The corporate lawyer-turned-executive grew up in Beaumont, Texas, just a short drive from a town called Vidor — a former white supremacist stronghold known as a sundown town. “If you were Black, you knew not to be caught in that town after dark. I was acutely aware of what that town represented, particularly as it relates to Black people. My personal experiences, as well as those of my family and friends, taught me that there were, and still are, people in this country and around the world who view Black people as second class citizens, as inferior, unworthy and less than,” Flanagan says.
As a longtime corporate lawyer and chief of staff to the CEO at Massachusetts Mutual Life Insurance Company (MassMutual), Flanagan exists in professional spaces that directly compete with racist narratives of Black Americans’ worth and value. She is both a staunch advocate for racial justice and an active member of the business community when it comes to diversity and inclusion (D&I).
This year, Flanagan has made the decision to step away from her central role at MassMutual to serve as the COO of CEO Action for Racial Equity, a fellowship launched in October to galvanize talent and resources from American companies and organizations to work together and address societal systematic racism. The fellowship was launched by CEO Action for Diversity & Inclusion (CEO Action) — a coalition of more than 1,400 CEOs and presidents, representing 13 million employees, who have signed a pledge to take action to advance diversity and inclusion in the workplace.
CEO Action for Racial Equality offers an opportunity for CEO Action signatories to directly contribute to changing public policy at the federal, state and local level. Companies who participate in CEO Action for Racial Equity must contribute at least one full-time employee from their staff to step away from their day job for one to two years to focus solely on responsibilities for the fellowship. Pooling talent from passionate members of America’s corporate workforce — lawyers, data scientists, human resources specialists, D&I officers — the fellowship’s objective is to find new frameworks for public policy-making that advance racial equity. By upturning discriminatory systems and advocating anti-discriminatory strategies, CEO Action for Racial Equity will work to help advance Black Americans access to economic resources and services, among other things. Through a lens of social justice, the fellowship aims to focus on four foundational elements of societal well-being: education, healthcare, public safety and economic empowerment.
MassMutual CEO Roger Crandall was one of the first 150 CEOs who signed the CEO Action pledge back in 2017 and is now serving as a member of the fellowship’s 20-person governing committee. In addition to Crandall and Flanagan’s participation, five other MassMutual employees will be stepping away from their day jobs for the next two years to serve as fellows for CEO Action for Racial Equity.
“We don’t want to just talk the talk, we want to walk the walk,” Flanagan says. “I think the need for change is great, but more importantly, it’s urgent. We need to do more, now.”
Mobilizing more than 250 professionals from more than 100 cross-industry organizations, the CEO Action for Racial Equity fellowship is one of the country’s largest business efforts aimed at advancing racial equity through public policy. Its mission is to identify, develop and promote scalable and sustainable public policies and corporate engagement strategies that address systemic racism and social injustice, and improve societal well-being.
Personal experiences influencing professional direction
Flanagan is uniquely qualified for her new role at the fellowship: Her personal and professional journeys have never existed separately from each other. The observations that she made about the disenfranchisement of Black Americans in her family did not conflict with the lack of representation and inclusion she experienced in law offices.
“My grandfather and other Black veterans returning from World War II were denied benefits that would have enabled them to receive loans, attend college, start a business or purchase a home,” Flanagan says. “These resources enabled their white counterparts to set off on a path of prosperity and build generational wealth for their families.”
Flanagan set off on her own path to build wealth for her family when she became a lawyer. She started her career in New York City as a tax attorney, where she started initially as a tax consultant to numerous corporations before moving to high-revenue law firms where she ended up focusing most of her career in the areas of executive compensation and employee benefits.
“I enjoyed practicing law, but being the only Black female at a couple of my law firms was very lonely and very isolating,” Flanagan says. “You feel like you’re a woman on an island. There is no one there who looks like you. You’re not given the plum assignments, you’re placed on matters that may not be a strategic priority for the law firm and you find yourself just swimming along, knowing that if you had a mentor, it could be a lot better.”
When she eventually found her footing — making partner at a multinational law firm — Flanagan realized that she was searching for something else. In 2013, she left her firm for corporate America, specifically an in-house role at MassMutual, after meeting the company’s then general counsel, a white man who was an active champion of diversity and inclusion and would regularly attend conferences for the oldest professional African American bar association.
Flanagan has served as corporate secretary supporting MassMutual’s board of directors, focusing on corporate governance matters and leading a team of tax and benefits lawyers. She has also led diversity and inclusion efforts focused on advancing racial equity across MassMutual, including the company’s Black Strategic Initiative group which assembled this year in the wake of pandemic and social unrest to identify ways to better engage with and support the Black community, both within and outside MassMutual, and develop a long-term action plan to help dismantle racism and create equity.
The mission continues
Flanagan’s journey is now coming full circle. As COO she is responsible for CEO Action for Racial Equity’s day-to-day strategy and operations, but Flanagan says that’s not all she’s responsible for. “It’s about bringing our true, authentic selves to this fellowship. I think it’s important for the fellows to see that there are leaders out there who believe that this is crucial, critical, necessary, and important work.”
The fellows — a broad group of individuals across diverse disciplines and backgrounds — will use a business approach to address societal problems, leveraging data driven, technology-enabled and solution-oriented strategies. “We know that there are about 48 million people Black people in the United States,” Flanagan says. “Everything we do will relate back to that number. So how many Black people are we touching with any of the policy proposals on which we work? We’re also going to be working to identify the root causes of the systemic issues and problems, solutioning around the underlying causes and not just the symptoms.”
The fellowship will also focus on areas that Flanagan calls “positive deviances” – cities or communities that have adopted policies or regulations that enable them to achieve better outcomes than their peers. For example, they will take a solution that may be working in Kalamazoo, Michigan and see if it can be replicated in another city on the other side of the country. “Ultimately, our goal is to enact policies that are scalable, sustainable and impactful,” Flanagan says. “We have a great responsibility to drive social change, and the time is now for corporate America to step up. These are not new issues, but the events of 2020 — the global pandemic, along with the other unjustified killings of African American and Black individuals in their country — have brought them to the forefront.”
Flanagan insists the “why” of CEO Action for Racial Equity is about moving further than giving lip service, writing checks and having open discussions with employees. Instead, it’s about taking action and looking beyond the siloed measures towards long-term scalable solutions that will advance racial societal equity in meaningful ways.
Flanagan’s work with CEO Action for Racial Equity isn’t only focused on benefiting society, it’s also a personal mission to better the world that her young son is growing up in.
“I am a mother of a four-year-old Black son,” Flanagan says. “I owe it to him to do everything that I can to ensure that he grows up in a world where he can just be a child — a carefree child and not lose his innocence in the eyes of others during his youth, because they perceived him to be a threat or thug. I want him to grow up in a world where he will have equal rights, equal opportunities and equal treatment under the law. And more importantly, where he will be judged, not by the color of his skin, but by the content of his character.”
PwC’s new series, Why I Act, produced in association with the CEO Action for Diversity and Inclusion™, highlights the many ways companies and their leaders are affecting change for a more diverse, inclusive and better future. With more than 1,400 CEOs that have taken the pledge, CEO Action is the largest CEO-led business coalition focused on advancing diversity and inclusion in the U.S. To learn more, visit CEOAction.com.
This article was paid for by PwC and co-created by RYOT Studio. HuffPost editorial staff did not participate in the creation of this content.