Listen to this articleMany businesses and investors choose to stay within the familiar boundaries of their home nation or continent, but it’s rare for them to achieve the heights of success reached by their more internationally-minded peers. To find the most success in the modern business world, one has to operate on an international level, with few industry exceptions. When it comes to insurance and fintech, this is even more important, especially in the modern world of machine learning, AI, and technology-driven solutions.
Gavin Southwell understands this personally; As a proven executive and leader in the insurance and fintech industries, Southwell has demonstrated significant experience in all aspects of capital market transactions. He sold his prior company privately at significantly above trailing share price, he’s negotiated large debt facilities, and he has experience running an SPAC process. Southwell has worked with some of the largest InsureTech exits in history, with previous customers including leading names in retail, financial services, and transportation.
After spending twenty years working in investment banking and insurance technology in the London area, he transitioned into health and life insurance technology work in the United States. The decision to bring his expertise overseas was driven by a multitude of factors, both personal and professional, but the driving motivation was twofold: it was an opportunity to grow and address market inefficiencies, and it was a chance to meaningfully help people protect themselves and their families. The move proved fruitful, as Southwell rapidly became the CEO of and President of the #1 Fastest Growing Publicly Traded Company 2017-2019, as rated by Fortune Magazine), and has since taken that success elsewhere. Today, he’s working as an advisor and investor to technology focused growth businesses.
Career-Shaping Moments
Like any business leader, Gavin Southwell has his share of influences and pivotal moments. Originally from a poor region of Northern England, Southwell’s move to London and subsequent professional success was incredibly meaningful. His career started with a privately owned insurance broker, then within a few years grew to become the largest one in the world, winning London Broker of the year among other awards. These were the first seeds of his international expertise, with clients ranging across Latin America, and when the company was later sold to private equity he was able to quickly jump to the next opportunity.
“I was part of the team that built the world’s first Quote/Buy/Print insurance business, we sold that to the world’s largest insurance company, and they used the model and the tech we built for personal lines around the world,” Southwell says. “At Beazley, we were the first Lloyds Insurance company to be rated Strong for Risk Management; as the Risk Manager, this was a great achievement.”
The early stages of his career were marked by the presence of multiple inspiring figures and mentors. One of these figures was Andrew Beazley, Co-Founder of Beazley Plc, whogave Southwell his first big role at a young age and taught him how to build on his strengths instead of hyperfixating on solving weaknesses. Since moving to the US, Southwell has also been fortunate enough to meet with leading business leaders on multiple occasions, including his greatest inspiration: Warren Buffett. He was impressed by the easy manner and intelligence of the, at the time, richest man in the world.
“He was very smart, fun and friendly; in that crowd that really stood out to me,” Southwell recalls. “I’ve been lucky to work with positive high energy people who want to build good businesses and address market challenges through technology and improving processes.”
After working for decades in the London area, personal tragedy became a motivator for change. The early death of his son was a transformative moment, one that paired grief with an extended period of work supporting charities for families in similar situations. It was a time that redefined his relationship with business for the better; making good deals and investments is good, but success became measured in part by how much a business did good in the world and helped society’s most vulnerable.
“A defining moment was when I realized that there are more important things than money, that bad things happen, and it’s how you react to that darkness which will define you,” he says. “I’m fortunate really. Everything before brought me here, so although there have been highs and lows, that’s all part of it.”
A Modern, Human Conception of Success
In light of the many twists and turns of his life and career, Gavin Southwell has a nuanced and multifaceted definition of success, both professionally and personally. His family-first perspective paired with his core values of resilience, hard work, and helping others have created a paradigm with the goal of benefitting as many people as possible, be they clients, shareholders, employees, or (through charity) the people of his community. It’s not, and has never been, about being famous or well known—it’s about doing good and doing his best.
“I care about family and friends, and I want them to know that I’m doing well and living a good life, that just means trying to be happy and content,” Southwell explains. “There is always more to do, things we would have changed or done differently. Make it count right now, do your best, and that to me is success.”
This focus on positive change has led to real results both in and outside of the office. His companies have created thousands of jobs by training blue collar workers into licensed insurance agents, with a high rate of diversity too—roughly 70% of the staff were female, and 75% represented minority populations. Top performers would be regularly rewarded with vacations and bonuses on top of regular pay and benefits, which consistently made a positive impact on their lives. This goes without mentioning the tens of thousands of people Southwell’s company and staff helped connect to healthcare in the United States’ infamous healthcare system.
“I used to keep a folder on my desk of the emails and letters we would receive from people whose lives have been saved by the healthcare we had been able to connect them with,” Southwell remembers.
Outside the office, Gavin Southwell has been a significant contributor and partner to multiple charities over the years. He organized and completed cycling events across the UK for years, and is still closely involved with a Tampa-based charity operation. Beyond his personal contributions, his companies have supported several charities and have consistently made community work part of their personnel development policy.
