Navigating a Dynamic Career: A Conversation with Caroline Sherry, CFO of Hostelworld

Difference Makers Discuss Live Episode 1

In an insightful conversation, Caroline Sherry, the CFO of Hostelworld, shared profound reflections on her diverse career journey, financial leadership, and the transformative role of Artificial Intelligence (AI) in the business landscape with Sinead Donovan, President of Chartered Accountants Ireland. In this article, we delve into key highlights from the discussion:

Chartered Accountancy – A Catalyst for Diverse Career Trajectories

Caroline Sherry embarked on her professional journey through Chartered Accountancy, a pivotal step that not only initiated her career but also laid the groundwork for an exceptionally diverse and dynamic trajectory. While deeply rooted in this discipline, her career transcended boundaries, spanning sectors from banking to FMCG and eventually to the tech industry. This diversification serves as a compelling testament to the versatility of a Chartered Accountancy foundation, dispelling any notion of a linear career path. Caroline’s journey stands as an inspiring showcase of the myriad possibilities unlocked by a robust Chartered Accountancy background.

Empowering through Qualifications and Financial Numeracy

Caroline noted the transformative influence of qualifications and financial numeracy, particularly leveraging her Chartered Accountancy background. As a seasoned CFO, she emphasised the pivotal role played by these attributes in shaping her leadership approach. One distinctive feature of Caroline’s leadership style is her adeptness at articulating complex financial details in a manner that transcends technical jargon. Her ability to communicate intricate financial topics resonates with diverse stakeholders, enhancing transparency, fostering collaboration, and demystifying financial complexities for a broader audience.

Micro Moments – Nurturing Resilience and Continuous Learning

In reflecting on her career, Caroline highlighted the profound impact of “micro moments,” seemingly inconspicuous instances that played a pivotal role in shaping her resilience and fortitude to confront challenges. These instances – often underestimated – have contributed significantly to a reservoir of experiences that fortify individuals, preparing them for the demands of leadership roles. Caroline advocates for a mindset of continuous learning, where every encounter, obstacle, or success becomes a source of knowledge. Her commitment to perpetual learning has been instrumental in her ability to navigate the dynamic landscape of the business world. Caroline’s journey exemplifies how the lessons distilled from micro moments serve as a compass for thriving amidst complexity, turning routine encounters into meaningful building blocks of expertise.

Navigating Imposter Syndrome

In a candid revelation, Caroline Sherry opened up about her encounter with imposter syndrome, shedding light on the ever-evolving journey toward self-belief. Despite her significant achievements, she acknowledged that imposter syndrome can persist, thus shining a light on the complex relationship individuals often have with their own capabilities and achievements. Caroline’s acknowledgment of imposter syndrome speaks to its pervasive nature, as the idea that a person doesn’t deserve their success or that their accomplishments are merely a result of luck rather than competence is a sentiment many high-achieving individuals grapple with. By recognising the ongoing nature of the journey to self-belief, Caroline has normalised a shared experience among professionals. Furthermore, Caroline drew attention to the critical role representation plays in mitigating imposter syndrome. Highlighting her journey in traditionally male-dominated sectors, she emphasised the importance of diverse role models. Seeing individuals who resemble oneself in leadership positions can be a powerful catalyst for overcoming self-doubt and fostering a belief in one’s capabilities. Beyond her personal narrative, Caroline advocated for systemic change in the form of increased diversity and inclusion. Breaking down barriers in sectors traditionally dominated by a particular gender requires intentional efforts.

Paving the Way for Gender Equality in Leadership – The Balance for Better Business Initiative

Caroline Sherry’s dedication to fostering gender equality is evident through her participation in the “Balance for Better Business” review group. The initiative is a driving force in advocating for gender balance, especially in senior executive roles across diverse sectors. Caroline emphasised the group’s commitment to addressing gender disparities, particularly in top-tier positions. By focusing on senior executive levels, the initiative aims to dismantle barriers and challenge preconceived notions about leadership roles being predominantly male.

The group’s commitment to accountability is showcased through the annual report it publishes, which benchmarks the current state of gender balance within Irish businesses. This report serves as a tool for introspection, allowing companies to gauge their progress and compare themselves against peers in Europe, fostering a sense of responsibility and transparency.

Caroline acknowledged the pivotal role played by the group in normalising the conversation around gender equality. While strides have been made, the need for continuous improvement remains. The initiative encourages a shift in mindset, making gender balance an expected aspect of organisational dynamics. Caroline’s involvement in the “Balance for Better Business” initiative extends beyond rhetoric, translating into tangible actions that contribute to reshaping the landscape of gender representation in leadership. Her insights highlight the multifaceted nature of this endeavour, ranging from accountability and benchmarking to addressing specific challenges faced by organisations.

The Challenge of Preserving Gender Equality Gains

Caroline Sherry recognised the positive strides made in gender equality but raised a poignant concern regarding potential setbacks, particularly in the aftermath of the COVID-19 pandemic. While the shift to remote work has introduced newfound flexibility, it has also given rise to questions about presenteeism and visibility, factors that may disproportionately affect female professionals.

The impact of remote work on gender dynamics is complex. On one hand, it has demonstrated that flexible and remote work arrangements can be effective, challenging traditional notions of how work should be structured. This shift has been particularly beneficial for working parents and individuals seeking a better work-life balance. However, Caroline expressed concern about the potential for regression. The pandemic has forced a re-evaluation of workplace practices, and while remote work has proven successful, it also brings challenges. The need for physical presence, especially in certain industries or roles, can inadvertently disadvantage those who opt for flexible arrangements. This is particularly relevant for women who may take maternity leave or parental leave, creating a potential visibility gap. Preserving gender equality gains requires a proactive approach from organisations. While remote work offers flexibility, there is a need to address the balance between flexibility and maintaining a visible presence in the workplace. It involves reassessing the importance placed on physical presence and cultivating a culture that values output over hours logged. Caroline’s insights shine a light on the delicate balance between embracing flexible work arrangements and ensuring that these do not inadvertently hinder progress toward gender equality. The challenge lies in maintaining the positive aspects of remote work while mitigating the potential drawbacks, ultimately fostering an inclusive work environment for all.

Encouragement for Future Generations

Caroline Sherry offered valuable insights for the next generation, emphasising continuous learning, adaptability, and resilience. She advocated for diverse career exploration, recognising the significant enhancement of skills and perspectives through varied experiences. Her advice promotes a growth mindset, urging individuals to approach challenges as opportunities for learning and leverage strengths in diverse professional landscapes.

The Role of AI in Modern Business

Caroline Sherry discussed the evolving technological landscape, particularly the role of AI in business. Hostelworld leverages AI to enhance user experiences, creating a dynamic social network predicting future travel trends. Caroline acknowledged the gender gap in the tech industry, highlighting the need for structural changes to ensure balanced representation.

A family legacy?

In the closing remarks, Caroline expressed openness to her children pursuing Chartered Accountancy, citing the strong work ethic and values instilled through her experiences. This sentiment reflects not only a personal connection but also recognition of the enduring principles and skills that Chartered Accountancy can impart to future generations – not least within her own family.

Season 5 of the Difference Makers Discuss Podcast by Chartered Accountants Worldwide heralds insightful conversations with global leaders, innovators, and change-makers. Offering diverse perspectives on critical issues, this season explores finance, sustainability, diversity, and technology’s role in shaping a dynamic future. Engaging, thought-provoking, and impactful discussions await listeners.

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