Barb Heinlein — Founder & CEO, Wig Circle LLC

Driven by both experience and empathy, Barb Heinlein founded Wig Circle to bring trust, connection, and confidence to the wig-wearing community — one story, one conversation, and one shared experience at a time.

Career Highlights

Barb Heinlein is an accomplished IT Executive, FinTech Leader, and retired U.S. Air Force Colonel with more than 25 years of success leading enterprise-scale technology and digital modernization initiatives across federal, financial, and commercial sectors.

Her distinguished career reflects a rare combination of technical depth, executive leadership, innovation, and mentorship-driven purpose — consistently uniting complex systems, high-stakes missions, and human purpose through technology.

U.S. Air Force Colonel (Retired): Commanded one of the Air Force’s few engineering & programming squadrons and led development of the Air National Guard’s first automated force management system. Later served at the Pentagonas Deputy Chief Technology Officer and Senior Military Assistant to the DoD CIO, guiding enterprise cybersecurity and network modernization strategies across the Department of Defense. Among the most meaningful parts of her career was mentoring and developing the next generation of leaders — providing opportunities to deserving Airmen and officers, and seeing them advance with confidence and excellence.
Federal Leadership at CMS: Directed development and modernization of national enterprise-level healthcare IT systems at the Centers for Medicare & Medicaid Services (CMS), supporting PQRS (Physician Quality Reporting System) and the congressionally mandated System of Record (SOR) for End Stage Renal Disease (ESRD) data management systems — including CROWNWeb, REMIS, and the ESRD Quality Incentive Program (ESRD QIP). She was equally committed to mentoring her staff and cultivating strong, mission-driven teams that delivered lasting improvements to public health technology and data integrity.
Entrepreneur & Educator: Founded Raving Software, a digital marketing and web development firm, and later taught computer science as an Adjunct Professor at Anne Arundel Community College, mentoring students in object-oriented programming and content management systems.
Corporate Executive: Served as Vice President, Application Support at JPMorgan Chase, where she was the primary technology contact for several of the firm’s largest enterprise credit card processing clients — resolving high-impact issues, driving platform improvements, and building trusted relationships across a complex global payments environment.

Program Leadership & Impact

Throughout her career, Barb has led and directed technology and modernization programs ranging from multi-million-dollar projects to multi-billion-dollar portfolios, overseeing the modernization of critical healthcare, defense, and information systems. She has guided high-value national IT initiatives — ensuring disciplined execution, strong governance, and transparent delivery. Recognized for her strategic leadership, integrity, and mission focus, Barb consistently advances programs that strengthen trust, reliability, and public confidence in technology and government systems.

The Journey to Wig Circle

After decades of leading large-scale technology programs and mentoring teams, Barb felt called to build something more personal — a project rooted in empathy as much as innovation, and driven by a desire to make a tangible difference in people’s everyday lives. She often joked that her fine, thin hair was “the bane of my existence,” a lighthearted phrase that reflected years of frustration and trial.

In that search for answers, Barb discovered Denise Sheets, a wig influencer whose YouTube tutorials introduced countless newcomers to the world of wigs. Denise’s openness, education, and supportive community immediately resonated with Barb. When Barb attended Denise’s first Wig Conference, she was inspired — not only by the artistry and confidence of those in attendance, but by the genuine sense of belonging they shared.

That experience sparked an idea: to combine her lifelong skills in technology and leadership with a mission of compassion and connection. What began as a personal search for confidence and community evolved into Wig Circle — a platform designed to blend technical excellence with genuine care, giving others that same sense of trust, empowerment, and belonging she discovered along the way.

The Vision Behind
Wig Circle

Building on that experience, Barb founded Wig Circle — a digital community rooted in compassion, trust, and empowerment.

Wig Circle brings together wig wearers and supporters in a safe, inclusive environment where members can connect, learn, and earn recognition for their helpful contributions. The platform also features a peer-to-peer Marketplace for verified members to buy, sell, or exchange quality wigs and accessories within a trusted network.

By merging the structure of a social network with the integrity of a vetted marketplace, Wig Circle reflects Barb’s lifelong philosophy: technology is most powerful when it strengthens human connection.

Guided by Purpose

Across every phase of her career — from commanding Air Force software engineering teams to shaping national healthcare data systems and advancing FinTech platforms — Barb has used technology to serve people, foster trust, and create opportunities for others to succeed.

Through Wig Circle, she continues that mission — building digital spaces that empower, uplift, and unite those navigating their own journeys with courage and authenticity.