For much of its recent history, the insurance industry has taken pride in its stability and conservative culture. That current caution is consistent with the core mission of managing and transferring risk. But starting with the dot-com era and accelerating with digital technologies, insurers began to feel real pressure to rethink how they operated and how they engaged with customers. It became clear that the traditional model, largely unchanged for centuries, was ripe for disruption.
From large multinational insurers to federated companies with local market structures, we have collaborated on custom-built programs that not only respond to immediate challenges but also create lasting impact across the enterprise. What has struck me most over the years is how varied the needs are—and yet how consistent the underlying themes become. Whether the issue is digital transformation, cultural alignment, or the responsible adoption of artificial intelligence, the core challenge is preparing leaders to think differently, to innovate, and to carry change forward in their organizations.
Fostering a growth mindset at The Hanover Insurance Group
When we worked with The Hanover—a U.S. property and casualty insurer—the brief was clear: invest in leaders’ innovation skills and equip them to guide dynamic, agile teams. Together with MIT faculty, we developed a focused, two-day on-campus experience anchored in the Innovator’s DNA framework, co-created by MIT’s Hal Gregersen and delivered, in this case, by Dr. Phil Budden, which we then incorporated into applied project work. Each leader selected a business project, tested new practices, and reported back—creating visible momentum and, in several cases, direct ROI.
What mattered most was what happened afterward. The Hanover embedded a growth mindset into its values and leadership capabilities, and supported leaders in modeling and embedding innovation into their teams. As Emily Robbins, AVP, Learning and Development Business Operations at The Hanover, put it: “Partnering with [MIT] Sloan provides long-lasting results for your leaders and the business. We found immense value through partnering upfront to share our strategy, and together we then customized the program to our unique needs.” And over time: “Growth mindset and innovation continue to be part of our culture and values.”
This engagement became an early template for how an innovation program—delivered with rigor and tied to real work—can shift language, norms, and outcomes across an insurer.
Enabling strategic alignment at a leading Northern European insurer
Another major insurer—a legacy organization with deep roots in Northern Europe—sought to unify its leadership culture following years of growth through acquisition. With geographic offices and business lines operating semi-independently, executives realized they needed a common framework for data strategy, innovation, and leadership.
Our two-tier program began with the C-suite, who explored future pathways for strategy based on cutting-edge research and then directly applied those concepts to their own company context. From there, the learning cascaded to more than 300 managers. Through strategy-focused sessions, executives applied frameworks to discover the opportunities available through innovation-led growth. In the cascading program, managers considered how to scale learning across the organization.
What made the program distinctive was the integration of alumni from the executive cohort back into subsequent modules. Senior leaders who had already applied the learning shared their experiences, challenges, and progress, creating a sense of continuity and authenticity that accelerated adoption across teams.
The result was not only a shift in mindset but also the operational groundwork for unified data lakes, common standards, and cross-company knowledge sharing. In a federated organization, this alignment marked a significant step toward capturing the efficiencies of technology while sustaining local customer focus.
Driving cultural transformation at Generali
Another example comes from Generali, one of the world’s largest insurance and asset management providers. Established in 1831 and headquartered in Italy, Generali is both deeply rooted and globally ambitious. Facing industry disruptions and executing on its “Lifetime Partner 24” strategic plan, Generali needed its leaders to embrace cultural transformation while staying true to its commitment to customers and sustainability.
Generali selected MIT Sloan Executive Education to co-design “Inspired Minds, Sustainable Futures,” a program aimed at inspiring its senior executives worldwide. The program faculty director, senior lecturer, and research scientist Renée Gosline, and I travelled to the company’s headquarters in Milan for a deep dive into Generali’s culture and strategic priorities before shaping the program. Over three successive cohorts, we worked with CEO-level leaders, Group and local function heads, and the Group Management Committee, tailoring the curriculum to each audience.
The program combined classroom sessions on artificial intelligence, climate change, diversity and inclusion, organizational behavior, and systems thinking with immersive visits to MIT labs and startups. Faculty emphasized rigor, relevance, and application, asking executives to “roll up their sleeves” and problem-solve using the new frameworks.
The results were immediate: greater openness, stronger energy, and a new sense of alignment across leadership. As Generali’s Group CEO Philippe Donnet reflected, “The program truly exceeded our expectations. More than a learning experience, it turned out to be an amazing journey both on a personal level and collectively, as it allowed us to broaden our views, challenge our decision-making processes, gain exposure to innovative ideas, and ultimately develop key skills and a different mindset that will help us leave an even greater mark as we keep steering Generali forward.”
The Generali "Inspired Minds, Sustainable Futures" has won Gold for Best Executive Development Program at the 2025 Brandon Hall Group HCM Excellence Awards, which honor leading organizations worldwide that have designed and implemented programs with measurable impact, setting new benchmarks in Human Capital Management.
Read more: learn about the Generali program experience and outcomes.
Exploring AI with a leading European insurer
Most recently, MIT Sloan collaborated with another leading European insurer on a custom program that reflected one of the industry’s most urgent frontiers: artificial intelligence. This was one of the first custom executive programs co-designed with the MIT Schwarzman College of Computing, highlighting the Institute’s cross-disciplinary strength.
A faculty leadership team representing both computer science (Schwarzman College) and organizational change (MIT Sloan) introduced senior executives to the fundamentals of AI, generative models, ethical and trust considerations, workforce implications, and the organizational risks and opportunities inherent in deploying AI at scale. Sessions ranged from technical explorations of data scaling and machine learning to leadership-oriented discussions on governance, organizational culture, and anticipating unintended consequences. Stephanie Woerner’s contribution on digital transformation in insurance, including industry examples, resonated strongly with participants.
For executives in a highly regulated and risk-averse industry, this program provided a critical, evidence-based foundation for AI adoption—anchored in MIT’s thought leadership and its ability to convene expertise across disciplines.
Building capabilities that shape insurance innovation
After our work with The Hanover, the insurance ratings agency AM Best invited MIT Sloan Senior Lecturer and a key program faculty member, Dr. Phil Budden, to contribute expertise on how to assess insurers’ innovation efforts. AM Best published a 2020 innovation-rating methodology that remains in use today. The signal to the market is clear: leadership, culture, and innovation capability now factor into how insurers are evaluated, reinforcing why disciplined, context-specific executive development matters for the business—and not just for talent.
For insurance companies—or their competitors—rated by AM Best, this methodology for scoring and assessing innovation, informed by MIT’s research, is a handbook for success in such efforts. Across these diverse engagements, several themes emerge. Legacy insurers must adapt to a data-driven and AI-enabled future while maintaining the trust and stability at the core of their mission. Cultural alignment, innovation mindsets, and future-ready leadership are no longer optional, they are competitive differentiators.
Guiding transformation in the financial services sector
MIT Sloan Executive Education is uniquely positioned to guide this transformation not only in the insurance business, but also in banking, asset management and other financial services firms. By bringing together world-class research, cross-disciplinary faculty, and contextualized program design, we help companies align leadership, unlock innovation, and prepare for an uncertain future.
Connect with us: if your organization is facing a transformational challenge, we are here to help.