Leading Through Change: Why 21st Century Leadership Demands Reinvention, Resilience, and Radical Inclusion
By Aaron Schumm, CEO & Founder, Vestwell
In the 21st century, leaders are navigating one of the most dynamic and challenging business environments in history. From the rise of AI and the demands of a modern workforce to shifting global demographics and widening financial inequities, today’s executives are being asked to lead in fundamentally new ways.
At this year’s Milken Institute Global Conference, I had the opportunity to speak alongside visionary leaders from CalPERS, Oliver Wyman, Carta, and the University of Chicago Booth School of Business. Our panel, 21st Century Lessons in Leadership, explored how leadership is being redefined in an age of transformation, and what it takes to lead organizations, industries, and communities into the future.
AI: Empowering People, Not Replacing Them
AI was a consistent thread throughout the discussion. At Vestwell, we see AI as a tool to optimize the impact of each employee, unlocking more innovative, faster, and personalized experiences for the savers, advisors, and employers we serve. Whether it’s streamlining plan administration or delivering tailored saver engagement, we believe technology should elevate people, not sideline them. This belief was echoed by fellow panelists, who emphasized the importance of using AI to create value through innovation.
From Founder to Scaler
I also spoke to the personal evolution required as a founder transitions into a scaling CEO. Leading a startup takes vision; scaling it takes reinvention. At Vestwell, that has meant building not just a great product, but an ecosystem, one that now supports over 350,000 businesses and 1.5 million savers. True leadership today requires clarity of purpose, consistency of execution, and the agility to adapt without losing sight of your mission.
Building Culture in a Hybrid World
Culture remains one of the most complex challenges in the era of remote and hybrid work. While flexibility has become a baseline expectation, we've seen firsthand how it can also create silos and weaken connection, especially for early-career employees. That's why we're investing in regional hubs and intentional in-person experiences to reinforce collaboration and mentorship while maintaining the agility today’s teams require. As Marcie Frost of CalPERS emphasized, a strong culture is rooted in clarity, purpose, and trust.
Financial Security as a Leadership Responsibility
Leadership today extends far beyond the walls of any one company. The Milken Institute’s Lifetime Financial Security initiative underscores the pressing need to close the savings gap, with nearly half of Americans still lacking access to a workplace retirement plan.
Beyond our own companies, business leaders must also recognize their role in shaping a more inclusive financial future. Financial education and early saving are not yet the norm, and the gaps are even wider across underserved and underrepresented communities. On top of that, people are living longer than ever before, extending the need for retirement security by decades.
These realities underscore the urgency behind Vestwell’s mission. We're working to close access gaps through partnerships with payroll providers, fintech platforms, and state-sponsored programs. Our digital-first infrastructure helps deliver scalable, inclusive, and low-friction savings solutions that reflect the workforce we serve.
Moving From Volatility to Vision
The biggest takeaway from this year's Milken discussions? It's not just about navigating change, it's about owning it. Leaders must rethink traditional models, ground decisions in human needs, and prepare for a future where demographics, economics, and expectations are all in flux.
With the U.S. savings gap approaching $50 trillion and the population aging rapidly, the stakes are high. But so is the opportunity. Leadership in the 21st century isn’t about keeping up—it’s about moving forward with purpose.
