“Beyond the Desk”: Celebrating the People Behind the Expertise.
In this series of interviews, we shine a spotlight on our colleagues who are not only exceptional insurance professionals but also inspiring individuals beyond their professional roles. These stories reveal the human side of the industry—highlighting their passions, commitments, and the values that drive them both inside and outside the workplace. Join us as we explore the journeys, insights, and personal stories of those who exemplify excellence, resilience, and compassion in every aspect of their lives.
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Cassandra Rotunno, Senior Underwriter, E&S General Liability, Americas exemplifies the talent and commitment that underpin our success. Her journey, achievements, and leadership reflect the dedication and expertise that drive our team forward. Her story not only underscores her individual accomplishments but also highlights the collaborative spirit and excellence that characterize our organization.
Q: Could you share your journey into the insurance industry and what initially drew you to underwriting and why E&S?
Cassandra: My journey into insurance was motivated by a passion for analytical thinking combined with relationship management. I was drawn to underwriting because it offers the opportunity to evaluate complex risks, develop innovative solutions, and collaborate closely with brokers and clients. It’s an intellectually stimulating and dynamic field that continually inspires me to grow and improve. The E&S space is incredibly interesting – it’s the fun, unique, cutting-edge clients and exposures that push our work beyond the standard idea of what someone thinks when they hear “insurance”. Every day I am challenged to research a client’s operations or get creative in getting a deal done because every opportunity is unique. This work keeps me on my toes in the best ways!
Q: You’ve recently achieved remarkable milestones, including doubling your team’s business goals for 2024. What strategies have been instrumental in reaching these impressive targets?
Cassandra: Success has come from a client-centric approach, emphasizing a deep understanding of client needs and proactive engagement. Building trust through transparency and creative problem-solving has been key. Additionally, mentoring and developing my team has fostered a culture of excellence that drives collective performance and results.
Q: Mentorship and talent development seem to be central to your leadership style. Why do you believe mentoring is so essential?
Cassandra: Mentorship is fundamental because it helps cultivate the next generation of underwriters. Sharing knowledge, providing guidance, and nurturing confidence are vital for their growth. It also fosters a culture of continuous learning and excellence, which is critical for the sustainability of our industry and the success of our teams.
Q: You recently transitioned into a new role as a central team leader for E&S, General Liability. How has this evolution influenced your focus and priorities?
Cassandra: The transition has been both exciting and rewarding. My main priorities now are to enhance team performance, support ongoing development, and promote collaboration across departments. I also aim to maintain our innovative edge in a rapidly changing market, all while upholding our core values of integrity, service, and resilience. The E&S marketplace is incredibly dynamic but fruitful relationships are steadfast and thrive on consistency; it’s so important to help my team be nimble in their underwriting while building deep relationships with our broker partners. There is no black-and-white answer in E&S underwriting: each risk is unique and filled new challenges, embracing this and showing up energetically for the market leads to fun “wins” and lasting profitability.
It’s incredibly rewarding to contribute to empowering vulnerable populations, providing them with resources and support to rebuild their lives.
Q: Your reputation for collaboration and creative problem-solving is well-earned. Could you share an example where you faced a significant challenge and how your approach led to a successful outcome?
Cassandra: Certainly. One notable example involved a complex hospitality deal that was at risk of falling through. Rather than accepting rejection, I worked closely with the broker and underwriters to explore alternative coverage options and negotiate terms that satisfied all stakeholders. This required strategic thinking and persistence, ultimately allowing us to retain the client and strengthen our relationship through innovative solutions.
Q: Outside of your professional achievements, you’re deeply involved in community service. Could you tell us about your work with Styled with Strength and why this cause is meaningful to you?
Cassandra: Absolutely. Supporting women and children escaping domestic violence through Styled with Strength | Community | West Fargo, ND, USA is a cause I am deeply passionate about. It’s incredibly rewarding to contribute to empowering vulnerable populations, providing them with resources and support to rebuild their lives. Volunteering in this space aligns with my personal values of kindness, resilience, and advocacy—principles I also strive to bring into my professional life.
Q: How do you balance your professional responsibilities with your commitments to family and community involvement?
Cassandra: Balancing work and personal life requires effective time management and staying present. I am fortunate to have a supportive family and a community that keeps me grounded. Working closely with my kids’ school clothing and food pantries and supporting causes such as Styled with Strength help me stay connected and energized, which in turn enhances my focus and dedication at work.
Q: You’ve spoken about the influence of mentors who have shaped your career. What qualities do you most admire in those mentors, and how do you incorporate those qualities into your leadership?
Cassandra: I admire qualities like kindness, humor, resilience, and adaptability. These traits foster trust and open communication. I strive to embody them—listening actively, remaining flexible, and approaching challenges with a positive attitude. Leading with integrity and genuine care for my team and clients is central to my leadership philosophy.
Q: Finally, what advice would you give to aspiring underwriters and professionals seeking to excel in this industry?
Cassandra: Stay curious, proactive, and committed to continuous learning. Recognize the power of collaboration and kindness. The industry is always evolving, and those who adapt while staying true to their values will thrive. Seek out mentors, embrace growth opportunities, and approach your work with passion and resilience.
