Getting to Know the Aspen Investment Team

Headed up by Aspen Group Chief Investment Officer, Aileen Mathieson, the Investment team is considered one of the core pillars of value generation for our shareholders, providing a sustainable and stable base against which we can manage the underwriting business. We recently asked Aileen to describe some of her team’s achievements during a recent interview.

Please share some highlights you’ve achieved in 2025:
In 2025, the Investment team was named the “Property and Casualty Insurance Investment Strategy of the Year” winner at the Insurance Investor European Awards in London, marking the second consecutive year the team received this award in this category.

Our team also won both the “Property & Casualty Insurance Investment Strategy of the Year” and “ESG Investment Strategy of the Year” at the Insurance Investor North American Awards in New York City, further underscoring the consistency and strength of our investment strategy.

These awards reflect our investment income growth at Aspen of more than 16% since 2021, our book yield of 4.05%, (+210bps increase) and our total return of 5.04% (+521 bps improvement).  I’m also proud to note that this growth was achieved while maintaining a high-quality fixed income portfolio rated AA- for Aspen.

What is the team’s approach to achieving success?
Our approach is to collaborate closely with our outsourced managers, viewing them as an extension of my investment team with near-daily communication. This enables agility in identifying and executing opportunities. In 2025, we identified tactical rotations and took an active duration mismatch going into the year, which generated an additional 10% on recurring Net Investment Income.

Our track record of delivering sustainable investment returns was pivotal to Aspen’s achieving a successful upsized IPO on the New York Stock Exchange and the subsequent acquisition by Sompo and S&P ratings outlook upgrade – all of which underpinned our team’s direct contribution to shareholder value and financial strength.

How does the Investment team harness innovation, expertise and agility to achieve its goals?
Our multi-disciplinary team optimizes returns by utilizing innovative operational and structuring solutions across multiple jurisdictions to deploy our strategic asset allocation. Under my direction, the team has developed a comprehensive approach that optimizes return while strictly adhering to these constraints, enabling diversification across multiple asset classes (e.g., equities, private credit, structured products, and alternatives).

Additionally, we have designed a flexible multi-class private credit approach instead of fixed allocations, introduced EFTs for smaller portfolios, established a proprietary ESG scorecard and developed bespoke benchmarks for restricted and unrestricted portfolios to forensically attribute manager performance. By using a variety of advanced structures to achieve optimum access and having investment accounting and operations sit within the team, we are ensuring agility and continuity across the functions.

What are some of your priorities for 2026?
Continuing to position Aspen’s investment management strategy as a major contributor to the successful execution of the Group’s business plan, including the upcoming acquisition, remains a primary priority for the team. It’s important we remain working in a way that is consistent with each of our business lines and the various company requirements that sit within our Group.

We also maintain the ongoing integration of ESG in our investment strategy, following Aspen becoming a signatory of United Nations Principles for Responsible Investment (UNPRI) in 2023. It’s important to both my team and me that we continue to influence Aspen’s approach to investment management, assess the progression of the pathways framework and work together to further advance our responsible investment practices where relevant.

Last year, you were named a 2025 Elite Woman by Insurance Business, what advice can you give to other women starting out in Investments?
At the time, I had no idea I had even been nominated! It was quite humbling, given the women also on the list announced during International Women’s Month last year. I was truly honored to be recognized among such an inspiring group of women who are making significant impacts in the insurance industry.

For those starting in investment management, I would say not to be afraid to build a network and use it. Also, have someone as a sounding board to talk through you any opportunities or challenges you might be facing.

To succeed in the longer term, you must have the courage to challenge the status quo, which goes hand-in-hand with having the confidence to back your own convictions and trust in your ability. I have found that making the right decision does not always mean making the most popular one, so you must be prepared to combat criticism and remain steadfast in your decisions, while of course being open-minded to the views of others.

During my career, the CIO role has evolved extensively, and my responsibilities have grown considerably. For instance, I collaborate more with regulators, rating agencies, industry groups and other stakeholders. In addition, there is increasing complexity and an expanding scope of assets that insurers can allocate, together with the growing emphasis on ESG. While these factors have brought changes to my role, it’s important to recognize that it’s an opportunity to innovate, learn new ways of doing business and have your voice heard in areas you may not have engaged in previously.