Founder & CEO, Retail Women in Tech | Author of Choose, Don’t Chase, Your Career | Bridging the Gap Between People, Pathways, and Purpose in Retail Tech
For Shannon Flanagan, retail has never been just about the transaction; it has always been about the pulse of the person behind the counter and the vision of the leader in the boardroom. She often describes her career with a visceral honesty: “In short, I bleed retail.” But for Flanagan, this deep-rooted industry expertise is merely the vessel for a much larger mission. Her true “why” is found in the ripple effect—the belief that when an individual finds fulfillment and dignity in their work, that energy radiates outward to transform families, communities, and eventually, the world.
As a self-described “Humanist,” Flanagan has spent over three decades navigating the complex intersections of commerce and soul. From the early days of working on the store floor to spearheading strategic initiatives for global giants like Gap Inc., Macy’s, and Accenture, her trajectory has been defined by a refusal to separate professional excellence from human connection. Today, as the Founder and CEO of Retail Women in Tech (RWIT) and a soon-to-be-published author, she is rewriting the rules of engagement for an entire industry.
The Alchemy of Grit and Grace
The seeds of Flanagan’s leadership were sown at the age of 18. While many executives enter the industry through the detached lens of data and analytics, Flanagan began where the heart of retail beats: in the stores. Her early years in merchandising and store operations provided a ground-level education in human behavior, resilience, and the intricate mechanics of consumer needs.
This period instilled in her a “GSD” (Get Stuff Done) mindset that remains her hallmark. She learned early on that success in retail requires an equal measure of grit and grace. Her education at Saint Louis University, where she studied History, further refined her ability to see the broader context of societal shifts—a skill that would later allow her to anticipate the technological and cultural disruptions facing the modern workforce. This blend of historical perspective and frontline experience created a leader who values people as much as she values the bottom line.
The Art of the Genuine Partnership
As Flanagan moved into the upper echelons of corporate leadership, her reputation became synonymous with “partnership over sales.” During her tenure at organizations like Slalom, Talkdesk, and Writer, she didn’t just manage accounts; she built ecosystems. Joshua Mahoney, a former client and Chief Product Officer, recalls her unique approach: “Working with Shannon was much more partnership than her ‘selling’ a service regardless of what we needed. The fact that she has great understanding of retail really helped as well.”
Her rise was marked by a relentless curiosity about how technology could serve humanity rather than replace it. She became a sought-after voice in AI adoption and digital transformation, not because she was enamored with the software, but because she saw its potential to unlock human capacity. This era of her career was a masterclass in “verticalization”—the art of connecting the dots between high-level strategy and the practical realities of the people executing it.
Colleagues like Rick Johnson, RVP of Sales, noted her selfless approach to leadership: “She’s an executive always willing to mentor others and help them achieve results. She’s selfless with her time and definitely willing to dig in and get her hands dirty.” For Flanagan, growth was never about reaching the top alone; it was about building a ladder for everyone else.
Driving Parity and Strengthening Mobility
In early 2024, Flanagan transitioned from helping companies scale to helping humans thrive. She founded Retail Women in Tech (RWIT), a global movement that recently achieved 501(c)(3) nonprofit status. RWIT was born from a realization that traditional networking was failing women. Flanagan envisioned something different: a community that wasn’t hidden behind a paywall, but one that actively dismantled the barriers between people, pathways, and purpose.
“RWIT exists because the current models for advancing women, while well-intentioned, haven’t delivered enough momentum,” Flanagan asserts. Under her leadership, the organization has become a sanctuary for “whole humans,” focusing on quality connections over transactional business card swaps.
Her impact extends beyond career mobility. As a staunch advocate for mental health, Flanagan serves on the Global Mental Health Taskforce, working to end the stigma surrounding mental wellness in the workplace. Her philosophy is simple yet radical: every mind deserves care, and that care must be accessible. By integrating mental health into the professional narrative, she is humanizing the executive experience in a way few others dare to do.
A New Narrative for the Modern Career
As Flanagan looks toward the horizon, her focus is squarely on helping others navigate their own transitions. Her upcoming book, Choose, Don’t Chase, Your Career, challenges the outdated narratives of the “hustle culture.” It serves as a manifesto for women to move through their professional lives with clarity, courage, and intention.
Flanagan is no longer just a retail expert; she is a life transition specialist. Her vision is to create a world where individuals are seen for who they are, not just what they do. Whether through her writing, her speaking engagements, or her leadership at RWIT, she continues to act as a catalyst for change.
She remains the ultimate connector—a leader who leads with warmth and wisdom, ensuring that the people she touches have each other’s backs. In the world of Shannon Flanagan, the goal isn’t just to reach the destination; it’s to become who we are meant to be along the way.
Editorial Note
Shannon Flanagan’s journey reminds us that leadership is not a title, but a commitment to the “ripple effect.” By prioritizing human fulfillment and mental well-being, she has provided a blueprint for the next generation of leaders. How are you choosing—not chasing—your path today?
