Gregory Schipilliti, the International Director of DailyPay, Inc. He is a prominent figure in the rapidly evolving financial technology sector. His journey is a compelling tale of resilience, reinvigoration, and relentless purpose. From humble beginnings to guiding global growth at one of the most disruptive firms in earned wage access, his career reflects a unique blend of operational acumen and empathetic leadership.
Raised by a deep appreciation for hard work and responsibility, his early professional years were not only shaped by ambition, but a deep-seated belief in financial empowerment. It’s this very belief that later found a perfect alignment with DailyPay’s mission—to build a financial system that works for everyone. His path to leadership is a well measured climb in international landscapes, building expertise in financial operations, scaling business units, and bridging cross-cultural teams with the intention of putting out a single unifying message: dignity in work should come with dignity in pay.
After joining DailyPay, Schipilliti has been instrumental in transforming the company’s footprint beyond U.S. borders, bringing their innovative earned wage access model to new markets. However, beyond the metrics and milestones, he remains a leader who listens first. Colleagues describe him as someone who leads from the front—decisive, but grounded; strategic, but personal. Whether mentoring rising leaders or negotiating with international partners, his aim is always the same: purpose over prestige.
At a time when the global workforce is demanding flexibility, transparency, and trust, Schipilliti’s leadership signals more than just expansion—it signals a recognition of what leadership in fintech should be like. Not merely about growth for growth’s sake, his work underscores the value of impact-driven innovation. As DailyPay looks to the future, it does so with a steady hand at the helm —one that measures success not just by quarterly returns, but by the lives of the individuals.
Business with a Purpose Beyond Profit
The roots of Mr. Schipilliti’s professional journey stretch far deeper than a résumé. They trace back to the lessons taught at the family table, where his parents encouraged curiosity and perseverance. These values crystallized into action through personal milestones and pivotal life events. “My wife’s unwavering belief in me pushed me to strive for deeper meaning in my career, prompting reflection on what truly matters. Yet, it was the tragic loss of my mother that became a turning point—prompting a re-evaluation of purpose and a redirection of energy.” he says.
That reflection led him to DailyPay, a company whose mission to reimagine financial wellness aligned seamlessly with his personal values. Here was not just a job, but a purpose—to help individuals regain control of their earnings and foster stability within families. This alignment between vocation and values offered a kind of fulfillment that transcends traditional corporate metrics. DailyPay became more than a workplace; it became a platform to honor his mother’s memory and contribute meaningfully to a more equitable financial ecosystem.
His innate curiosity—once a source of childhood wonder—now fuels innovation and strategic thinking in business. The foundational discipline from youth, magnified by personal trials and loving support, found its ultimate expression in a role where passion and purpose met. Gregory’s journey into the professional sphere wasn’t motivated by titles or applause but by a deep-seated desire to build something that matters—for families, for communities, and for future generations.
Navigating Dual Arenas: Family and Profession
Mr. Schipilliti is acutely aware of a truth many overlooks: time cannot be created. He often recalls the advice of a mentor who said life consists of three spheres—family, self, and profession—and that at any given moment, you can excel in two, but not all three. Gregory’s chosen hierarchy—family first, then self, then profession—grounds him in the decisions he makes, both big and small.
His awareness of limitations does not hinder him; it sharpens his focus. Recognizing he may never be the smartest person in the room, Gregory turns this into a strength by emphasizing team synergy, executional excellence, and informed decision-making. His leadership style is decisive, intentional, and rooted in strategic clarity. Whether it’s shaping go-to-market strategies, influencing product design, or driving operational precision, he approaches business with rigor and a data-first mindset.
Yet, the real balance emerges not from spreadsheets or leadership seminars but from the heartbeat of his home. His wife and three children center on him, offering clarity, motivation, and love. They remind him of his parents’ sacrifices and the lessons from his mother, especially the idea that trauma belongs in the past, and that one’s attitude shapes the future. The moments of peace—a sip of Tempranillo, a midday siesta, or shooting hoops with his kids—do not escape but affirmations that he’s living by design, not by default.
Success, to him, is a peace of mind earned through disciplined effort, moral clarity, and the joy of presence. And sometimes, it’s simply found in shared laughter over dinner or an evening game with his children.
An Unquenchable Curiosity for Enterprise
To understand Gregory’s appetite for business is to witness a mind that never fully turns off. “Business, to me, is not merely a profession, it’s a canvas. A canvas where problems transform into opportunities, where ideas are painted with action, and where purpose underpins every stroke of decision.” he quotes.
What energizes him is not the pursuit of profit, but the pursuit of meaningful outcomes. Business is his means to help solve problems, design legacy, and enable progress that will outlast his generation. He views it as a vessel to uplift, to connect, and to build a better world for those yet to come.
His curiosity extends across the full spectrum of business: supply chains, compliance, capital markets, engineering, distribution, and more. Every function holds lessons and leverages innovation. And while he does not claim omniscience, he approaches each challenge with humility and hunger. As his mother used to say, wisdom lies in knowing you are not the smartest in the room. This ethos keeps him grounded and eager to learn.
Whether it’s architecting a go-to-market strategy, or understanding regulatory landscapes, he embraces each layer of complexity as a new chapter in the story of impact. Staying humble, staying hungry, and staying grateful—these are not slogans for Gregory, but guiding principles.
Purpose Behind the Passion
For Mr. Gregory, the true fuel of his journey isn’t found in corner offices or executive accolades. It lies in the warmth of his home, the wisdom of his parents, the laughter of his children, and the unwavering partnership of his wife. His passion begins and ends with family.
Gregory describes himself as a simple man who finds joy in company, conversation, and life’s quiet pleasures. His signature response to “How are you?” is always a variation of “happy and you?” a reflection of his mother’s enduring lesson that how we make people feel creates ripples across time.
From childhood dreams of basketball stardom to boardroom strategies, have nurtured his path made it defined not by what he lost, but by what he’s chosen to honor. He holds firm to the belief that hard work, kindness, and a touch of wine now and then are keys to enduring joy. And when the world slows—sports silenced, children asleep—he finds comfort in that moment of reverie, a soft echo of assurance that everything will be okay.
Strengths That Build, Weaknesses That Teach
Gregory’s primary strength lies in his self-awareness. “Knowing I will never be the smartest person in the room, I lean into strategy, execution, and team building. My humility fuels a relentless pursuit of excellence which creates high-performing teams by empowering them with clarity, trust, and opportunity.”
He excels in communication, complexity management, and data-driven thinking. But like any passionate leader, he faces the eternal challenge—there aren’t enough hours in the day. Balancing fatherhood, leadership, and personal well-being is a daily endeavor. He’s learned to be more efficient, more focused, and more forgiving—especially toward himself.
For those watching and learning, Gregory offers a powerful lesson: “Your weaknesses are not Your end, they’re your edge. They teach you a lot, they are humble, and they evolve with time.”
Defining Achievements Through Gratitude
When asked about awards or accolades, Gregory offers a smile. “For me, recognition isn’t found in plaques or podiums, it’s reflected in the life I live.” He married his best friend and hero his wife Gema. He is a father who deeply loves his children. He honors the legacy of parents who sacrificed for his growth and maintains lifelong friendships that anchor his spirit.
While his résumé may be decorated with roles at iconic brands and pioneering projects, he is most proud of having built a life he’s deeply grateful for. Those who know him know that every word he speaks is rooted in truth and sincerity. That, in his eyes, is the ultimate accolade.
Leadership as Service and Stewardship
Mr. Gregory believes, “Leadership is not a crown but a responsibility. It is a privilege earned through trust, effort, and clarity of purpose. I was taught early that leadership is about service and not grandeur.” He approaches it with humility, believing the best leaders learn tirelessly, listen attentively, and act courageously.
To those aspiring to lead, he offers this counsel: Cultivate endless curiosity. Learn deeply and widely. Fail bravely and recover gracefully. Listen before speaking. Act with empathy and urgency. Focus on impact over image.
Leadership, as he defines it, is a long road paved with self-reflection, resilience, and resolve. And at the end of that road lies a truth Gregory Schipilliti lives by: If you work hard, stay humble, and love deeply—everything will be more than okay.
