| CAREERS BLOG
Beatrice Dela Pena
October 2026
My name is Beatrice Dela Pena, and I’m the Chief Underwriting Officer for Personal Lines at Tower Hill.
My Role and Background
My career in insurance started shortly after graduating high school, when I joined an independent agency. I started as a receptionist, and after getting licensed, I became an agent. When another agent unexpectedly left, I was asked to run an office. That gave me an early look at what it meant to be a personal lines agent while also running an office.
From there, I joined a large national carrier, where over two decades I held leadership roles across Sales, Service, Underwriting, Claims, Agency Operations, Process Improvement, Technology and Product. Each role expanded my love of the industry and strengthened my underwriting knowledge.
Along the way, I completed my Executive MBA and several insurance designations, including my CPCU (Chartered Property Casualty Underwriter). I also began pursuing a doctorate in Strategic Leadership, which I expect to complete this year. I am excited for my next chapter here at Tower Hill!
As Chief Underwriting Officer, no two days are alike because the market and risk landscape are always changing. While the work changes, my focus is always on building and collaborating across the organization to improve our underwriting strategies and processes.
Our team works every day on underwriting requests submitted by agents on behalf of our members, as well as requests triggered by our processes. We work together to effectively underwrite policies while providing high-quality, efficient experiences and supporting Tower Hill’s long-term goals.
The most rewarding part is working in a team to solve problems by connecting the dots between data, trends, market conditions and underwriting processes. Underwriting is dynamic and always evolving, which keeps the work interesting and rewarding.
And when it comes to leading my team, it really comes down to one thing: it’s the people. We have an amazing group of talented, experienced underwriters and leaders at Tower Hill, and working together to solve problems and evolve our strategies is one of my favorite parts of the job.
It’s been a lot of learning, which I love! There are so many experts across Tower Hill who have been tremendously helpful as I get to know the people, the business and our processes. I’ve spent a lot of my time focused on new products for 2027, getting to know people and getting acclimated. It’s busy and exciting.
“I’m honored and excited to be part of a team known not just for great products, but also for service, stability and professionalism.”
My Leadership Philosophy
Over the years, I have morphed from a servant leader to an authentic leader who realizes that leadership is a never-ending journey. I have a high level of self-awareness, and I believe it’s important to continue growing as a leader.
For me, that means leading with openness and transparency to build trust and psychological safety. I want to create an environment where people feel invited and welcomed to bring new ideas and different perspectives to the table. That is how we learn and innovate.
Staying true to my ethical values and beliefs is also tremendously important to me, both as a leader and as an underwriting professional. There are two important lessons I’ve learned throughout my career. First, it’s important to stay grounded in your strengths while also stepping outside of your comfort zone to stretch your skills and mindset. That can be difficult because leaders sometimes feel like they have to have all the answers. But growth comes from taking risks and having new experiences.
The second is the importance of collaboration. Working with others allows us to create better, shared solutions, and focusing on the team and building the skills of those around you is essential as a leader.
Why Tower Hill?
Before joining Tower Hill, I had heard great things from several people I knew and trusted. I was also familiar with Tower Hill as a consumer. I had always been happy with my own policy and knew Tower Hill as a reputable, well-respected insurer in Florida.
When the opportunity to become Chief Underwriting Officer came along, along with Tower Hill’s 2027 growth priorities, it felt like an excellent fit both personally and professionally. It was a big decision for me because I’m a very loyal person, but it was the right decision, and I’m grateful to be here.
I already knew Tower Hill had a strong culture and a rich history, but one thing that surprised me was how consistent the stories and feedback were from employees across different departments. Almost immediately, I felt connected to the culture and appreciated the warm welcome I received from people throughout the company. It exceeded my expectations, and my expectations were already high.
When I think about what sets Tower Hill apart, it’s back to the people. Our employees, agents, customers and other partners have great relationships and reputations because of the way they work together. I’m honored and excited to be part of a team known not just for great products, but also for service, stability and professionalism.
Life Outside of Work
Outside of work, my life is pretty busy too! I’m a veteran of the United States Army Reserves. In my 20s, I served for nine years in a finance MOS and ended my service as a Staff Sergeant (E6). I loved my military experience, and it remains a big part of my identity and leadership.
I also tell people that outside of work I’m a personal assistant to my two girls, Olivia (11) and Ava (10). Their lives are busy with school, cheer, tumbling and more, so when I’m not at work, I’m usually at one of their activities or helping with schoolwork and sports. Really, anything they need, I’m there.
I’ve always enjoyed teaching and helping others, too. When I have the opportunity, I teach part-time as an adjunct professor at a local college in Lakeland, where I teach finance, accounting and risk management. I also occasionally teach first grade catechism at church, but that one requires much more patience!
If I weren’t in insurance, I would probably still find myself in academia, teaching and researching business and leadership. I love learning, and I enjoy sharing that knowledge with others.
Looking Ahead
Tower Hill has become a leader in the property insurance space during a difficult market, and I’m excited about building on that strong reputation and foundation in 2027 as we expand into additional products.
That work also means continuing to collaborate with our agents and other key partners. Our ability to work together allows us to offer stable, affordable products to consumers, and I believe insurers play an important role in the communities they serve.
Our underwriting team and I are looking forward to evolving our underwriting approach and incorporating new products and systems in 2027. As we continue to evolve, the fun part will be working together as a team with our key partners.