Why Authentic FinTech Leadership Starts with Listening

FinTech Leadership and Inclusion

On this episode of FinTech’s DEI Discussions, hosted by Nadia, we dive deep into the inspiring story of Gemma Ros, Chief Technology Officer at The Zebra. Her career journey—from an immigrant childhood to the leadership team of a prominent FinTech business—is one of resilience, curiosity, and intentional inclusion. In this insightful conversation, Gemma and Nadia explore what it truly means to walk the talk when it comes to inclusive leadership, career acceleration in FinTech, and building meaningful workplace cultures.

This episode offers invaluable insights for anyone interested in FinTech recruitment, leadership development, and cultivating diverse and equitable work environments. As a FinTech recruitment business, Harrington Starr is proud to highlight conversations like these, which offer essential guidance for building and supporting the talent that shapes our industry.

From Self-Taught Technologist to CTO in FinTech

Gemma Ros begins her story with humility and humour, revealing that her path to the C-suite wasn’t linear. Born in Spain, she moved to South Florida at the age of nine. Like many children in immigrant households, she faced strong expectations to pursue a traditional career—her parents hoped she would become a doctor. But Gemma was always drawn to technology. Her father was an early adopter of gadgets, yet often didn’t know how to use them, which made Gemma the go-to person in the household for tech support.

Her first job was not in tech—it was as an executive assistant to a fund manager in Boston. At the time, she hadn’t considered software development a viable career path. Despite being self-taught in programming and building web applications for fun, it wasn’t until she saw analysts doing manual work in Excel that she offered to streamline processes using simple scripting. This small but impactful decision became the catalyst for her transition into tech. Encouraged by the impact she was making, Gemma returned to school for her Master’s and landed her first software developer role at Lehman Brothers on Wall Street—right at the onset of the financial crisis.

Seven years in investment banking and another ten in various financial services roles later, she joined The Zebra, first as Head of Engineering and, more recently, as CTO. Her experience showcases the kind of determination and adaptability that defines many success stories in FinTech.

What The Zebra Brings to the FinTech Landscape

Gemma explains that The Zebra is an insurance comparison platform dedicated to making the insurance shopping process transparent, fast, and human-centred. Partnering with over 100 insurance carriers, the platform allows users to compare quotes across auto, home, renters, and even pet insurance.

But The Zebra does more than compare quotes. It decodes them—helping consumers understand what they’re buying, the trade-offs involved, and which coverage suits their lifestyle and not just their wallets. This people-first approach is mirrored in the company’s product strategy and culture. For Gemma, the intersection of technology, data science, and human empathy lies at the heart of The Zebra’s mission.

FinTech Culture and DEI in Practice

At The Zebra, inclusive values are not just spoken—they are embedded into the organisational fabric. One of the standout features of this conversation was Gemma’s description of how The Zebra has built a culture that celebrates individuality while creating intentional connection. Employee Resource Groups (ERGs) play a pivotal role in that.

The company currently has five active ERGs, including:

• Shera, for women and allies
• Dazzle, for the LGBTQIA+ community (a name inspired by the fact that a group of zebras is called a “dazzle”)
• Stars and Stripes, supporting active and retired military members and their families

These groups go beyond token gestures. They host events, shape internal policy discussions, and create space for underrepresented voices. What makes them even more impactful, Gemma notes, is the active engagement from executive leadership, who partner with ERGs to implement change, not just support from the sidelines.

One standout initiative Gemma shared is a biweekly pairing program where employees are randomly matched for 30-minute conversations with colleagues across the business. This simple but effective approach to human connection fosters empathy, collaboration, and a culture of openness. It’s a model any FinTech firm looking to improve its culture could adopt instantly.

Building Community Through Leadership Networks

Gemma is also a founding member of the Miami chapter of Chief, a private network designed for senior women leaders, including VPs, C-suite executives, and founders. The goal of the community is to address the isolation often felt by women at the top and provide a peer-driven support system for continued leadership development.

In Chief, Gemma belongs to a “core group”—a small circle of women at similar career stages who act as personal advisory boards for one another. This group provides a safe space for candid conversation, decision-making support, and mutual accountability. It’s been a vital part of Gemma’s leadership evolution, helping her navigate challenges with confidence and clarity.

The Impact of an Immigrant Background on FinTech Leadership

A recurring theme throughout the episode is how Gemma’s background as an immigrant has shaped her perspective as a leader. Moving to a new country, learning a new culture and language, and watching her parents rebuild their lives instilled a profound sense of drive and gratitude. It taught her to value every opportunity and to work hard not just for personal success, but in honour of her family’s sacrifices.

But this background also came with challenges, including impostor syndrome. Even as she advanced in her career, Gemma admits to sometimes questioning whether she belonged in the room. For many professionals from underrepresented backgrounds, this internal conflict is all too familiar. Her response has been to reframe difference as strength—a perspective that has enabled her to approach problem-solving and leadership through unique lenses.

Gemma’s leadership style is rooted in empathy, authenticity, and an understanding that people shouldn't have to conform to feel seen or valued. This philosophy informs her approach to team building, performance management, and culture creation—qualities that define modern, effective FinTech leadership.

Leading With Intention: Everyday Habits That Matter

When asked about how she continues to grow as a leader, Gemma spoke about the importance of daily practices and small, intentional actions. Active listening sits at the top of that list. In remote or hybrid FinTech environments, creating space for meaningful conversations is essential, not just for task management but for fostering connection and psychological safety.

Transparency also plays a major role. By sharing the reasoning behind decisions and the trade-offs involved, leaders build trust. Gemma believes that openness fosters authenticity, and authenticity creates the conditions for inclusive, innovative work.

Another powerful ritual she mentioned is “Little Wednesday”—a Slack channel where employees are encouraged to share small wins. From a child picking out their own outfit for school to finally finishing a long-neglected book, these moments are celebrated equally with big launches and project milestones. It reinforces the message that everyone’s contribution, no matter how small, is valuable and worth recognising.

Gemma’s leadership is about more than just driving performance; it’s about building environments where people feel safe, supported, and excited to do their best work. In the context of FinTech recruitment, this mindset is vital. At Harrington Starr, we know that the most successful placements are those where values and vision align—not just skills and experience.

Accelerating Careers in FinTech: Advice for Aspiring Leaders

As the episode draws to a close, Nadia asks Gemma what advice she would offer to professionals seeking to accelerate their careers in FinTech and beyond. Gemma is quick to clarify that there is no single path to success, but she offers three powerful pieces of advice drawn directly from her own journey.

First, stay relentlessly curious. Being the person who constantly asks “why?” is a strength, not a weakness. Those who move fastest in their careers are the ones looking beyond the task at hand and into the broader strategy, future challenges, and emerging opportunities.

Second, embrace discomfort. Gemma encourages people—especially women—not to wait until they feel 100% ready to take on a challenge. Growth happens when you step outside of your comfort zone. Saying yes before you're fully prepared builds confidence, resilience, and a powerful track record of courage and capability.

Third, build meaningful relationships. Don’t just network—build a circle of mentors, sponsors, and peers who will challenge and champion you. For underrepresented professionals in FinTech, these relationships can be critical to career growth. And as you rise, hold tight to your values. Gemma emphasises that leadership will always test your priorities, so knowing what you stand for ensures you lead with integrity.

Championing Inclusive FinTech Recruitment and Leadership

This episode of FinTech’s DEI Discussions is a testament to the kind of leadership the FinTech industry needs more of—intentional, inclusive, and human-centred. From her early days scripting automation solutions to her current role as CTO, Gemma Ros exemplifies what it means to lead with empathy and authenticity.

Her story is not only inspiring—it is instructive. For companies looking to attract top FinTech talent, the lessons in this episode are critical. Culture, inclusion, and leadership practices are no longer soft topics—they are competitive advantages. At Harrington Starr, we understand that to hire and retain the best talent in FinTech, you need more than a job spec. You need vision, values, and a commitment to DEI.

As we continue to help FinTech companies build high-performing teams, conversations like these remind us of the importance of walking the talk. Because at the end of the day, inclusive leadership isn't just good ethics—it’s smart business.