Sabrina Bailey

How long have you worked in the financial services and enterprise technology sectors? What drew you to them?

I have spent 26 years in financial services and enterprise technology and my path into this work began with a single conversation that changed everything. During an internship my senior year of college, a mentor helped me see that the work we do extends far beyond our direct client. Every decision, every action, carries a ripple effect, touching the lives of individuals in deeply meaningful ways. From someone carefully placing their hard-earned savings into a retirement plan, to the beneficiaries of philanthropic organizations, the stakes are profoundly human.

That perspective lit something in me. It transformed what could have felt like a career in numbers into something deeply human; a personal mission to help people achieve financial security. That sense of purpose has guided every step of my career since.

What does it mean to you to be a female in a leadership role?

Being a female leader means choosing the harder, more purposeful path even when the easier road is tempting and the weight of resistance is real.

Early in my career, I sat at tables where I was not fully welcomed. I was talked over, talked around, and occasionally told my place was somewhere else entirely. Each of those moments presented a choice: react from a place of wounded pride or respond from a place of character. I learned quickly that the future unlocked by letting pride go is far greater than any momentary satisfaction of being right. These experiences didn’t harden me, they strengthened me.

They fueled a conviction I carry into this role every day: that the most powerful thing any leader can do is believe in others before they fully believe in themselves; helping them see doors they didn’t know existed and then opening those doors so they can walk through and become who they were designed to be.

True leadership is never about title. It is earned in the small, quiet moments; in how you show up for people, in the trust you build one honest interaction at a time, and in the courage to listen when every instinct tells you to speak. Influence, not authority, is the soul of leadership.

What’s the most meaningful experience you’ve had working with a nonprofit or philanthropic family?

Narrowing it down to a single experience feels impossible as each one has shaped me in its own profound way.

What I can say is this: the most meaningful lesson I have carried out of the philanthropic space, working alongside clients and communities around the globe, is that true transformation is never built overnight. Sustainable impact is rooted in investing in people; offering a hand up rather than a handout. And while that distinction sounds straightforward, living it out requires years, often decades, of patient, purposeful commitment.

The joy that comes from witnessing that level of transformation is never immediate. But it is deep. And it is lasting. That depth is what draws me back, every time, and reminds me why this work matters.

What advice would you give to the next generation of women working in philanthropy, financial services or enterprise technology?

My advice is simple: choose an attitude of gratitude. Gratitude is not naivety. It is the foundation from which the most resilient, impactful leaders build their lives and careers.

Our attitude is the one thing entirely within our control. We cannot choose what happens to us or the world around us, but we can choose how we show up in response to it. That choice, made intentionally every day, is more powerful than any title or opportunity that will come your way.

Some days that choice is harder than others. When circumstances are difficult, our natural tendency is to look around and focus on what others have that we don’t. But if we purposefully pause and shift our gaze, we find something different. We find that in most cases there are far more people we can reach back and lift up than there are people standing above us. That perspective resets everything, providing the foundation for gratefulness.

How can women support other women in their organizations?

First and foremost, remember this: we are not each other’s competition. We are each other’s greatest resource and strength. When we choose to show up for one another in small, purposeful ways, we don’t just change individual lives; we change the culture around us.

There are three simple but powerful steps you can take today to support another woman in your organization:

1. Believe in her before she fully believes in herself. Some of the most transformative moments in my career came when someone saw potential in me that I couldn’t yet see in myself. Be that person for someone else.
2. Speak her name in rooms of opportunity when she is not there to speak for herself. Advocacy doesn’t always require a grand gesture. Sometimes the most powerful thing you can do is simply make sure she is seen.
3. Have the courage to offer honest feedback, wrapped in grace. Celebrate her wins and hold up a mirror to the places where growth is still possible. That rare combination of truth and care is one of the greatest gifts one leader can give another.

None of this is complicated. But practiced consistently, it is transformative.

What is your favorite book, podcast or product from women creators?

Because I am an avid reader and there is a long list of powerful books written by women, below are my top two current favorite business reads:

• Likeable Badass: How Women Get the Success they Deserve by Alison Fragale
• Quiet: The Power of Introverts in a World that Can’t Stop Talking by Susan Cain

Have you had any female role models that have inspired you throughout your career?

I have too many female role models to name. They span the lineage of women in my own family – butchers, steel welders, administrators – to entrepreneurial women serving the poorest in their communities to remarkable women within our own industry. Each one navigated a world that was not designed for her and built something meaningful within it anyway. They taught me that there is no single mold for strength.

What truly unites them is this: none of them sought recognition. None of them waited for permission. They led with character, served with consistency, and left every person and place better than they found it.

We would like to welcome and congratulate Sabrina on her new role and thank her for sharing her story with us! You can check out more inspiring interviews with other women leaders here.

Want to learn more about the ways we support charitable giving?

We have a full range of tech-enabled charitable giving solutions to serve your unique needs. To learn more, schedule a call with us or reach us at 800-839-0054. Together, let’s #begiving.