate the market one interaction at a time consumes her efforts. But despite the grind, there’s unshakeable conviction in her mission—she’s seen the problem, lived it, and refuses to let it go unsolved.
Conferences and community have become Jessie's fuel. At gatherings like SAS talk and through connections such as Wednesday Women, Jessie gains validation and the drive to “keep talking” about the necessity for effective partner enablement. “The reality is I need to keep repeating myself,” she acknowledges. It's a dedication that echoes the fundamental lessons she learned as a teacher—change takes time, and sometimes incessant persistence.
While uncertainty looms over the question “Is this a viable business?”, Jessie's vision remains firm. By blending her deep knowledge in partnerships with a relentless commitment to resolve overlooked business gaps, she’s not just climbing a mountain—she's redefining the path for others to follow.
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