The Iron Women of Westchester

Left to Right: Cate Whiddon, Westchester SVP Railroad; Jill Anderson, AVP Railroad; Angie Han, Senior RR Underwriter; Abbey Waldrop Roberson, RR Underwriter; Sydney Burrin, Chubb Associate.

How gender diversity and inclusion helped nurture our insurance relationship with Genesee & Wyoming Inc.

Women are enjoying a larger presence working at and with our nation’s railroads, not that they haven’t played important roles in the past. But like other industries long controlled by men, opportunities to get in at the ground floor and climb the rungs of success are becoming more available to women.

Kathryn “Katie” Farmer, Railway Age’s 2023 Railroader of the Year, exemplifies this possibility. The first woman chief executive of a Class I railroad, she joined Burlington Northern Railroad in 1992 as a management trainee. She rose through the ranks, holding positions in operations, marketing and finance. Succeeding Carl Ice, she became President and CEO in 2021.  Another female CEO, Kate Luce, leads Mississippi Export Railroad, ascending to the position at the age of 29 in 2017.  She began her career with the Mississippi Export Railroad in customer service.

Caren Kraska became the President of Arkansas & Missouri Railroad upon the unceremonious passing of her beloved partner and husband Reilly McCarren when he was just 58. Praised as one of the most successful and creative railroad operators in America, Reilly told Caren that she could sell the railroad or become the railroad’s leader. She chose to be the leader, and sharing an intellectual curiosity and an accomplished pedigree as an MIT graduate herself, Caren has been “full steam ahead” ever since, bringing her moxie and entrepreneurial spirit to the railroad and making it a critical partner in Arkansas & Missouri for businesses needing to move their products across the heartland.

Women are employed in other high-level railroad executive positions, with many women leading railroad departments. Genesee & Wyoming Inc. (G&W), a nearly 125-year-old short line railroad holding company, is led by General Counsel Allison Fergus. Westchester has an all-female team of underwriters that collaborates closely with Allison’s legal team today, as the railroad’s excess and surplus lines carrier for commercial property and casualty insurance with Westchester, a Chubb Company.

Like all short line railroads, G&W’s 115 freight railroads are a crucial link in the country’s supply chain, connecting more than 3,000 customers with the larger freight rail network. Although the short lines are individually smaller than their Class I railroad counterparts, the G&W short lines operate approximately 50,000 miles of track, nearly 30% of the national rail network.

Historically, men almost exclusively were engaged in the arduous labors of building the first transcontinental railroad in the 1860s, moving earth, digging tunnels and laying rails on rugged landscapes. Often using explosives, the risk of an avalanche was a constant threat. Women were on the scene as nurses, hired to attend to injured workers, something we learned from a virtual presentation given by Ms. Chris Enss, author of the book, Iron Women: The Ladies Who Helped Build the Railroad.

It wasn’t until the 1870s that women became more involved in actual railroading, working as telegraph operators, as Chris commented during her presentation to Westchester employees, brokers and policyholders in March 2020 during Women’s History Month. She also cited several female inventors during that decade. Eliza Murfey, for example, created a device in 1872 that improved how railcar wheel bearings aligned with the axles. Seven years later, Mary Elizabeth Watson developed a system that deflected emissions from locomotive smokestacks. Nevertheless, it wasn’t until the 1970s when the first female railroad engineer was hired.

In the industry today, women perform an increasing variety of roles. A 2020 report from Oliver Wyman found that women tend to operate in more collaborative, inclusive and integrative ways. As more women take on leadership positions across the industry, the report states, their diverse perspectives will help deliver the innovative, “outside-the-box solutions” that the railroad industry needs to address declining freight traffic market share and optimize costs. “The diversity of the talent sitting at the table [is] something we need now more than ever.”

Our work with G&W illustrates the success that can be attained by collaborating inclusively with other women on innovative “outside-the-box” solutions. Success is not borne overnight; the strong ties we share today as partners were years in the making.

A Blossoming Relationship

G&W owns mostly small, locally run and operated Class II and Class III short line and regional railroads in the U.S. and Canada, along with operations in the UK and Europe. Founded in 1899 as the Genesee & Wyoming Railroad, the company at the outset operated a single-track line serving a single customer, a salt mine in Retsof, a tiny hamlet in eastern New York State serving the counties of Genesee and Wyoming.

Westchester has had a very strong Excess Casualty underwriting relationship with G&W since 2013 when our railroad insurance department was created to broaden its North American footprint into the short line and regional railroad liability insurance space.

In 2016, Allison was deeply involved in G&W’s planned acquisition of Providence & Worcester Railroad (P&W), a Class II railroad operating in Rhode Island, Massachusetts and Connecticut. She was performing the customary due diligence into the then-172 year-old railroad, which operated with a different risk profile than G&W and in particular, analyzing the railroad’s incurred loss experience. G&W learned during the due diligence that Westchester was already the railroad liability insurer for P&W. This gave Allison and her team a sense of comfort, because they knew that Westchester would be able to provide accurate and up-to-date risk information as part of the companies’ due diligence process. Westchester, in fact, did provide a thorough assessment on all the open claims as part of the due diligence and the acquisition. Allison and our team were put through our paces that summer when a tough FELA claim occurred as the acquisition was being finalized. Allison and her in-house claims department sprang into action and worked hand in hand with Westchester claims to reach a successful resolution on the difficult claim. We recall Allison complementing our complex-claims examiner Tom Hubany and that she was pleasantly surprised at how deftly and proactively the claim was managed and that we should consider that high praise coming from her, as her team had not always had such results with other railroad liability insurers. It was then that a respectful and mutual admiration of each other’s ability to “TCB”—take care of business—came to life.

Gradually, our all-female team of underwriters became more acquainted with Allison’s claims team. We clicked as a group, often sharing war stories and gaining valuable insights from one another on various claims calls, in no small part due to the fact we were all women in an industry in which men held the lion’s share of jobs and authority. Allison was a rarity when she became General Counsel of G&W 18 years ago; she was the sole female member of the executive team. Her moxie and shrewd legal strategies were a force to be reckoned within the railroad industry, and the team found her fascinating to listen to and inevitably would, following every conversation, learn something new about our railroad insuring craft.

Other factors in what we believe drove our successful partnership include the team’s emphasis on white glove customer service, mutual respect and an innovative, collaborative and integrated management approach to solving problems. Our shared values, similar work ethic and aligned execution attributes were of great importance to Allison and her management team during the pandemic, when G&W and its primary insurer ended a longstanding business relationship. She reached out to Westchester (as G&W’s lead excess liability insurer) to inquire if we could reevaluate the company’s entire domestic and foreign casualty insurance program to suggest improvements.

The team rose to the occasion, soliciting assistance from Chubb Global Casualty colleagues specializing in diverse classes of insurance business such as workers compensation, general liability, automobile liability and the Foreign Casualty insurance department, to assist her team’s Global Casualty needs. Ultimately, Westchester’s support during the period as G&W’s lead Excess Liability insurer paved the way to an insurance partnership that provides wide-ranging excess liability coverages for G&W’s 115 short line railroads.

Branding Our Value

Right around the same time in March of 2020, author Chris Enss gave Westchester employees, brokers and policyholders her book presentation through an online session. Having visited a few short line railroads in our work, the team had already immersed themselves in the industry of today, and we thought it would be a good diversion for them during the pandemic for Chris to introduce them to the industry of the past, especially the largely unknown roles that women played. Chris did so with great aplomb, even adorning herself in a period-specific costume from the 1860s.

Some of the interesting facts we learned during her captivating presentation was that women made and repaired the textiles used in Pullman sleeping cars in the late 19^th century, from the upholstery in the seats to the carpets and even the bed mattresses. Some women changed the course of the railroad industry. During World War I, to ensure food could be safely transported to American troops abroad, Mary Engle Pennington, an engineering genius, designed the first properly insulated refrigerated railcars. Mary was later profiled in an article in The New Yorker magazine titled “Ice Woman.”

Westchester purchased copies of Chris’s meticulously researched book and then passed them on to our insurance brokers and customers. One customer subsequently called the team the “Iron Women of Westchester.” We loved it. The name stuck out of a deep sense of pride in our accomplishments as a tightly knit group of railroad insurance underwriters. We bring to the table a formidable team of women across different age groups and various ethnicities who love everything about railroading and insurance.

Our involvement with Allison and her team suggests the railroad industry will benefit from more women and historically underrepresented talent to comprehensively assess business risks and generate more profitable revenue. With global freight and passenger rail activity expected to double by 2050, diverse thinking and collaborative ideas are needed to meet the industry’s increasing demands for innovation.

As an organization, we are continuing to strengthen and elevate the voice of women with the creation of the Westchester Women’s Advisory Council, which represents 20% of all Westchester senior leadership. This National Council of 11 Westchester female employees has implemented initiatives to help with hiring, retention, promotion, mentoring, networking and education. We’ve seen firsthand how their dedication has increased overall employee satisfaction, strengthened our culture and led to a more diversified workforce. During the first year of this program, half of the promotions have gone to women, and we have actively recruited young women, who composed nearly two-thirds of our 2023 intern class.

Our message to all women, but particularly young women looking for meaningful and fulfilling work at the outset of their careers, is that railroads and insurance, industries that fuel the economy and grease the wheels of commerce, need your unique perspectives and can-do attitudes to deliver collaborative, innovative and outside-the-box solutions. 

Catherine “Cate” Whiddon has served the insurance and risk management needs of the railroad industry for more than 30 years and today is Senior Vice President and Railroad Practice Leader at Westchester, the excess and surplus specialty insurance group within Chubb, the world’s largest publicly traded property and casualty insurer.