Leaders Under 40: Amanda O’Brien

The past year at Markel saw a major reorganisation — expanding territories, reshaping teams and accelerating execution. Amanda O’Brien found herself at the centre of a rapidly shifting landscape. Overnight, the scope of her role as regional product lead for property and marine widened, and her team suddenly grew in size and complexity.

How she navigated that period says a lot about why she has been recognised as one of Intelligent Insurer’s Leaders Under 40 for 2025. Rather than trying to project certainty, O’Brien leaned into what she knows best: psychology, performance and people. (Click here to watch the full interview)

“It was incredibly challenging,” she recalled. “My team was looking to me for leadership and guidance and I didn’t always have the answers. And at times when I did, there were moments when I couldn’t share them yet. It was hard looking out at a team I care so much about and knowing they were stressed.”

Her background in psychology shaped much of her approach. “Every change brings opportunity with positives and negatives, and every change comes with risks and rewards.”

She also drew heavily from sports psychology — from Formula One team principals to classroom theories that she still revisits when pressure builds. “Listening to a Formula One team principal speak about change and opportunity really resonated with me,” she said. “There are a lot of parallels between finding success in business and finding success in athletics. I listen to podcasts, I read articles, I even go back through textbooks from sports psychology classes when conditions are challenging.”

A career built on taking chances and caring deeply

O’Brien’s journey into the industry began, like many, by accident rather than design. “I wish I had some divine, altruistic story about being destined for underwriting,” she joked. “But I was fortunate to have insurance choose me.”

Fresh from UC Irvine in a difficult economic climate, she landed her first role at Swiss Re and suddenly faced a decision to relocate from Orange County to San Francisco.

“It was a big decision coming straight out of college,” she said. Her parents’ advice shaped everything that followed: home is always here; go out and take chances.

She did — and the sector quickly drew her in. “The more I learned, the more I realised I wanted to pursue it,” she said. “Fifteen years later, I honestly can’t imagine doing anything else.”

Her career, she added, has been defined by twists, learning, and the people she has met along the way. “Some of my dearest friends are people I met in this industry.”

“Being green isn’t bad. It just means you bring a different perspective.”

Build cultures where people thrive

For O’Brien, leadership is not about control. It’s about creating the conditions for people to do their best work.

“People perform best when they feel comfortable and confident,” she said. A core part of her philosophy is creating psychological safety, a space where people feel able to contribute, challenge or try new things without fear of embarrassment.

“I so admire the fearlessness of the next generation.”

“If we can create an environment where people feel confident suggesting things and taking chances, what starts with the field builds up and has a more lasting impact.”

It is a principle that shaped how she guided her team through Markel’s transformation. Stability, openness and honest communication became essential to keeping people engaged. “If we create a culture people want to be part of, they take pride in its success.”

‘Being green isn’t bad’

O’Brien is deeply energised by the younger cohort entering the market. “I so admire the fearlessness of the next generation,” she said. “They don’t know how to do badly because they’re fearless, and I admire their confidence.”

The environment she began in looked very different. “When I started, the vibe was more ‘speak when spoken to’,” she said. “It was made clear I didn’t have the technical knowledge — and I didn’t. But being green isn’t bad. It just means you bring a different perspective.”

That perspective, she believes, is exactly what the industry needs. “Sometimes the established way isn’t the right way. What got us to where we are today may not get us to where we want to go next.”

Her admiration for early-career talent shapes how she leads, mentors and builds culture. She sees coaching and development not as a HR function but as a strategic lever.

“If we focus on listening and getting their buy-in, we have a great retention tool,” she said. “People see the impact they can have and they feel invested.”

Despite her seniority, O’Brien describes herself as a perpetual learner, someone who actively works on being “the best people leader I can be.”

She works on managing pressure with intention, maintaining calm during moments of volatility, and keeping perspective. “There’s always a new loss to come along and humble you when you think you know everything,” she said. “I like that about this industry.”

Her commitment to learning is matched by an equally strong commitment to paying it forward. “I had excellent mentors early on,” she said. “Having had those people in my corner, I feel a real need to pay it forward.” She still seeks guidance from those mentors today.

Advice for the next generation

Her message to rising professionals is simple, modern and deeply empathetic.

“Just don’t be afraid to take chances,” she says. “Sometimes all you have to do is be brave and jump. You can always pivot. Nothing is permanent. There is no colossal mistake that’s going to be career-ending.”

Curiosity, courage and care — those traits sit at the centre of her leadership and what she hopes the next generation embraces.

Click here to watch the full interview:

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