CPA, SME, and Purpose: Exploring the Power of Multifaceted Professional Identity

What happens when sharp accounting meets sun-soaked strategy? In this episode of Professional Quotient: Conversations that Build Equity, host Jason Winningham welcomes Olivia Barr, Senior Product Manager at CBRE, for a dynamic conversation that explores career pivots, process excellence, people leadership, and the power of community. Olivia brings the full spectrum of professional equity and a multifaceted professional identity that spans high-impact roles in accounting, product management, and immersive travel experiences—from her work as a CPA and product leader to her passion as a certified Caribbean travel concierge.

We talk about what it means to lead with intention, to ask the tough questions, and to create systems that actually work—for businesses, for teams, and for travelers seeking meaning beyond the itinerary. Olivia shares her early-morning routines, the story behind her career pivots, and how a disappointing trip became the spark for a business built on advocacy and care.

Key Talking Points:

• Challenging the Status Quo: Olivia shares how her CPA background has honed her ability to see gaps in processes—and how she uses this insight to lead transformative change within her organization.

• Building with Purpose: Whether leading product development at CBRE or planning immersive travel experiences through her business Caribbean Island Festivals, Olivia emphasizes values-driven work and mentorship as keys to sustained impact across her multifaceted professional identity.

• From Fear to Leadership: Olivia opens up about overcoming her fear of public speaking, revealing how involvement in professional groups helped her grow into a confident, vocal leader.

• You’ll also hear how a speech impediment became a defining strength—and why real leadership always starts with empathy and preparation.

Whether you’re here for business insight or island inspiration, this episode delivers both.

Olivia Barr is a powerhouse of versatility. A CPA by training and Senior Product Manager at global real estate firm CBRE, Olivia brings a data-driven, people-focused approach to everything she touches. She is also a certified Zumba instructor, founder of Caribbean Island Festivals, and a travel SME with certifications from Caribbean tourism boards. Olivia holds a degree in Management Information Systems and Accounting, and credits her pivot into accounting to the support of the National Association of Black Accountants. Known for her go-getter mindset, Olivia continues to inspire others with her leadership, mentorship, and passion for professional equity.