By Adam Sylvain

Brooke Bass T’04 has never been someone to back down from a challenge. Joining Plymouth Rock Assurance as COO last year marked the latest in a series of smart bets Bass has made throughout her more than 20-year career as an insurance industry leader.

“Looking back, my journey has been defined by a series of choices to get out in deep water and embrace the unknown,” says Bass. “Those decisions, while somewhat scary in the moment, have always led to personal and professional growth.”

A story that perhaps best illustrates this theme came several years into Bass’s two-decade tenure at Liberty Mutual. She had just returned to work following her second maternity leave—this time, triplets—when Bass walked into a meeting with her boss.

“The first thing she said to me was, ‘The chief actuary wants to hire you. What do you think?’,” recalls Bass. “As a new mom of now four children, it would have been easy to justify staying put and playing it safe, but I trusted the inner voice that told me this was a risk worth taking.”

The decision paid off as Bass rose through the ranks at Liberty Mutual to assume executive leadership roles in both corporate strategy and operations. She says these complementary experiences have made her a more well-rounded leader—skilled at big picture thinking and problem solving but grounded in the day-to-day realities of running a business.

Bass became COO of Plymouth Rock during a time of rapid change across the insurance industry. This includes heightened customer expectations, which are increasingly being shaped by interactions with companies across a wide range of industries.

“Our customers are used to clicking a few buttons and receiving the goods they ordered overnight,” says Bass. “Even if what we provide is not close to the same product or service, that expectation is transferred onto us.”

Managing these expectations is a challenge in a heavily regulated industry that has historically made moving fast difficult. Nevertheless, Bass says the onus is on operators to design processes and leverage technology in ways that drive efficiency.

“Whether we are talking about process changes, hiring different types of talent, or leveraging agentic AI and other new technologies, it’s all about being agile,” she says. “The environment we’re operating in demands that we’re constantly improving and offering new products and services at a faster rate than we ever have before.”

Acknowledging the near-constant pressure to do more, and do it faster, Bass believes operational excellence is about more than margins and outputs. The right talent surrounded by good processes and tools can produce short-term gains, she says, but the kind of sustained, long-term success most businesses are after demands more than that. It requires visionary leadership, a framework to empower decision-making across the organization, and a culture of shared accountability and trust.

“You can luck into a good outcome, and you can follow a good process and arrive at a bad outcome,” says Bass. “What sets organizations apart, in the long term, is having alignment on a shared vision and a culture in which everyone feels trusted and supported in the decisions they are making every day.”

Looking back on her career to this point, Bass says the path she followed would have been hard to fathom when she joined Liberty Mutual in 2004. At that time, it was rare to see women in senior leadership roles at top insurance companies. Being part of the evolution that has since taken place—with two of the leading U.S. providers now led by female CEOs—has been a highlight of Bass’s career. Today, she finds even more fulfillment in helping high-potential female leaders find their footing in the industry.

“The first thing I try to emphasize is the importance of having a confident mindset that you deserve to be in the room,” she says. “If you have a thought, a perspective, an opinion, you need to speak up. The organization will be better for it.”

Second, Bass stresses the importance of being authentic. The temptation to fit a mold or mimic the dominant culture in an organization can be strong, and it is something Bass admits struggling with herself at different points in her career.

“You get in the trap of seeing someone you admire and thinking, ‘Oh, that person behaves this way and they’ve had success. Let me try that,’” explains Bass. “But if that’s not authentic to who I am, I’ll end up stumbling over myself, and I won’t be maximizing my talents and capabilities in ways that help me be successful.”

Finally, as both an accomplished business leader and mother of four children, Bass has experienced firsthand the need for a strong network of supporters and advocates.

“Despite what people may claim, nobody maximizes their potential fully on their own, or in a vacuum,” she says. “It takes a village and I’ve tried to learn as much as I can from other successful women who blazed a path before me.”