In 2016, Betsy Ward became the first female chief financial officer at MassMutual (Massachusetts Mutual Life Insurance Company). Looking back at the start of her tenure, she acknowledged that the weight of being the first woman to hold the top financial role at the 173-year-old life insurer likely fueled one of her key initiatives—driving the modernization of the company's financial processes.

Although some employees were initially skeptical, she worked to convince them of the possibility of change. To win support, she organized "field trips" to demonstrate the potential for transformation, and in meetings she did not shy away from emphasizing the necessity of new processes and the potential benefits of reinvesting the savings back into the team.

"I do believe that the huge difference I represented and what I brought to the table made an impact, although I don't want to say a man couldn't have done it," Ward said in an interview last month. She noted, "It was both about how I guided people forward and my proven ability in this area, and the team was willing to follow me."

Ward, now 60, plans to retire at the end of this month after 30 years at the insurance giant headquartered in Springfield, Massachusetts. According to the company's 2023 annual report, the total value of life insurance issued to policyholders last year surpassed $1 trillion for the first time, and total assets grew more than 4% from the prior year to $335 billion. Ward, who is outgoing and unafraid to wear a leather jacket to business meetings full of suits, likes to highlight the people behind the company's numbers: she says MassMutual's oldest policyholder is currently 103 years old.

She believes this is a reasonable time to step down because it gives her successor the opportunity to make their mark in the second phase of the modernization. "We are about to embark on the next phase, so now is a good time to let the incoming person launch and drive these decisions," she said. Mary Jane Fortin, former president and chief commercial officer of Thrivent Financial, will take over as MassMutual's CFO on January 1.

From microfiche to data dashboards

The modernization of the finance team did not happen overnight. In 2016, the year she was appointed CFO, Ward assessed the company's financial processes and found that her department's ways of working were outdated and labor-intensive—her team of about 300 finance staff still stored data on microfiche, and the FP&A team used spreadsheets for forecasting.

But in the early days, her proposed changes shocked some people. At one meeting, she recalled, she first expressed understanding to employees, saying she knew people often said it was hard to work in finance because "your numbers have to be perfect and on time." But she did not stop there. "I said, 'I'm here to tell you that's not enough,'" Ward recalled in the interview. "My point was, 'You need to tell me what the numbers are saying, and if the data comes too late, we can't get the detail we need.'"

When a woman raised her hand and told her there was no time to do more, Ward said she would observe how they spent the end of the quarter to understand the actual workflow. She found they were right: the process was too slow and too manual, and it needed updating through automation so that accountants and others could free up time to analyze data.

By 2018, she began implementing the transformation. The first phase of modernization included introducing robotics, creating data dashboards to provide information, changing how the company stored data (no longer requiring microfiche), migrating some databases, and consolidating some actuarial reserve systems.

A nontraditional path to CFO

Ward did not become CFO through the typical route: she is not a CPA. According to Ward and her LinkedIn profile, she majored in economics and Spanish at the University of Rochester in New York, then followed in her father's footsteps to become an actuary.

Early in her career, she rose through the actuarial program at Aetna Life & Casualty, where she was responsible for describing assets and liabilities so investment managers could invest accordingly. When she realized she and the investment division were effectively "speaking different languages," she asked her boss to learn trading. They then traded corporate bonds in the utilities sector, which gave Ward investment experience and paved the way for her to hold several portfolio manager positions later.

In November 2007, just as the global financial crisis was breaking, she became MassMutual's chief enterprise risk officer. At the time, the insurance industry was debating whether to use mark-to-market accounting or risk management assessments to correctly value assets. "We found we needed both, so you could understand what risk you would face if all depositors left today," she said.

Her predecessor as CFO at MassMutual was Michael Rollings, who left in 2016 to become CFO of U.S. fund manager Vanguard. Because Ward had reported to him, Rollings was able to get to know her and recommend her as a potential successor, and he asked if she was interested in the CFO role. She had doubts. "I said, 'I'm not an accountant,'" she recalled. His response: "Neither am I." She came to understand that at a company like MassMutual, being a strategic CFO involves far more than bookkeeping.

Speaking up

As Ward steps down, female financial leaders have made some progress this year: according to a recent report by leadership consulting firm Russell Reynolds Associates, the number of women appointed as CFOs globally in the first half of this year reached a five-year high. Among them, Google parent Alphabet appointed Eli Lilly veteran Anat Ashkenazi as its new CFO in June. Still, according to executive search firm Crist Kolder Associates' 2024 study, women currently hold only 17.8% of CFO roles at Fortune 500 and S&P 500 companies, down from 18.5% in 2023.

Ward has some advice for those coming after her. She advises young women to be selective when choosing mentors: choose someone above you who is doing what you want to do. She says this is especially difficult for women because they often feel they need to choose a perfect mentor, and sometimes they aim too low when looking for sponsors. "Just pick several," Ward said.

She also noticed that three women in a group can create a certain power. When she became chief risk officer (an executive role), she said she benefited from two other women in meetings—the head of HR and the head of the retirement business area. "There's something magical about three," she said, noting that when there are three, it's not always the same two women teaming up to support each other.

Additionally, in meetings, she learned the importance of holding her ground. She was never intimidated by the financial topics under discussion, but sometimes she had to force herself to speak up—and sometimes even to speak loudly.

"They got louder, so I had to get louder, and I kept talking until I could barely hear myself, but I had to keep going," Ward said. "I had important things they needed to hear. Especially as a risk officer, you have to be able to speak up."