Waystone
Oran O’Connell
06 Aug 2025
Oran O’Connell, senior associate at Waystone, shares his journey into asset servicing, reflecting on regulatory insight, international experience and the importance of mentorship
Image: Waystone
Can you give me an insight of your personal journey into the asset services industry, why did you decide this was the career for you?
My interest in the asset services industry was driven by a natural interest in finance, global financial markets and international business. I started my career with Waystone by completing an eight month internship with the Structured Finance/Corporate Services team in Cashel, Ireland. This gave me early exposure to regulatory frameworks and cross-border transactions. I completed a bachelor in Business Studies at the University of Limerick, majoring in Risk Management and Insurance and later completed a postgraduate diploma in Applied Alternative Investment Funds from the University College of Dublin.
I had a major interest in the world of investment funds and as a result, transitioned into the asset management industry — first in Ireland and now in the Cayman Islands. The combination of analytical work, regulatory insight, and strategic oversight really resonated with me, making it a perfect fit.
What aspects of your job do you enjoy the most?
My role is enjoyable as it has an intersection between regulation and strategy. I enjoy being involved in the day to day oversight of fund operations and ensuring good governance and compliance with local tax regulations here in the Cayman Islands. There is a great deal of satisfaction in seeing how good governance practices can improve an entity’s day-to-day operations. Another aspect I really value is client interaction. Working closely with clients allows me to build strong professional relationships and gain a deep understanding of their structures, needs, and challenges. Every client is different, and tailoring solutions that align with both regulatory expectations and overall objectives keeps the role dynamic and rewarding.
How do you find your experience in the industry as a newer person, compared to those who are more established? Are there pros and cons to each?
Experience is invaluable in the funds industry. As someone relatively new to the industry, I have found it incredibly valuable to be surrounded by highly experienced independent directors. Their depth of knowledge and willingness to share insights has been instrumental in accelerating my learning.
It is very encouraging to be in an environment where questions are welcomed, and guidance is always available — it creates a strong foundation for professional growth.
While more established professionals naturally bring years of experience, a willingness to take such advice onboard should assist in influencing my ability to become more influential over time.
Have you noticed any misconceptions about the asset servicing industry? Is there anything in the industry you would like to see evolve or change?
Waystone has been fully committed to retaining young employees and giving every opportunity there is possible to kickstart my career. Waystone allowed me the opportunity to relocate from Ireland to the Cayman Islands, which has been an incredible experience. They also funded my further studies at the University College of Dublin, which I have been very thankful of.
A common misconception is that the various departments within asset servicing — such as risk and compliance, legal, anti-money laundering (AML), and business development — operate entirely independently of one another.
In reality, our work is highly integrated. These functions consistently collaborate and feed into one another to ensure seamless service delivery and robust governance solutions for our clients.
What is the training process of a new employee? Do you think it was beneficial to your role and others who may now be in the same position you were?
When I joined Waystone, I had the benefit of both formal training and hands-on experience. I was fortunate to work across different teams and regions — from fund risk in Ireland to Economic Substance and Fund Governance in the Cayman Islands.
That exposure gave me a holistic view of the industry. I absolutely think it was beneficial, and I would encourage firms to continue offering rotational or cross-functional learning opportunities for new hires.
In terms of your career, where do you see yourself in a decade?
In ten years, I would like to see myself having progressed further in the directorship space, taking on greater responsibility and contributing more strategically at the board level. I am particularly interested in expanding my reach across multiple jurisdictions, working with a broader range of clients and governance structures.
This kind of growth comes with time, experience, and most importantly, strong professional relationships. I believe the foundations for that are being laid now — by consistently delivering high-quality work, being proactive, and earning the trust of clients and colleagues.
I look forward to continuing to build those relationships and broadening my impact across the global financial services landscape.
What advice would you give to young graduates when entering the financial services field?
My biggest piece of advice is to gain as much on-the-ground experience as possible. There is no substitute for learning by doing — whether that is getting involved in client meetings, contributing to projects, or observing how different parts of the business operate.
At the same time, start building your network from the very beginning. The relationships you form early in your career will often be the ones that support and guide you for years to come. I have been fortunate at Waystone to work alongside exceptional professionals who are always willing to share their knowledge and encourage growth. That kind of support makes a real difference.
I also strongly believe that international experience is invaluable. Working in different jurisdictions broadens your perspective, enhances your adaptability, and deepens your understanding of global financial services — I would definitely encourage any graduate to take that opportunity if it arises.
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