Pioneering CAS Fellows: Linda Shepherd and Ollie Sherman Reflect on their Careers

In ways small and large, Linda Shepherd and Ollie Sherman have forged a path for others looking for fulfilling actuarial careers.

November 2020 marked a milestone for actuaries as Linda Shepherd, who in 1988 became the first Black woman to earn a CAS Fellowship, officially retired.

Four years earlier, in 1984, Ollie Sherman became the first Black actuary to qualify for Fellowship. (Sherman retired in 2010). How did these pioneers achieve their historic firsts? Although they followed very different career paths, both point to the value of mentors, the importance of a community of colleagues, and an abiding interest in the problem-solving work of the profession itself.

Two careers in photos (top to bottom): Linda Shepherd, FCAS, (third from left) with other inductees of the first Copiague High School Hall of Achievement in 1997. The man behind her to the right is the actor Kene Holiday. Shepherd with a plaque given to her by colleagues celebrating her earning the CAS Fellowship in 1988. Speakers gather after a session honoring leaders of the International Association of Black Actuaries (IABA) in 2017. Pictured left to right are Jeff Johnson, FSA; Stafford Thompson Jr.; Tenesia McGruder, FSA; Ollie Sherman, FCAS; and Chris Cooper, the session’s master of ceremony. Sherman speaks during the session honoring IABA leaders at the organization’s annual meeting in 2017. Photos courtesy of Linda Shepherd and the International Association of Black Actuaries.

Shepherd thinks her introduction to the job was unique — especially for the 1970s. “I’ve told my story for the last 40 years,” she says, “and no one has had a similar story until recently.” Shepherd first heard about the career from her high school guidance counselor, who happened to have a neighbor who worked as an actuary. The counselor even arranged for Shepherd to visit the neighbor’s office and take a tour.

With her mother along to supervise, the high school junior took the Long Island Railroad into Manhattan and entered the doors of George B. Buck Consulting Actuaries in Penn Plaza. “It was absolutely an adventure,” she recalls. Then the truly unexpected happened. “They asked if I’d be interested in a summer job. And I was laughing because I was thinking to myself, ‘Is the Pope Catholic?’”

A guide and inspiration: Linda Shepherd and one of her mentors, Robert Randall, FSA, the first Black Fellow of the Society of Actuaries, at Shepherd’s CAS Fellowship party in Hartford, Connecticut, in 1988. Bob Randall died in 2012.

On the spot, Shepherd took a paper-and-pencil test in which she computed a retirement benefit. She got the correct answer and was hired for a summer internship as a benefit calculation clerk.

Sold on the job, Shepherd applied to the University of Pennsylvania’s Wharton School so she could major in actuarial science. After her junior year at Wharton, a summer internship at Philadelphia’s General Accident Group in property-casualty insurance, turned out to be the key to her career. “That’s when I decided I was interested in property and casualty,” Shepherd says. After graduation, she landed a job at Aetna in Hartford, Connecticut. She describes the world of property-casualty insurance in 1981 as a little like the Wild West. “There weren’t that many P&C actuaries,” she explains, “because a lot of the work until then had been done by a rating bureau, the Insurance Services Office (ISO).”

On the spot, Shepherd took a paper-and-pencil test in which she computed a retirement benefit. She got the correct answer and was hired for a summer internship as a benefit calculation clerk.


Due to the changing times, Shepherd got started with a group of other newbies. “When I first got into my program on the P&C side,” she remembers, “there were six of us hired directly out of school. Only two of us had one exam, and everybody else had no exams. Life was established, but it intrigued me that on the P&C side, it was just coming up with new processes and trying to figure it out. On top of that, we didn’t have personal computers back then! When the company got the first personal computers, we had to sign up for an hour of time to use them.” She fondly remembers her first spreadsheet program, the venerable Lotus 1-2-3.

Shepherd discovered that Hartford was not a diverse city. But within Aetna, she soon found a community of other African Americans. “Within a couple of years after I started,” she says, “Aetna had a luncheon for all of the African American actuaries that had been hired by either the life or the casualty side. There were 13 or 14 people who were at that luncheon in the mid-1980s. I thought that was pretty cool that they were very tuned into diversity and wanted to make sure that the program was strong with African Americans. It was a neat thing to be able to see so many African Americans like myself studying to become actuaries.”

At the lunch, Shepherd crossed paths with Ollie Sherman, who started working at Travelers in Hartford in 1975. “I was surprised by the number of folks in the Aetna program who looked like me,” Sherman says. “They had organized a network to provide study assistance and moral support to students in their exam efforts.”

Unlike Linda Shepherd, Ollie Sherman became an actuary almost by accident. “I’d never even heard of an actuary until I was out in the job market,” he says. At the University of Virginia, Sherman started out as an engineering student. “Then they opened a program in applied math and computer science during my senior year,” he says, “so I moved over to that. I was one of the first majors. I liked the practical applications of mathematics and the problem solving and the logic.”

“Aetna had a luncheon for all of the African American actuaries that had been hired … There were 13 or 14 people who were at that luncheon in the mid-1980s. I thought that was pretty cool that they were very tuned into diversity …
— Linda Shepherd


Sherman took his applied math degree to the Federal Reserve Bank of Richmond, Virginia, but found the work too bureaucratic. He came across one vital clue to his future there, however, when he learned the actuarial method of calculating rebates for customers who paid off loans early. He searched for more information about actuaries, found some recruiting materials from Travelers Insurance and moved to Hartford in 1975 to start work there.

Sherman was in for a shock. “When I joined the actuarial profession,” he recalls, “I was pretty naive and pretty cocky. I thought, ‘the exams gotta be pretty easy. I’ll knock them out in no time and then I’ll decide what I really want to do.’” Not only did the exams prove much tougher than Sherman expected, but he was also surprised by “the quality of people that I was dealing with and the kinds of issues that they were dealing with. I found them pretty interesting.”

A big mahalo for a rewarding career: Linda Shepherd at the 2019 CAS Annual Meeting in Hawaii.

Sherman kept powering through the exams, but the last one was particularly hard and took three years to complete. Says Sherman, “I thought, if I don’t do it this time, I really need to reconsider what I’m going to do.” But eight years after he started, in 1984, Sherman became a CAS Fellow.

“I was proud of that,” he says, “and my parents were proud. That was one of the driving forces, trying to make my parents proud of me. Neither one of them had an opportunity to go to college. My older brother and I were the first in our family to attend college.”

Four years later, Linda Shepherd also became a CAS Fellow. “There was this nice-sized pool of African Americans actuaries in Hartford at the time,” she remembers, “and they surprised me with a Fellowship party.” Some 20 guests celebrated her accomplishment with dinner and cake, and a must-have accessory for 1988: a briefcase.

For Ollie Sherman, becoming the first African American FCAS wasn’t easy. “I don’t think, when I was hired at Travelers, that they ever expected me to complete the exams and to go all the way to the Fellowship. At that time, there weren’t any successful minority candidates in the casualty actuarial profession,” he says. “One of the first guys I met there, Jim Walker, was kind of my role model and mentor. He was an African American gentleman. He had started out in the actuarial profession, and he felt like they never gave him the opportunity to pursue the exams. So one of the driving factors for me was to finish what he had started. Whenever I got discouraged or feeling down about the exams, I’d speak with him and he’d encourage me to keep going.”

Linda Shepherd found the support of those who broke barriers before her was invaluable, including Bob Randall, who became the first Black Fellow of the Society of Actuaries in 1952. (Randall, a Yale graduate, served in World War II with the Tuskegee Airmen. Told he was too tall to be a pilot, he worked as a mechanic with the unit. He later became the first Black president of a national insurance company.) “He was an inspiration to almost all of us who were able to meet him at that time,” Shepherd says. “He came to a lot of our functions. His attitude was, you’re an actuary and I’m supporting you.” Randall even made it to Shepherd’s Fellowship party.

“Jim Walker … had started out in the actuarial profession, and he felt like they never gave him the opportunity to pursue the exams. So one of the driving factors for me was to finish what he had started.”
—Ollie Sherman


Shepherd also credits other Black women pioneers, including Daisy McFarlane Coke, the first African American woman to become a Fellow of the Institute of Actuaries in 1970, and Marsha Bera-Morris, the first African American woman to become a Fellow of the Society of Actuaries in 1978.

As their careers began to flourish, both Shepherd and Sherman joined the fledgling International Association of Black Actuaries (IABA), which was launched in 1992. Just three years earlier, industry analysts had estimated that out of the nation’s 11,500 actuaries, only some 50 were Black. Says Sherman, “We got together as a community to support each other and to encourage other people to take on the challenge of the exams.” For Sherman, that sense of community was an antidote to the isolation he felt when he first started taking exams. “I was kind of struggling with it alone,” he says. “You don’t see people who look like you and the majority candidates don’t fully appreciate all of the things that happen with the minority applicants.”

Ushering in a new generation of actuaries: From left to right, Ollie Sherman, Tenesia McGruder, FSA, and Marsha Bera-Morris, FSA, at the IABA Annual Meeting in 2017. Bera-Morris became a Fellow of the Society of Actuaries in 1978, the first Black woman to do so.

Linda Shepherd found that joining IABA let her help others discover a fulfilling career. “I knew there were lots of other people like me — a little girl who loved math — and really wanted to make sure I had a very nice career. I always thought that was my calling: to reach back and try to explain to people what I do and why this is a great career. A lot of other people thought the same way, and that’s why IABA was formed.”

Shepherd says that in the early days of the IABA, “It was even hard to find where the African American actuaries were working. It started really slow, but then we really picked up steam.” Shepherd served as president from 1996 to 1998. She credits Stafford Thomson, who became IABA president in 2002, with taking the organization to the next level. “Thomson was the first person to say, ‘Let’s work with corporations who want to improve the number of African Americans they have and see if we could get funding from them.’ And we could have scholarships and other types of programs,” she says. “It got much bigger to do the work that we needed to do — to find talented African Americans who wanted to be actuaries.”

Shepherd went out to look for the next generation of Black actuaries herself, under the auspices of the IABA and the Joint Committee for Inclusion, Equity and Diversity, a collaboration of CAS and the Society of Actuaries. “I spent a lot of time, especially as a newly minted Fellow, going into places like Howard University, Florida A&M University, and then more recently, Morgan State University — schools that have actuarial science programs,” she says.

Ollie Sherman got involved with the same recruiting program and worked with Howard University’s summer actuarial program. “Howard had this program where they’d bring in high school juniors to introduce them to the actuarial program,” Sherman says. “We set up an advisory board for the actuarial program at Howard that was supported by the industry, and I was initially Travelers’ representative on that board, and then I became the Tillinghast representative.”

One of Sherman’s goals was seeing Black students complete more exams before graduation. “One of the things that I found out was that a lot of the majority folks came out of school with three or four exams, so they’re at an advantage to begin with,” he says. “We’re trying to better promote the profession in the minority community, so they can take advantage of those opportunities to look at it earlier and start to develop some background that might help them.”

After becoming a CAS Fellow, Linda Shepherd went on to a long career in property-casualty insurance, eventually taking management positions at Prudential in New Jersey, Safeco in Seattle and Fireman’s Fund Insurance in California. Ollie Sherman moved to Towers Perrin and spent more than 25 years as a consultant and practice manager for the company’s property and casualty division. Both have served on the board of the IABA, which has now grown to over a thousand members. And both believe that African Americans have made inroads in the actuarial world since they first started. “I think that the face of the industry has changed pretty dramatically over the last decade,” says Sherman. “It wasn’t fast progress, but it certainly has accelerated over the last decade.”

Sherman remains hopeful about the future. “One of the things that’s been really rewarding for me is being involved with IABA and seeing all the young people coming through who are starting to pursue the actuarial profession,” he says. “It’s pretty encouraging to see these young folks, who are willing to work hard for themselves, as well as be involved to help others.”

Dispensing wisdom: Sherman at the 2017 IABA Annual Meeting.

Looking back on her career, Shepherd says, “I’ve never had any regrets about choosing this career. It was very rewarding for me, because it gave me the opportunity to use the skills that I had in math, with loving computers, and loving bringing other actuaries on.”

She notes that finding out about the career is far easier now, compared to 40 years ago. “Today, if you want to know what to do with your math degree, you can just jump online and get all sorts of career questionnaires and things that could guide you.” Shepherd recently took one of the career quizzes for fun and found out that she should become … an actuary. “If I’d had this questionnaire way back when,” she says, “it would have said the same thing.”