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Curiosity, Hustle, and Connecting the Dots: Ron’s Journey from Entry-Level to Transformative Tech Leader

In a world where technology and leadership are in constant flux, Ron’s career story is a beacon of inspiration. From his humble beginnings as an entry-level employee at Toyota to becoming a transformative leader and CIO across multiple industries, Ron’s path is defined by an unyielding curiosity, a relentless drive rooted in his immigrant heritage, and a unique talent for bridging technology with human impact. His journey is one of perseverance, continuous improvement, and a vision for the future beyond corporate success. In this candid conversation, Ron shares the key lessons that shaped his approach to leadership, offers actionable insights, and discusses the mindset that has propelled him to the forefront of innovation.

Curiosity as the Core of Leadership

Curiosity is a fundamental pillar of Ron’s leadership style. It’s not just about asking questions—it’s about seeking a more profound understanding and context. From a young age, Ron’s passion for history sparked an intense desire to explore why things happen the way they do. “I’ve always wanted to know why things are the way they are,” Ron explains. His love for history, whether ancient military strategies or economic trends, has equipped him with a broad perspective that he brings into every decision.

This insatiable curiosity has guided his career, pushing him to challenge the status quo and delve into the underlying causes of problems rather than simply addressing the symptoms. “Context is everything,” Ron emphasizes. By understanding the broader historical, cultural, and organizational context, he has been able to lead with clarity and empathy, navigating complex situations with a nuanced approach.

Ron’s commitment to fostering a culture of inquiry has empowered his teams to think critically and innovate. He encourages his team members always to ask “why” and to challenge assumptions. This culture of curiosity not only drives deeper insights but also fuels continuous learning, making his teams more adaptable and resilient in the face of change.

The Immigrant Hustle: Fueling Relentless Motivation

Ron’s drive can be traced back to his roots as the son of Haitian immigrants who fled political turmoil in search of a better life in the United States. This experience instilled in him a powerful sense of responsibility and a relentless work ethic. “There’s this immigrant hustle,” Ron says, “a feeling that you have to thrive because someone before you sacrificed everything.”

This mentality has shaped his approach to leadership, pushing him to excel and expect the same level of commitment from his teams. For Ron, success isn’t just a personal achievement—it’s a way of honoring the sacrifices made by his parents. His visits to Haiti before and after the earthquake have only deepened his appreciation for their journey. “I want my legacy to be one of striving for more, to ensure that the sacrifices made by my parents were not in vain,” he reflects.

This immigrant mindset isn’t just about hard work—it’s about making the most of every opportunity and tackling challenges head-on. He’s instilled this value in his own children, who have pursued ambitious careers in law and AI mathematics, embodying the same spirit of perseverance. By sharing his story with his teams, Ron inspires them to embrace this same grit and determination, encouraging them to push beyond their perceived limits and make the most of the opportunities before them.

Continuous Improvement: Embracing the Kaizen Philosophy

Ron’s tenure at Toyota was a transformative chapter that shaped his leadership philosophy. He embraced Toyota’s core principle of “kaizen”, or continuous improvement, from starting his career in an entry-level collections role. “I began my career knocking on doors for collections, and I left as CIO of the Financial Services Division,” Ron recalls. “It was a 19-year journey of embracing the idea that we must always strive to improve.”

“Kaizen” became Ron’s guiding philosophy, influenced by the teachings of W. Edwards Deming, whose focus on quality control and process optimization left a lasting impact on Toyota’s business practices. “It’s about thinking globally but operating locally,” Ron explains. He applied this mindset throughout his career as a framework for refining processes and driving incremental improvements.

At Farmers Insurance, he implemented “kaizen” principles during the California wildfires, ensuring that the company’s systems were resilient enough to handle emergency claims efficiently. “We are here to provide service when it matters most,” he says. “It’s not just about technology—it’s about being there for people when they need us.”

Ron’s commitment to continuous improvement is evident in every role he’s taken on. He believes that success lies in the details and that small, incremental changes can lead to significant transformations over time. By embedding a culture of feedback and adaptation, Ron has built high-performing teams capable of meeting the tech industry’s dynamic challenges.

Connecting Technology to Human Impact

One of Ron’s most notable leadership strengths is his ability to bridge the gap between complex technology and its real-world applications. He has a unique talent for connecting the dots and making technology meaningful and relevant to the people it serves. “In tech, we’re often like the Wizard of Oz,” Ron quips. “We’re so removed from the actual outcome that we forget why we’re doing this.”

To counter this disconnect, Ron has prioritized tying every technological decision back to its human impact. At Toyota, he reframed the work of his finance team, emphasizing that they weren’t just managing transactions—they were enabling families to buy cars that would safely transport their children. “We deliver dreams,” Ron would tell his team, highlighting the deeper purpose behind their tasks.

This focus on human impact continued at Farmers Insurance, where he ensured the tech team understood the importance of system readiness, particularly during crises. “No one calls an insurance company at 2 a.m. for fun,” Ron notes. “We need to be ready when it matters most, connecting our technical work to the real people it affects.”

Ron’s ability to link technology projects with tangible outcomes has created a shared sense of purpose among his teams. This approach has driven engagement and enhanced the effectiveness of his projects, delivering real value to the end-users and the organization.

Leading Change and Championing Digital Equity

For Ron, being a CIO is about more than managing technology—it’s about leading change and positively impacting society. He sees himself as a change agent guiding his organization through complex transitions. “Technology isn’t just about the latest gadget,” he asserts. “It’s about convincing people to adopt change and embrace new ways of doing things.”

Ron’s current focus is on digital equity, a pressing issue as AI and digital transformation evolve rapidly. His doctoral research explores how AI can bridge or exacerbate the gap between different social groups. “We often talk about the digital divide,” he says, “but I prefer the term digital redlining—it’s an intentional marginalization that must be addressed.”

He is particularly concerned about the unconscious biases embedded in AI systems, which can perpetuate inequality. “How do we ensure our AI platforms don’t absorb our biases?” he asks. This question drives his ongoing work to build a more equitable digital landscape.

At Save the Children, Ron champions initiatives to bring STEM education to underserved communities, both in the U.S. and globally. “Digital natives today consume technology, but we haven’t taught them to harness its power effectively,” he observes. We need to prepare the next generation for where the puck is going, not where it is now.”

Building on Ron’s Leadership Blueprint

Inspired by Ron’s journey? Here’s how you can implement his principles in your leadership:

  1. Cultivate Curiosity: Embrace a mindset of inquiry and encourage your team to ask more profound questions. Understanding the context behind decisions leads to better insights and more innovative solutions.
  2. Leverage Diverse Experiences: Draw on your team members’ diverse backgrounds. Like Ron, harness the unique perspectives from different life experiences to drive creativity and resilience.
  3. Implement Continuous Improvement: Adopt the philosophy of “kaizen.” Focus on small, incremental changes and embed a culture of feedback to drive ongoing enhancements.
  4. Connect Technology to Real-World Impact: Ensure that your team understands the human side of technology projects. Use storytelling to frame their work for its broader purpose, aligning efforts with tangible outcomes.
  5. Champion Digital Equity: Lead with a focus on inclusivity and fairness. Address unconscious biases in your tech projects and advocate for digital inclusion initiatives that extend opportunities to underserved communities.
  6. Be a Change Agent: Embrace your role as a catalyst for transformation. Set a bold vision, lead empathetically, and inspire your team to adapt and innovate.

Ron’s story is one of transformation and tenacity, shaped by a deep-rooted curiosity, an immigrant’s relentless drive, and a commitment to making technology meaningful in the lives of everyday people. From knocking on doors in collections at Toyota to leading global technology teams and driving digital transformation across multiple industries, Ron has consistently shown what it means to be a true leader. He has always retained sight of the human impact of his work, always striving to connect technology with tangible benefits and focusing on continuous improvement along the way.

Now, as he steps into the future with a focus on digital equity and empowering the next generation through STEM education, Ron’s vision extends far beyond the corporate landscape. He is driven by a mission to use technology as a catalyst for social good, ensuring that the tools of the digital age are accessible and equitable for all. His leadership journey is an inspiring example of how curiosity, resilience, and a deep sense of responsibility can propel a career and make a lasting impact on society.

Ron is more than just a technology executive—he’s a mentor, a change agent, and a visionary leader who continues to push the boundaries of what’s possible in the world of tech and innovation. His legacy will be marked not only by the systems he’s built or the teams he’s led but also by the countless lives he’s touched along the way.