The Stratospheric CEOs of Financial Services

Georgie Dickins, Author, Managing Director & Co-Founder - Cajetan

Georgie Dickins on Leadership, Culture, and Resilience in FinTech

In the latest episode of FinTech Focus TV, Toby Babb sits down with Georgie Dickins, Author of Stratospheric CEOsand Managing Director & Co-Founder of Cajetan, to discuss the art of leadership and culture in the ever-evolving FinTech industry. Georgie’s remarkable career journey, her insights into leadership development, and her commitment to empowering the next generation of leaders make this an episode packed with inspiration and actionable advice.

From Financial Services to Transformative Leadership

Georgie began her career in financial services, spending 20 years specialising in electronic trading for interest rate swaps. Her journey in the corporate world gave her a deep understanding of leadership, organisational dynamics, and the intricacies of the financial sector. Seven years ago, she made the bold decision to step away from the corporate environment to Co-Founder of Cajetan, a boutique consultancy focused on leadership development and executive coaching.

At Cajetan, Georgie works with C-suite executives, visionary founders, and changemakers who are reshaping their industries. Her mission is to help leaders unlock their full potential and drive meaningful transformation. Her passion for leadership also led her to write Stratospheric CEOs, a book that distils the wisdom and lessons of some of the most successful leaders in FinTech. Through her writing, Georgie seeks to democratise access to the insights and strategies that have driven extraordinary success.

The Changing Face of Leadership in FinTech

A key theme of the episode is the evolution of leadership in FinTech. Historically, the sector has been dominated by male leaders, which is reflected in Stratospheric CEOs. The book focuses on male founders of multi-billion-pound FinTech businesses, highlighting their journeys, challenges, and achievements. However, Georgie acknowledges the need for greater diversity in leadership and is actively working to address this through her initiative, Women in Leadership Global.

This network was founded to equip women with the skills, behaviours, and mindsets needed to thrive in leadership roles. Georgie believes that representation is vital, as individuals are more likely to aspire to roles they can see themselves in. She is optimistic that the next wave of FinTech leadership will be more balanced, with greater visibility for women in senior roles. Her future projects include a follow-up book that will feature a more diverse range of leaders, reflecting the industry’s ongoing transformation.

At Harrington Starr, we are committed to driving meaningful change in gender equality across the FinTech industry. Through our initiatives, research, and thought leadership, we continuously advocate for increased representation, equity, and opportunities for women in financial technology. A key part of this commitment is our annual International Women’s Day event, which returns on 5th March 2025 under the theme FinTech Inclusion Includes YOU. This event is designed to spark conversations, challenge barriers, and create actionable change by bringing together industry leaders, male allies, and aspiring professionals. Featuring powerful discussions, networking opportunities, and inspiring speakers, it serves as a platform to showcase the impact of inclusion and highlight the steps businesses must take to foster gender equality. As a recruitment business, we understand that real progress requires more than just conversations—it demands action. That’s why we work closely with FinTech firms to help them build diverse and high-performing teams, ensuring that inclusion is not just a one-day initiative but a year-round priority. 

Defining the Stratospheric CEO

Toby and Georgie delve into what sets a “stratospheric CEO” apart from the rest. Georgie explains that these leaders occupy a rarefied space in the business world. They are not only visionaries but also have the stamina, adaptability, and resilience to sustain success over decades. A defining characteristic of these CEOs is their ability to navigate complex challenges while remaining focused on their long-term goals.

Georgie emphasises the human side of these leaders, highlighting their vulnerabilities and the personal challenges they face. Her book seeks to demystify the idea of the untouchable CEO by showcasing their humanity. These leaders are deeply people-focused, assembling exceptional teams and fostering cultures that prioritise trust, collaboration, and innovation.

The Importance of Culture in Attracting Talent

At Harrington Starr, we understand the critical role culture plays in attracting and retaining top talent. Georgie’s insights reinforce this idea, as she stresses that culture is not about superficial perks or token gestures. Instead, it is about creating an environment where people feel valued, motivated, and aligned with the organisation’s vision.

Georgie shares examples of CEOs who have built high-performance cultures by setting clear expectations, fostering accountability, and celebrating achievements. These leaders prioritise execution, measuring success through meaningful metrics rather than vanity numbers. By focusing on culture, they not only attract the best talent but also create workplaces where employees are empowered to thrive.

The Role of Focus and Execution in FinTech Leadership

One of the standout topics in the episode is the role of focus and execution in effective leadership. Georgie and Toby discuss how successful leaders turn ambitious visions into reality. Georgie explains that while many individuals have great ideas, the true differentiator lies in their ability to execute. Execution involves hiring the right people, setting clear goals, and maintaining a relentless focus on priorities.

Georgie introduces the concept of “execution jockeys,” individuals who excel at transforming strategy into action. These people are the driving force behind organisational success, particularly in an industry as dynamic and competitive as FinTech. For leaders, identifying and nurturing execution-focused talent is essential to maintaining momentum and achieving long-term objectives.

Resilience and Adaptability in the Face of Adversity

Resilience is a recurring theme throughout the episode, as Georgie reflects on how leaders navigate setbacks and failures. She believes that resilience, combined with realistic optimism, is a key trait of successful CEOs. These leaders view challenges as opportunities for growth and use their experiences to strengthen their organisations.

Georgie also discusses the importance of adaptability, particularly in an industry where change is constant. She highlights the need for leaders to embrace failure, learn from it, and adjust their strategies accordingly. This mindset not only fosters innovation but also creates a culture where individuals are encouraged to take risks and push boundaries.

The Human-Centred Approach to Financial Tech Leadership

Georgie’s philosophy is deeply rooted in the human side of leadership. She argues that the best leaders are those who genuinely care about their teams and create environments of trust and empowerment. This human-centred approach not only drives better business outcomes but also builds loyalty and engagement among employees.

Toby and Georgie discuss how this approach translates into FinTech recruitment and talent retention. Companies that prioritise their people are better positioned to attract top candidates who are motivated by more than just financial rewards. These organisations create a sense of purpose and belonging, which resonates with individuals seeking meaningful careers.

Insights for Emerging Leaders in FinTech

For emerging leaders and professionals in the FinTech sector, Georgie offers practical advice grounded in her extensive experience. She encourages individuals to focus on continuous improvement, embrace failure as a learning opportunity, and build strong networks of support. By cultivating resilience and adaptability, aspiring leaders can navigate the challenges of the industry and position themselves for success.

The episode concludes with Toby praising Georgie’s book for its accessible and insightful approach to leadership. He encourages viewers to explore Stratospheric CEOs for its practical lessons and inspiring stories. For those interested in learning more about Georgie’s work, she can be reached on LinkedIn or through her website.

The Importance of Realistic Optimism in Leadership

Another key takeaway from the episode is the concept of realistic optimism. Georgie explains that optimism, when grounded in reality, is a powerful driver of success. Leaders must balance visionary thinking with practical planning, ensuring their strategies are both ambitious and achievable.

Realistic optimism also involves surrounding oneself with a trusted network of advisors and team members who provide diverse perspectives. This collaborative approach helps leaders identify blind spots, refine their strategies, and maintain focus on their long-term objectives. Georgie believes that this mindset is essential for navigating the complexities of the FinTech industry.

Conclusion

In this engaging episode of FinTech Focus TV, Toby Babb and Georgie Dickins delve into the art of creating impactful leadership that drives transformation in the FinTech world. One standout topic is the interplay between leadership authenticity and adaptability. Georgie argues that leaders in today’s fast-paced industry must stay true to their values while continuously recalibrating their approach to meet shifting demands. This balance, she says, is critical for sustaining trust and credibility, especially during times of uncertainty.

What sets this conversation apart is its deep exploration of how leaders can blend emotional intelligence with strategic execution. Georgie describes the concept of “emotional contagion,” explaining how a leader’s energy and optimism can ripple through an organisation, inspiring teams and fostering resilience. She notes that the best leaders don’t just drive results—they leave a positive wake behind them, shaping a culture where people are motivated to excel.

For Harrington Starr, this episode underscores the importance of recruiting FinTech leaders who possess not only technical expertise but also the human-centred qualities needed to inspire and guide teams. It’s a reminder that in FinTech, where innovation and agility are paramount, the right leadership can be a game-changer.

At Harrington Starr, we are committed to supporting organisations in building exceptional teams and creating workplaces that drive innovation and excellence. By connecting FinTech businesses with top-tier talent, we help them achieve their goals and make a lasting impact in the FinTech sector.

This episode of FinTech Focus TV aligns seamlessly with Harrington Starr’s mission to connect the world’s leading FinTech organisations with top-tier talent. Georgie Dickins’ insights into leadership, culture, and talent attraction resonate strongly with our focus on helping businesses build high-performing teams. Her emphasis on creating purposeful workplace cultures and the critical role of execution reflects the challenges and opportunities our clients face in today’s competitive landscape. At Harrington Starr, we understand that attracting and retaining exceptional talent requires more than just a compelling job offer—it demands a clear vision, a strong culture, and human-centric leadership, all of which are explored in depth during this episode. By fostering these conversations, we continue to elevate the standards of FinTech recruitment and drive innovation within the sector.

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