A reflective exploration of quiet resilience, professional transformation, and the enduring value of experience and integrity for women navigating career reinvention and meaningful leadership in an evolving world.
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Setbacks reveal whether your identity is rooted in what you do or who you are. People are remembered because their setbacks never had the final word.
Maedean Johnson · In Her Own Words
Her Story
About Maedean
Maedean is an insurance transformation leader whose career spans underwriting, product development, operational excellence, training, and technology enablement. With deep expertise in commercial insurance, she has built a reputation for connecting business strategy, underwriting expertise, and process improvement to drive meaningful organizational transformation. Beginning her career as a small business underwriter at The Hartford, Maedean went on to spend 14 years at CNA, where she developed extensive experience across small business and middle market underwriting, technology risks, cyber liability, errors and omissions, and core property and casualty lines. Throughout her career, she has been recognized not only for her technical underwriting expertise but also for her ability to identify opportunities where people, processes, and technology can work more effectively together.
At Zurich North America, Maedean played a pivotal role in one of the organization's largest underwriting modernization efforts, serving as an underwriting subject matter expert for a platform transformation initiative that consolidated approximately 13 legacy systems into a single underwriting platform. Acting as a bridge between underwriting, technology, and business operations, she helped design solutions that aligned with how underwriters evaluate risk and make decisions. She later joined Zurich's Underwriting University, where she developed onboarding journeys, training programs, and learning experiences that strengthened underwriting capabilities across the organization. Her contributions earned multiple industry and company recognitions, including two Zurich Impact Awards for underwriting innovation, platform development, and talent development initiatives.
Today, Maedean is the founder of Onward Insurance Strategy LLC, a consulting practice focused on underwriting transformation, insurance product enablement, platform strategy, operational improvement, training, and AI readiness. Her approach is grounded in the belief that successful transformation requires more than implementing new technology—it demands clarity, intentionality, and a deep understanding of the people who use the systems being built. A certified Scrum Product Owner, Lean Six Sigma Green Belt, and AI Operational Excellence Professional, she combines technical expertise with a passion for leadership and continuous improvement. Beyond her professional accomplishments, Maedean is a proud mother and grandmother whose values of faith, resilience, service, and legacy continue to shape her leadership philosophy and commitment to helping organizations and individuals move forward with purpose.
Her Interview
Ten minutes with Maedean
01What do you attribute your success to?
I attribute much of my success to how I was raised. My parents came from very humble beginnings and did not have many of the opportunities they worked so hard to give my sister and me. I watched them sacrifice, persevere, and create possibilities for us that were not always available to them.
When I was younger, I did not fully understand the weight of what they were doing. As I have grown, I have come to appreciate that their sacrifices shaped my values, my work ethic, my resilience, and the way I show up in the world. In many ways, how I live, how I work, and how I treat people is my way of honoring all they poured into me. I also believe my success has come from being willing to step into opportunities that were not always visible, glamorous, or immediately rewarded. Some of the assignments that changed the course of my career were the ones other people did not necessarily want to do. They stretched me, exposed me to new people and ideas, and prepared me for opportunities I could not have seen at the time. Looking back, I believe success is often built through faith, preparation, humility, hard work, and the willingness to keep growing before anyone is applauding. My parents gave me the foundation, and I have tried to honor that foundation by moving through my life and career with integrity, purpose, and gratitude.
02What’s the best career advice you’ve ever received?
The best career advice I have received is to never compromise my integrity for opportunity. Careers are built through skill, experience, and results, but they are sustained by character. That advice has guided me through many seasons of my professional life. I have learned to do the work well, tell the truth, treat people with respect, and leave things better than I found them. Opportunities may change, but integrity is something you carry with you into every room.
03What advice would you give to young women entering your industry?
My advice to younger women would be do not chase only the title or the money. Those things matter, but they will only take you so far if you have not built the character, discipline, relationships, and experience to sustain them. Look for opportunities to learn, even when they do not look glamorous. Be willing to grow where you are before rushing to the next role. Every assignment has something to teach you, and sometimes the work that feels small in the moment is preparing you for something much larger later. I would also tell younger women to build genuine relationships and be mindful of how they treat people at every level. Careers are long, industries are smaller than they seem, and the same people you meet early in your journey may cross your path again in unexpected ways.
Most importantly, treat people with respect, whether they are an underwriting assistant, a coworker, a janitor, a receptionist, or the president of the company. Your character is revealed by how you treat people who can do nothing for you. Titles may open doors, but integrity, humility, and respect are what allow you to keep walking through them.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges and opportunities in the insurance industry right now is preparing people for the pace of change. Technology, automation, data, and AI are reshaping how underwriting and insurance operations are being performed. The opportunity is tremendous, but only if organizations prepare their people, processes, and workflows for meaningful transformation.
Too often, companies believe transformation means implementing a new system. But true transformation requires more than technology. It requires understanding the work, improving the process, designing better workflows, and helping people shift from “this is how we have always done it” to “how can we do this better?” That mindset shift is one of the biggest challenges in the industry.
I believe transformation should not be positioned as replacing underwriters. It should be designed to support them. The goal should be to give underwriters better information, clearer workflows, stronger decision support, and more time to focus on judgment, strategy, and risk evaluation. When done well, transformation helps people make better decisions rather than removing the value they bring.
On a more personal level, one of the challenges I have faced as a woman, and especially as an African-American woman, is making sure my voice is heard and my expertise is recognized. There have been times when I could tell I was not what people expected when I walked into the room. But once the conversation began, my knowledge, preparation, and experience created a different level of respect. That has reinforced something important for me: value has a way of speaking. I may not always fit someone’s initial expectation, but I know what I bring to the table. My responsibility is to remain prepared, grounded, and confident enough to use my voice with clarity and purpose.
05What values are most important to you in your work and personal life?
Integrity is one of the most important values in both my work and my personal life. I often say I value people whose “who” matches their “do.” In other words, I respect people who are authentic, who stand by their word, who treat others with respect, and who can be trusted to do the right thing even when no one is watching. I also value humility, accountability, faith, service, and a willingness to do the work that may not always be visible or glamorous, but is necessary. Some of the most meaningful growth in my career came from rolling up my sleeves, stepping into difficult assignments, and doing what needed to be done because it mattered. In my work, I care deeply about leaving people, processes, and organizations better than I found them. In my personal life, those same values guide how I show up for my family, my relationships, and my community. For me, success is not just about achievement. It is about character, consistency, purpose, and being able to look back and know that I moved with integrity.
Her Content Hub
Articles by Maedean
Onward: Choosing Purpose, Integrity, and Reinvention
A quiet declaration of purpose: why experienced women belong in conversations shaping the future.
There are moments in life when moving forward is not loud. It is not dramatic. It does not always come with applause, certainty, or a perfectly drawn map.
Sometimes moving forward is quiet.
It is the decision to get up after disappointment. It is the choice to keep your character intact when circumstances test it. It is the courage to believe that your experience still has value, even when a season ends differently than you expected.
For me, the word onward has become more than a direction. It has become a declaration.
Experience at the Intersection of People, Process, and Systems
I have spent much of my professional life in the insurance industry, beginning in underwriting and later moving into transformation, technology-enabled workflows, process improvement, and business modernization. My work has often sat at the intersection of people, process, judgment, and systems. I have seen firsthand how complex work can become clearer when experience is respected, intent is captured, and technology is designed to support—not replace—human expertise.
But beyond the titles, projects, systems, and outcomes, my career has also taught me something more personal: growth often requires the willingness to evolve before the world fully understands what you are becoming.
Like many women, I have had seasons in which I had to advocate for myself, rebuild my confidence, and remind myself that a closed chapter is not the same thing as a failed story. There are times when your contribution may be visible, but your value may still be underestimated. There are times when doing the right thing may cost you comfort. There are times when integrity feels lonely before it feels rewarding.
Integrity Is Never Wasted
Yet I have learned that integrity is never wasted.
- It becomes part of your foundation.
- It shapes how you lead.
- It influences how you build.
- It reminds you that success is not only about what you achieve, but also how you carry yourself while achieving it.
Reinvention Belongs to Those Who Are Willing to Keep Becoming
As women, many of us have been conditioned to shrink our stories, soften our voices, or wait for permission to step into the next version of ourselves. We may question whether we are too experienced to start something new, too late to pivot, too careful to be bold, or too humble to be visible.
But reinvention is not reserved for the young. It is not reserved for the fearless. It is not reserved for people who have never been disappointed.
Reinvention belongs to those who are willing to keep becoming.
In my own journey, I have come to understand that experience is not something to hide or minimize. It is wisdom. It is pattern recognition. It is resilience. It is the ability to see what others may miss because you have lived through enough cycles to understand both opportunity and risk.
That matters. It matters in business. It matters in leadership. It matters in transformation. It matters in rooms where decisions are being made about the future.
Experienced Professionals Must Remain Part of the Conversation
Today, as industries explore artificial intelligence, automation, and new ways of working, I believe it is especially important for experienced professionals—particularly women—to remain part of the conversation. Technology may be advancing quickly, but wisdom still matters. Judgment still matters. Context still matters. Ethics still matter. The people who understand the work beneath the workflow have something essential to contribute.
I believe women bring a powerful lens to transformation because we often understand what it means to navigate complexity, adapt under pressure, and lead through ambiguity. We know how to connect details to outcomes. We know how to listen for what is not being said. We know how to build bridges between strategy and reality.
That is not a soft skill. That is leadership.
Empowerment and Making Room for Other Women
Empowerment, to me, is not about pretending every experience has been easy. It is about refusing to let difficulty have the final word. It is about taking what you have learned and allowing it to serve a greater purpose. It is about moving forward with both confidence and humility.
It is also about making room for other women to do the same.
One of the most powerful things we can do for each other is remind one another that we are not finished. Not after a setback. Not after a transition. Not after a career shift. Not after being underestimated. Not after choosing integrity over convenience.
- We are still capable of building.
- We are still capable of learning.
- We are still capable of leading.
- We are still capable of becoming more fully ourselves.
Moving Onward
For me, moving onward means carrying the lessons without carrying bitterness. It means honoring the work I have done while remaining open to the work still ahead. It means using my voice to bring clarity where there is confusion, structure where there is friction, and humanity to a conversation that technology is rapidly changing.
It means believing that purpose does not expire.
To every woman standing at the edge of a new chapter, I would say this: Do not confuse uncertainty with inadequacy. Sometimes uncertainty is simply the space between who you were and who you are becoming.
- You do not have to have every answer to take the next step.
- You do not have to diminish your past to embrace your future.
- You do not have to become someone else to be powerful.
Your experience counts. Your voice counts. Your integrity counts. And the wisdom you have earned along the way may be exactly what someone else needs to see what is possible.
So, take the step.
- Not because the road is easy.
- Not because the timing is perfect.
- Not because everyone understands.
Take the step because there is still purpose ahead.
Onward.
A reflective exploration of quiet progress, professional wisdom, and the power of women embracing reinvention with integrity. This piece celebrates how experience, resilience, and authentic leadership shape meaningful transformation.
Onward: Choosing Purpose, Integrity, and Reinvention
Finding Purpose in the Quiet Moments of Growth and Reinvention
There are moments in life when moving forward is not loud. It is not dramatic. It does not always come with applause, certainty, or a perfectly drawn map.
Sometimes moving forward is quiet.
It is the decision to get up after disappointment. It is the choice to keep your character intact when circumstances test it. It is the courage to believe that your experience still has value, even when a season ends differently than you expected.
For me, the word onward has become more than a direction. It has become a declaration.
Experience at the Intersection
I have spent much of my professional life in the insurance industry, beginning in underwriting and later moving into transformation, technology-enabled workflows, process improvement, and business modernization. My work has often sat at the intersection of people, process, judgment, and systems. I have seen firsthand how complex work can become clearer when experience is respected, when intent is captured, and when technology is designed to support-not replace-human expertise.
But beyond the titles, projects, systems, and outcomes, my career has also taught me something more personal: growth often requires the willingness to evolve before the world fully understands what you are becoming.
Like many women, I have had seasons where I had to advocate for myself, rebuild my confidence, and remind myself that a closed chapter is not the same thing as a failed story. There are times when your contribution may be visible, but your value may still be underestimated. There are times when doing the right thing may cost you comfort. There are times when integrity feels lonely before it feels rewarding.
Integrity Is Never Wasted
Yet I have learned that integrity is never wasted.
It becomes part of your foundation. It shapes how you lead. It influences how you build. It reminds you that success is not only about what you achieve, but how you carry yourself while achieving it.
As women, many of us have been conditioned to shrink our stories, soften our voices, or wait for permission to step into the next version of ourselves. We may question whether we are too experienced to start something new, too late to pivot, too careful to be bold, or too humble to be visible.
But reinvention is not reserved for the young. It is not reserved for the fearless. It is not reserved for people who have never been disappointed.
Reinvention belongs to those who are willing to keep becoming.
Experience Is Wisdom
In my own journey, I have come to understand that experience is not something to hide or minimize. It is wisdom. It is pattern recognition. It is resilience. It is the ability to see what others may miss because you have lived through enough cycles to understand both the opportunity and the risk.
- That matters in business.
- It matters in leadership.
- It matters in transformation.
- It matters in rooms where decisions are being made about the future.
Today, as industries explore artificial intelligence, automation, and new ways of working, I believe it is especially important for experienced professionals, particularly women, to remain part of the conversation. Technology may be advancing quickly, but wisdom still matters. Judgment still matters. Context still matters. Ethics still matter. The people who understand the work beneath the workflow have something essential to contribute.
I believe women bring a powerful lens to transformation because we often understand what it means to navigate complexity, adapt under pressure, and lead through ambiguity. We know how to connect details to outcomes. We know how to listen for what is not being said. We know how to build bridges between strategy and reality.
That is not soft skill. That is leadership.
Empowerment and Making Room
Empowerment, to me, is not about pretending every experience has been easy. It is about refusing to let difficulty have the final word. It is about taking what you have learned and allowing it to serve a greater purpose. It is about moving forward with both confidence and humility.
It is also about making room for other women to do the same.
One of the most powerful things we can do for each other is remind one another that we are not finished. Not after a setback. Not after a transition. Not after a career shift. Not after being underestimated. Not after choosing integrity over convenience.
- We are still capable of building.
- We are still capable of learning.
- We are still capable of leading.
- We are still capable of becoming more fully ourselves.
Moving Onward
For me, moving onward means carrying the lessons without carrying bitterness. It means honoring the work I have done while remaining open to the work still ahead. It means using my voice to bring clarity where there is confusion, structure where there is friction, and humanity where technology is rapidly changing the conversation.
It means believing that purpose does not expire.
To every woman standing at the edge of a new chapter, I would say this: do not confuse uncertainty with inadequacy. Sometimes uncertainty is simply the space between who you were and who you are becoming.
- You do not have to have every answer to take the next step.
- You do not have to diminish your past to embrace your future.
- You do not have to become someone else to be powerful.
Your experience counts. Your voice counts. Your integrity counts. And the wisdom you have earned along the way may be exactly what someone else needs to see what is possible.
So, take the step.
- Not because the road is easy.
- Not because the timing is perfect.
- Not because everyone understands.
Take the step because there is still purpose ahead.
Onward.
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