A head start in legal AI

Fluency in innovation

These were the early days of what would become the Markets Innovation Group (MIG), giving Cairistiona a front-row seat in the firm’s pioneering use of legal tech. “Technology went on to shape the direction of my career. I was lucky enough to be involved in really exciting projects, just as David was building the MIG team from the ground up.”

As part of MIG, she worked on global regulatory change projects, deploying technology to assist clients—using large language models to review documents at scale and designing the architecture for automatically generated documents based on industry templates. She bridged the law and tech gap well before the launch of ChatGPT.

“I learned to speak both languages—law and tech. This has made me a better lawyer and equipped me to thrive at a time where the legal industry—and really, the world—is so focused on technological innovation.”

During her time at A&O, she gained foundational coding skills through “Code First for Girls”, introducing her to Python, SQL, C#, and JavaScript. This early exposure helped her build a basic literacy in technology and deepened her interest in legal innovation.

The skills she developed at A&O continue to serve her today, particularly as lawyers increasingly engage with new technologies such as learning how to prompt effectively.

“When prompting you must give very explicit instructions to get the best output. You must go in knowing what you want it to achieve. It isn’t perfect, and you must always check and review the results, but I have been surprised by how it can direct your thinking and make you consider more deeply the problem or task at hand.”

A global upbringing, a global network

Born in the UK, Cairistiona spent much of her childhood abroad, living in France and across the U.S.—from Boston to California—before returning to England for boarding school at age 13. This international upbringing sparked a curiosity about different cultures and ways of working.

That global perspective carried into her professional life. As a trainee, she spent six months in the derivatives team in Hong Kong and later, as an associate, she was seconded to New York, where she is now based. “I feel very lucky to have worked in three of the world’s biggest financial hubs.”

Hong Kong introduced her to Asian markets and the importance of cross-border work. The city’s energy and international outlook sharpened her ability to navigate complex transactions and adapt quickly to different working styles. New York brought intensity and commercial focus, helping her develop a more strategic mindset, particularly in her transition to in-house counsel. It also offered proximity to family and personal grounding. These experiences mean she is comfortable working across jurisdictions and cultures.

Cairistiona is adept at maintaining connections. She remains plugged into the firm’s network, keeping in touch with former colleagues and friends in London and New York. Her original trainee group remains close-knit, reconnecting whenever Cairistiona is in London.

“It’s not just been a place that shaped my career, but also me as a person. I have a lot of great friends from my time at A&O.” Post-merger, Cairistiona has seen the New York derivatives team grow, offering support across a broad spectrum of legal issues. She values working with legacy A&O and legacy Shearman partners.

The move to banking

During her seven years at A&O, Cairistiona seized opportunities on offer, including a ten-month secondment to Bank of America (BofA) in New York—deepening her client relationships and broadening her commercial perspective. “It was a great opportunity to interact directly with clients, especially as a mid-level associate. I also got to know BofA, its culture, and its people.”

It was soon after that secondment, in 2022, that she joined BofA full time. Having enjoyed her time at the bank and amid shifting priorities, the move was a natural next step. She was also excited to work alongside fellow A&O alumni. This included her manager, Ruth Arnould, as well as Sandy Tapnack, Tyler Kinder, and Owain Markham, who are all part of the bank’s fixed income derivatives legal team.

She says collaborating with dynamic, experienced and motivated individuals with diverse perspectives is what she most enjoys, while sitting alongside the business has deepened her understanding of strategic priorities.

Cairistiona reflects that working in-house is distinct from acting as external counsel. “We are right there with the business. It feels more strategic and commercial, and we get to understand the big picture.”

In-house counsel is embedded in the organization. The role spans in-depth legal analysis of new regulations and their impact on the business; drafting transaction documents; working with external counsel; identifying and escalating risks; and engaging with internal stakeholders. This proximity to the business requires a strong grasp of commercial priorities and the ability to navigate complex, cross-functional issues.

Interrogating technology to gain the best output

Cairistiona sits on BofA’s Legal and Public Policy AI Council, which evaluates emerging technologies, explores their potential applications, and educates the legal department on effective and responsible use. “We’re exploring how we can use AI but always through a lens of risk management and with the understanding that humans must be accountable for the output.”

With the rapid proliferation of AI tools, she emphasizes the importance of establishing clear guardrails to balance innovation with risk. Institutions must ensure high-quality data inputs, teach effective prompting techniques, and understand the limitations of these tools. The goal, she explains, is to enhance—not replace—human capability.

Her time on the MIG team at A&O instilled a critical approach to legal technology. One formative experience was a “Bake Off,” held before the rise of generative AI, where the team tested two tools in parallel to assess their ability to review and extract data from documents.

“We learned which questions to ask of the tool, and how best to get it to perform and, more importantly, ensure accuracy. When you’re interrogating a tool, consider its purpose, the output, and the longer-term plan.”

This ability to scrutinize technologies effectively and ask the right questions has equipped Cairistiona to identify tools that can genuinely support legal teams. “What we definitely don’t want is to use a tool that produces poor-quality outputs.”

Through her work on the steering committee, she collaborates with lawyers globally and has found that many are seeking solutions to similar challenges. For example, when new legislation is introduced, lawyers must quickly distill its impact. AI can assist by generating concise summaries, but human oversight remains essential, given the risk of hallucinations.

Another common pain point is negotiating templated agreements. These can be time-consuming, but with the right training, AI can review and mark up standard terms in minutes.

“The legal industry is being significantly disrupted by new technologies. We must adapt. I see it as a way to boost efficiency and enhance our roles rather than replace the legal function.”

Cairistiona’s career reflects a blend of legal expertise, global experience, and a forward-thinking approach to technology. Her early exposure to legal innovation continues to shape her work, as she helps guide the responsible use of AI and support legal teams across the business.

Reconnect with Cairistiona Simmonds.