The Human Side of Technology: Resilience, Reinvention, and My Journey Toward Leadership

Jeffrey Cortez
Oct 16
16 min read

Every career is a journey, but not every journey is a straight line. Mine has been a roller-coaster—marked by soaring wins, humbling setbacks, and hard-won lessons about what it really means to lead. Through it all, I’ve discovered a truth that shapes the way I see my work today: technology is not about machines, systems, or code. It’s about people. It’s about trust, creativity, resilience, and the pursuit of meaning.

In 2025, I reached a personal milestone I had dreamed about for decades—earning my Executive Master’s in Technology Management from Columbia University. That achievement gave me the chance to look back at the path that brought me here, to see how every chapter of my journey was preparing me to step into the leadership role.. What I found wasn’t just a resume—it was a story. One of financial discipline, functional excellence, emotional intelligence, identity forged through resilience, and meaning discovered in unexpected places.

Bank Street College of Education: Where Trust Became the Foundation of My Leadership

I still picture the Grand Morningside Heights campus of Bank Street—its stately brownstone façade on West 112th Street, nestled among academic giants, brimming with creative chaos and a commitment to progressive education. Here, at a hub devoted to nurturing children and educators, I first discovered that technology wasn’t merely about systems—it was about sustaining trust.

One late afternoon, a teacher named Maria rushed into my office holding her iPad in one hand and a toddler’s drawing in the other. “Jeff,” she said, her voice trembling, “if these classrooms go dark, we lose more than lesson plans—we break trust with kids who depend on us.” Her urgency wasn't alarmist—it was heartfelt. It underscored what Bank Street is all about: radical care for learners, grounded in community.

Bank Street didn’t just teach children. It pioneered tools like the Bank Street Writer, one of the earliest educational word processing applications, shaping how students learned to express themselves through technology. Decades later, I found myself becoming not only a steward of servers but also a guardian of that spirit—the bridge between progressive educational ideals and real-world functionality.

In meetings with the Strategy & Operations team, I learned that our Help Desk wasn’t simply trouble-shooting equipment. It was protecting the creative flow of classroom projects, workshops, and student explorations. When a server struggled, teachers weren’t just inconvenienced—they lost lessons, moments, and morale. Maintaining uptime wasn’t just operationally critical, it was emotionally significant.

One evening at an event hosted by the Bank Street Education Center—where educators, policymakers, and families converged to envision equitable learning—I found myself speaking with a veteran director. She shared how the systems we supported allowed her to pilot “Emotionally Responsive Practice” workshops, embedding social-emotional learning into curriculum design. In that exchange, I saw that my work—though technical—underpinned profound human impact.

At Bank Street, the technology I managed wasn’t just functional—it was foundational to meaning and identity. It enabled joyful, learner-centered environments that honored every child and educator. That institution taught me: leadership in technology starts with empathy, community, and the unwavering belief that our work serves something larger than any network.

Rainforest Alliance: When Technology Became a Global Lifeline

The first thing that struck me at the Rainforest Alliance was how mission and technology intertwined in ways I had never seen before. The organization wasn’t just headquartered in New York—it was in the field, deep in coffee-growing cooperatives in Latin America, forests in Africa, and farms in Southeast Asia. Our work in IT wasn’t abstract. Every system, every server, every login connected directly to people trying to protect ecosystems, earn a living wage, and bring sustainability to scale.

One afternoon I was on a video call with a field coordinator in Guatemala. The connection was fragile—each word broken by static—but the urgency was clear. “Jeff, we need the reporting system to hold. Farmers are waiting. Without certification, they lose contracts.” I could see the worry on his face. For him, uptime wasn’t just a matter of convenience—it was the difference between a family being able to sell their crop that season or losing everything.

At Rainforest, I migrated our core infrastructure into the cloud, cutting costs by almost half while dramatically improving reliability. But the real impact was not in the balance sheet—it was in what that reliability meant to people like the farmers depending on certification systems, or the sustainability managers trying to track deforestation metrics across continents. When a report generated cleanly, it didn’t just tick a compliance box—it safeguarded livelihoods, ensured accountability, and built trust with global partners.

I remember walking through the New York office where maps of the Amazon, Central America, and East Africa lined the walls. Each dot represented communities relying on our systems to record their progress and validate their hard work. Sitting at my desk, I felt the weight of those dots. Technology here wasn’t theoretical—it was the nervous system of a movement.

That year taught me that technology at global scale is not simply about efficiency—it is about perspective. I learned to design not for one institution, but for thousands of voices across dozens of countries, each depending on technology to be seen, heard, and validated. It deepened my understanding that functional systems must always serve financial and emotional realities too. They allow people to prove their value, sustain their families, and claim their identity as stewards of the earth.

At Rainforest Alliance, I began to see technology not only as infrastructure, but as a lifeline. And I began to see myself not only as an IT leader, but as a global partner—responsible for ensuring that a farmer’s harvest in Guatemala, a community’s conservation plan in Ghana, or a sustainability report in New York could all find common ground through systems designed to serve people first.

Tekserve: The Rise, the Collapse, and the Lesson of Resilience

Walking into Tekserve in those days was like stepping into a temple for technologists. The loft-style space in Chelsea was iconic—an eclectic mix of vintage Macs lining the walls, quirky mechanical displays, the faint glow of neon, and the famous 10-cent Coke machine buzzing in the corner. Long before Apple opened its glass palaces, Tekserve was New York’s Apple store—a place where artists, filmmakers, designers, and corporations alike came for advice, gear, and the kind of technical wizardry that blended engineering with artistry.

As Director of Technology/CTO, I was in the middle of this whirlwind. We were pushing boundaries—architecting cloud-agnostic, zero-trust infrastructures, building containerized pipelines, and designing Production-as-a-Service platforms so creative teams could edit films and share content seamlessly from anywhere in the world. The energy was electric. I remember one late night huddled with engineers, marker stains on our sleeves, sketching out a CI/CD flow that we knew would shave days off client production cycles. At Tekserve, every project felt like an act of invention.

But while the floor buzzed with innovation, the walls were tightening. Competition from Apple’s direct-to-consumer stores was eroding retail margins. Rent in Chelsea soared. Even as our technical offerings expanded, the financial ground beneath us weakened. And then one day, the news we had feared arrived: Tekserve was closing.

The memory of that moment is seared into me. The hum of the server room, once alive with possibility, suddenly sounded like a countdown. Around me, colleagues stared blankly at their screens, whispered in hallways, or sat silently at their desks. One designer packed up her workstation with tears in her eyes. An engineer, exhausted, looked at me and asked softly: “Jeff, what do we do now?”

In that moment, my role shifted. No architecture, no pipeline, no redundancy plan could stop what was happening. What I could do was show up as a leader. I sat with colleagues, helped them refine resumes, made introductions, and—most importantly—listened. I told them what I believed to be true: that the systems we had built mattered, that their ingenuity mattered, and that what we learned together would carry us forward even if the company did not.

Losing Tekserve was heartbreaking. For me, it was more than the collapse of a company—it was the collapse of a community I loved. Yet in that crucible, I discovered resilience. I learned that technology cannot save a business model misaligned with market realities. I learned that leadership isn’t about titles or flawless track records, but about standing with people in their hardest hours. And I learned to redefine my identity—not as a product of a single company, but as a leader who brings purpose and steadiness wherever I go.

Looking back, Tekserve gave me one of the most important lessons of my life: that meaning in technology leadership comes not only from the systems we design, but from the people we serve when those systems—and sometimes even the organizations around them—fail.

Amur Capital: Navigating a CEO-Centric World and Earning Trust in the Short Term

If Tekserve had taught me resilience, Amur Capital tested my ability to adapt quickly and build trust in an environment unlike any I had encountered before. Amur wasn’t a traditional finance firm with siloed departments and predictable hierarchies—it was a management company overseeing a constellation of affiliated businesses. Every decision, every initiative, every project seemed to revolve around the CEO, whose vision and drive shaped the organization’s culture.

From my first day, I understood that success here wasn’t just about rolling out technology strategies—it was about building credibility fast. I walked into meetings where the CEO’s perspective carried absolute weight. People around the table often waited for his nod before moving forward. In that kind of environment, the challenge wasn’t technical—it was relational. How do you establish yourself as a leader when the gravitational pull of the organization orbits so strongly around one person?

My strategy was simple: listen first, act fast, and deliver value visibly. I didn’t have years to cultivate trust—I had weeks. I spent time with global teams across engineering, compliance, and finance, asking not just about systems but about pain points. “What keeps you up at night?” I’d ask. One risk officer told me bluntly, “Jeff, we don’t need promises, we need clarity. If a system goes down during a deal, it’s not just inconvenient—it’s catastrophic.” That candor gave me my mandate: shore up reliability while modernizing for the future.

I began architecting a roadmap that could both align with the CEO’s high-velocity vision and reassure teams that stability wouldn’t be sacrificed for speed. We integrated AI-powered analytics to improve forecasting, but we also strengthened governance frameworks to give leadership confidence in every number they saw. It wasn’t about dazzling with innovation for its own sake—it was about showing that technology could be both forward-looking and trustworthy.

But the heart of the experience wasn’t in the systems we deployed—it was in the relationships. I still remember a tense moment during an M&A integration call. Teams from two countries, uncertain about their future, were reluctant to share data. The CEO pushed hard for results, but I realized the problem wasn’t technical—it was human. So I paused the meeting, shifted the conversation away from compliance checklists, and simply acknowledged their anxiety. That moment broke the tension. We found a way forward—not because I wrote better scripts, but because I created space for people to be heard.

In the end, my time at Amur was short. But it left a lasting impression on me. I learned that leadership in a CEO-driven culture isn’t about competing with the gravity of the founder’s influence—it’s about complementing it, amplifying it, and building the trust of those who orbit within it.

What I carried with me was this: even in the most centralized environments, leadership is still about people. It’s about listening deeply, moving quickly, and proving through actions—not words—that technology can be a stabilizing force in the midst of rapid change.

Wildlife Conservation Society: Doing More With Less for Mission and Meaning

Walking into the Bronx Zoo—the flagship of the Wildlife Conservation Society—was unlike any office I’d ever entered. Instead of marble lobbies or trading floors, my commute often ended with the sound of children laughing near the sea lion pool or the sight of keepers tending to animals. The backdrop of conservation work was everywhere. And yet behind the scenes, the technology challenges were just as complex as any global finance firm I’d known.

WCS wasn’t about chasing quarterly numbers—it was about preserving species, educating millions of visitors, and sustaining a 125-year mission across five zoos and aquariums in New York City. But like many nonprofits, resources were limited, budgets tight, and yet expectations sky-high. “Jeff,” a senior operations manager told me during my first week, “we need enterprise-grade systems—but we need them lean. Every dollar saved goes back to the animals and to conservation.” That conversation reframed my mission immediately: success here would be measured not just in uptime or KPIs, but in the impact on a mission far bigger than myself.

The challenge was daunting: modernize infrastructure, overhaul data warehousing, and integrate merchandising, ticketing, and food systems across all five parks. I remember one particular night at the zoo’s central operations office, the lights dim, when my small team and I finally deployed the new cloud-based ticketing system. Hours later, watching families stream through the gates the next morning with a smoother, faster entry experience was one of the most gratifying moments of my career. That wasn’t just efficiency—it was accessibility. It was families spending less time in line and more time creating memories together.

But the lean reality was always present. I’d walk past enclosures where biologists were improvising tools from scraps, or staff brainstorming ways to stretch small grants into full programs. Their ingenuity was contagious. It reminded me daily that scarcity can drive creativity. My job wasn’t to give them unlimited resources—that would never be possible—but to architect systems that stretched every dollar and made their work more impactful.

There was also a deep emotional layer. I remember speaking with a young educator who told me that the new mobile learning app we piloted allowed her to bring conservation lessons to children who might otherwise never visit a zoo. “You’re not just fixing servers,” she told me with a smile, “you’re helping us reach kids who will become tomorrow’s conservationists.” That moment crystallized for me that in a nonprofit, technology is never abstract—it is deeply personal.

At WCS, I learned the discipline of lean operations. But more importantly, I learned that technology leadership in a mission-driven world is about more than efficiency. It’s about meaning. Every improvement in system reliability was also an investment in trust with visitors. Every streamlined workflow gave staff more time to focus on animals and education. Every dollar saved kept conservation alive.

When I look back, I see WCS as the chapter that taught me that true innovation isn’t born only in abundance. Sometimes it flourishes most where constraints demand creativity, empathy, and a relentless focus on purpose.

Columbia University: Where Technology Met Humanity

Stepping into Columbia felt like stepping into two worlds at once. On one side, I was the Senior Database Specialist—the person responsible for keeping mission-critical systems secure, compliant, and scalable across a leading Ivy League institution. On the other, I was a teacher and mentor, introducing students as young as eight to the frontiers of artificial intelligence. It was a role that demanded both technical precision and human connection.

The technical side was formidable. I led the design and deployment of over thirty custom enterprise applications, modernizing data systems that touched everything from admissions to finance. I architected new workflows that integrated with FileMaker, aligning academic platforms and operational systems in ways that eliminated bottlenecks and gave administrators a real-time view of their data. I built roadmaps for transformation—plans that carried Columbia from legacy systems into a data-driven, cloud-integrated future.

But the moments that stayed with me most weren’t about code—they were about people.

One spring afternoon, I stood in front of a classroom of fifth graders for the first session of the Junior AI Innovators Program, a curriculum I had designed from scratch. I started by asking them: “What if computers could learn like we do?” A boy in the back raised his hand and said, “Does that mean my iPad could do my homework?” The room erupted in laughter, but in that moment, I realized something profound: introducing children to AI wasn’t just about teaching algorithms. It was about teaching them to imagine.

Over time, we built projects that blended generative AI with design thinking, guided by neuroscience-based approaches to learning. Watching students light up as they created their first AI-powered stories or designed simple robotics systems was exhilarating. They weren’t just consuming technology—they were shaping it. And I saw myself not just as their teacher, but as their partner in curiosity.

I also learned from colleagues. Columbia is a hub of global expertise, and in coffee-fueled conversations with professors and researchers, I absorbed perspectives on everything from ethics in AI to quantum computing. These weren’t just technical discussions—they were debates about equity, responsibility, and what kind of future we want to build.

And then, in 2025, I achieved something deeply personal: completing my Executive Master’s in Technology Management. It was the culmination of a dream that had been with me since the beginning of my career. I can still remember sitting in my final seminar, reflecting on the journey. The degree was more than a credential—it was a mirror. It showed me that my identity as a leader wasn’t only about systems and strategy, but about empathy, connection, and purpose.

At Columbia, I learned that technology leadership must always be human-centered. The systems I built supported compliance and efficiency, but the real transformation happened when technology became a tool for empowerment—whether for administrators making decisions, professors advancing research, or children learning to dream.

This chapter reminded me that leadership isn’t about being the smartest person in the room. It’s about asking the questions that unlock possibility, building bridges between disciplines, and creating environments where others can thrive. Columbia gave me humanity, and in doing so, it prepared me for the kind of leader I aspire to be: one who leads not just with knowledge, but with heart.

2Nspira: Building With Purpose

Finally, there is 2Nspira, the firm I founded to bring all of these lessons together. After decades of working within institutions of every size and culture, I wanted to create something different—a company that proved technology could be more than a service, more than a product, more than a bottom line. It could be a catalyst for equity, empowerment, and transformation.

Over six years, we grew by 300%. We modernized systems for schools and nonprofits that had been left behind by digital transformation. We integrated AI tools that gave leaders new clarity in decision-making. We built secure, cloud-based platforms that streamlined operations for organizations that once struggled under the weight of outdated systems. But 2Nspira was never just about numbers or contracts—it was about purpose.

One of my proudest achievements has been mentoring more than twenty underrepresented entrepreneurs. Some came to me with just an idea scribbled on a notepad, unsure whether they belonged in the world of startups. I remember one founder—a brilliant young woman—who hesitated to launch her product. “What if I fail?” she whispered, eyes full of doubt. I told her failure wasn’t the enemy—fear was. Months later she called me, voice trembling with joy, to say her company had signed its first contract. That moment wasn’t just about revenue. It was about identity, courage, and the meaning that comes from proving to yourself that you belong.

I saw this pattern again and again: entrepreneurs finding their voice, nonprofits reclaiming their time, educators using technology to amplify their mission instead of fighting against it. Each success wasn’t just a technical win—it was a human one.

Through 2Nspira, I proved to myself and to others that technology, when aligned with values—equity, trust, creativity, empowerment, and purpose-driven innovation—can transform not only organizations but lives. It reminded me that the real measure of leadership isn’t how many systems you deploy or budgets you control. It’s how many people you lift, how many voices you amplify, and how many futures you help unlock.

2Nspira is more than a consulting firm to me. It is the embodiment of everything my journey has taught me: that technology is most powerful when it is human-centered, equity-driven, and relentlessly purposeful. It’s not just the culmination of my career so far—it’s a vision of the kind of leadership I want to bring into every organization I serve.

Closing: Leadership With Heart and Purpose

As I look back across each chapter of my journey, I see more than titles or achievements—I see the values that shaped me into the leader I am today. At Bank Street, I learned that trust is the foundation of all technology. At the Rainforest Alliance, I discovered that functionality at scale can become a lifeline for families and communities. At Tekserve, I experienced the emotional truth of resilience—how leadership is defined not in moments of triumph but in moments of loss. At Amur Capital, I learned how identity and credibility must be forged quickly in high-pressure, CEO-driven environments. At the Wildlife Conservation Society, I saw how meaning can be found in doing more with less, ensuring every dollar saved and every system modernized supported a mission larger than ourselves. At Columbia University, I found humanity in leadership—blending strategy with empathy, and knowledge with curiosity.

And through 2Nspira, I’ve been able to weave all of those lessons together. Financial discipline gave us growth. Functional excellence gave us trust. Emotional intelligence gave us the ability to mentor and uplift. Identity shaped by resilience gave us courage to build differently. And meaning, always, gave us purpose—to ensure technology doesn’t just serve organizations, but transforms lives.

These five values—financial, functional, emotional, identity, and meaning—are no longer abstract ideas to me. They are the through-line of my career, the compass that has guided me from classrooms to rainforests, from boardrooms to zoos, from startups to Ivy League halls.

As I step into the next chapter of my leadership journey, I carry this compass with me. Because in the end, technology isn’t just about what we build—it’s about who we build it for, and why.

Gratitude

No journey is ever walked alone. This article is dedicated to the extraordinary people who have shaped my path and shared in my journey.

I am deeply grateful to the inspirational bosses and mentors who challenged me, stretched my thinking, and showed me what leadership with vision and courage can look like. Some of my most important lessons came not in boardrooms, but in quiet one-on-one conversations—sometimes over coffee, sometimes over laughter after a long day—where a single question or piece of advice stayed with me for years. Each of you planted seeds that continue to guide my decisions and shape the way I lead.

To my colleagues and teammates, thank you for standing shoulder to shoulder with me through the highs and the lows. I’ll always remember the late nights when we were huddled around whiteboards, brainstorming solutions until the markers ran dry, laughing at ourselves even as the deadlines loomed. Those moments taught me that leadership is not about standing above others, but alongside them, sharing both the weight and the joy of the work.

To my professors at Columbia University, thank you for broadening my perspective and pushing me to think more deeply about the role of technology in society. Our debates about strategy, governance, AI ethics, and human-centered innovation weren’t just academic—they were alive, filled with energy, disagreement, and discovery. You reminded me that the highest form of leadership is not technical mastery alone, but the courage to ask better questions and the humility to keep learning.

And to the many students, entrepreneurs, and professionals I have supported over the years—thank you for trusting me to be part of your journeys. I’ve been inspired by the brainstorming sessions where ideas leapt off the page, the moments of doubt that gave way to breakthroughs, and the celebrations when you achieved something you once thought impossible. Your courage to take risks has pushed me to dig deeper into my own skills and sharpen my purpose.

Every lesson, every partnership, every challenge has been a gift. For that, I carry immense gratitude—and an unshakable belief that the best kind of leadership is the kind that lifts others up, sparks laughter along the way, and reminds us that we’re always better when we build together.