Jennifer Halloran, CMO, Head of Marketing & Brand, MassMutual

Recap

The FCS community was treated to a thoughtful and inspiring conversation during our June 25 Virtual Spotlight event, featuring Jennifer Halloran, CMO and Head of Marketing and Brand at MassMutual. Interviewed by Lisa Barnhart of The Wall Street Journal | Barron’s Group, Jennifer reflected on her nearly 10-year journey at MassMutual, sharing candid insights about leadership, reinvention, and what’s next as she prepares for a professional transition.

The conversation opened with a personal moment—Jennifer’s recent two-week trip to Tuscany, her first extended vacation in a long career. It was there, under the Tuscan sun and with a camera in hand at sunrise, that she began to gain new perspective on work-life balance, intentionality, and the value of stillness. That time away helped crystallize her decision to step down from MassMutual, as she realized her team was well-positioned to thrive without her and that it was time to open the door to new possibilities, both for herself and her colleagues.

Jennifer spoke about the importance of succession planning and knowing when to step aside so others can grow. Her decision wasn’t driven by dissatisfaction but by clarity: “They can do this without me,” she said, adding that her team is ready for bigger opportunities. Her next chapter will be shaped by reflection and exploration—leaning into conversations with mentors, peers, and partners to determine how she can apply her passion in new ways.

Throughout the discussion, Jennifer drew from her diverse experience across agency and corporate roles, offering valuable takeaways on leadership and team-building. She described how her early agency years taught her the importance of collaboration over titles and instilled a mindset that every colleague—internal or external—should be treated like a client. That belief carried into her work at MassMutual, where she leads a 200-person marketing team and has championed a culture of trust, empowerment, and shared purpose.

When asked how she transformed a fragmented department into a unified, high-performing team, Jennifer credited her “go with your gut” mentality and commitment to making decisions quickly, even under pressure. She described the importance of building “centers of excellence” within the organization and ensuring those centers not only operate at a high level but also respect and listen to each other. “I didn’t call them centers of mediocrity,” she joked. The goal, she said, was never perfection but cohesion and progress—creating an environment where strong voices could collaborate rather than compete.

Jennifer also emphasized the role of mentorship and self-advocacy, especially for those early in their careers. She encouraged young professionals to speak up, own their ambitions, and embrace the process of figuring out what they don’t want as much as what they do. Her team-first philosophy, often reflected in MassMutual’s campaign work, is rooted in the belief that “you can’t do it alone.” Whether working with in-house colleagues or agency partners, she insists on honest dialogue, mutual accountability, and respect.

One of her proudest achievements was leading a major brand refresh for MassMutual—a 165-year-old financial institution with limited resources and a complex distribution model. Jennifer discussed the internal education process required to build belief in the brand’s potential, especially among the firm’s vast advisor network. By focusing on brand equity as a tool that empowers those advisors at the point of sale, she helped shift mindsets and strengthen adoption across the field. Seeing local advisors proudly adapt and personalize the brand campaign was, she said, one of the most gratifying outcomes of the entire effort.

As the conversation turned to the future of marketing, Jennifer stressed the importance of staying curious and connected. She cited her reliance on peer networks, agency partners, and organizations like the FCS to stay ahead of emerging trends—from AI to cultural shifts to media innovation. She described her team’s practice of regularly reviewing the “four Cs” (culture, customer, company, competitors) as a strategic exercise that keeps them grounded in what’s changing—and what still matters.

Looking ahead, Jennifer is drawn to areas where she can combine her marketing experience with broader impact—especially in sponsorship, women’s sports, and customer engagement. She’s also interested in political and economic issues, noting her background in economics and political science and her morning routine of consuming Bloomberg podcasts. But most of all, she’s excited to reclaim time—to be present with family, give back to the community, and reflect on where she can add the most value.

The FCS extends our thanks to Jennifer for her transparency and wisdom, and to Lisa for guiding the conversation with such warmth and insight. We look forward to seeing what comes next for Jennifer—and how her next chapter will continue to shape the future of our industry.