Ben Schiffman – Crum & Forster

Ben Schiffman’s journey at Crum & Forster has been a study of leadership, adaptability and commitment to both his craft and his team. As senior vice president and chief counsel for Crum & Forster’s Surplus & Specialty Lines division, he has built a career that merges the rigorous demands of the law with a deep understanding of the insurance industry. But for Schiffman, the role goes beyond simply knowing the law; it’s about partnering with the business to ensure success.

Ben Schiffman | Crum & Forster | Senior Vice President and Chief Counsel, Surplus and Specialty Lines

When Schiffman took on this role in 2020, he was part of a team of one. He hit the ground running and set out to build a legal team to support the division, rapidly expanding its footprint in the specialty insurance sector.

“I went to the president and the COO, presented the business plan, and demonstrated why it was necessary,” he recalls, reflecting on his initiative to grow the legal team. Today, that team consists of 10 people, including three attorneys. Six of them, together with Schiffman, are based out of Crum & Forster’s headquarters in Morristown, New Jersey, while the rest operate from locations throughout the country.

Crum & Forster has a history of over 200 years and provides insurance products in the property and casualty, surety, credit and accident and health sectors.

Schiffman says that modern technology and a cohesive group of good people have made it easy to stay connected despite geographical distances. Regular meetings, from weekly check-ins to larger monthly group sessions, help Schiffman ensure everyone remains in sync. These monthly meetings are often held in person, and the team convenes at least once a year for an off-site retreat. For Schiffman, these gatherings aren’t just about work but about building relationships.

“I’m a firm believer that we’re all here to work, but we’re also here to get to know each other in social settings,” he says. From attending sporting events  to sharing meals, we value these opportunities to strengthen collaboration and camaraderie.”

A new insurance landscape

Schiffman’s leadership extends far beyond managing his legal team. He is deeply involved in product development, working closely with his colleagues to develop and rewrite insurance forms and endorsements and ensure regulatory filings are completed accurately. He also oversees the legal collection team, navigating the complex world of collections and bankruptcy cases. For Schiffman, in-house work isn’t about sitting on the sidelines. It’s about being actively involved in the business and finding ways to help the company meet its goals while navigating legal and regulatory hurdles.

“If you don’t understand the actual business and only know the law, that isn’t going to help advance the ball,” he explains, emphasizing the importance of understanding the industry’s nuances. “My approach is proactive, always looking for opportunities to assist.  We are not here just to avoid problems but to find creative solutions to drive the business forward.”

One of the most exciting areas Schiffman and his team work on is developing insurance programs for the emerging gig and sharing economy markets. This space includes a variety of peer-to-peer networks, food delivery, and ride-share platforms.  What makes these sectors challenging from an insurance perspective is that they tend to operate through unique and highly sophisticated technology platforms that require different levels of insurance for various aspects of the operations at different points in time, often based on the user interface with the respective technology. Crafting policies that fit these markets, such as separate coverage for the networks compared to the renters or for a platform and its drivers once they accept a ride or delivery assignment, requires innovative thinking and a deep understanding of the legal and business landscapes.

“This is particularly challenging on the regulatory front since we are often confronted with technology and insurance concepts that the regulatory authorities have not yet had an opportunity to address,” Schiffman explains. “We’re crafting these policies to fit the market while ensuring that we do so in a regulatory-compliant manner.”

Schiffman’s role involves much more than the traditional aspects of corporate law. His work often necessitates embracing emerging technologies while partnering with Crum & Forster’s digital teams to develop insurance products and internal portals to manage them. A good example of this is Crum & Forster’s TripExcess product, which was designed to cater to an emerging need in the commercial trucking insurance space to provide truckers with excess auto liability coverage for specific trips on an on-demand basis.  Schiffman led a team that developed the insurance forms necessary for this risk and navigated the company through the complex web of legal and regulatory steps required to provide such a product through an online portal in all 50 states.

“TripExcess is a great example of how we partnered with our business leaders and technology partners to create, market and deliver an on-demand insurance product through a modern web-based platform while navigating many legal, regulatory and compliance issues. We even successfully procured two US patents for our work on TripExcess, the only two patents for Crum & Forster in its 200-year history,” Schiffman explains.

He’s also highly involved in compliance, particularly in California, where regulations are notoriously challenging.

Finding his path

Schiffman didn’t foresee the transition from working at a Manhattan-based law firm to becoming an in-house corporate insurance counsel. However, his desire to be a successful attorney gave way to his natural aptitude for leadership and strategy. Now, as a “business guy sitting behind a desk,” Schiffman has embraced his role as a partner and collaborator within the company. His Orthodox Jewish faith also plays an integral role in his life.

“As a religious person, I believe that everything I have accomplished and that I will ultimately achieve is a gift from God, which I am eternally grateful for,” he says, speaking to the success and meaning he’s found in his personal and professional life.

Even with years of experience, Schiffman knows the value of collaboration and seeking advice. He maintains a strong network of outside attorneys to consult on specialized issues, never hesitating to ask questions when needed.

“Much better to raise your hand and ask a question instead of just taking a guess,” he says, a philosophy that underscores his belief in the power of collaboration and support.

Schiffman’s philosophy is clear: it’s easy to say no, but it takes confidence and courage to say yes. This mindset has allowed him to build a team, foster collaboration across departments, and help Crum & Forster navigate an ever-changing landscape. In his nearly 12 years with the company—he rose to his current position in January 2020—he has seen the division grow to the second largest, with over 500 employees. His work is grounded in his belief that being an effective in-house attorney requires more than just legal knowledge; it requires an understanding of the business and a willingness to partner with business leaders to achieve the company’s goals.

For Schiffman, who earned a degree in philosophy, politics, and law from Binghamton University and a JD from Brooklyn Law School, it’s all about using his talents to find ways to help the business succeed. In doing so, he has built a legal department that is as dynamic and forward-thinking as the company it serves.

“I look forward to continuing to provide Crum & Forster with the strategic legal guidance necessary for it to continue to grow and thrive in this fast-paced competitive environment. I truly enjoy being part of such a great company and am grateful that I have such a great team that helps me every step of the way,” Schiffman says.