I am Leonidas Caldwell, a mathematician, software engineering leader, and creative professional based in Flint and Detroit, Michigan. My career spans over a decade of experience in software development, enterprise architecture, automation, and financial technology. I've led high-stakes engineering projects at industry-leading companies, including Rocket Mortgage and Microsoft, delivering scalable solutions that drive operational efficiency and business growth.
Exploring the foundational elements that drive my approach to leadership and innovation
“Strong leadership is about building trust and inspiring excellence.”
Strong teams are the foundation of sustainable business success and building strong teams is at the core of my leadership philosophy. I have built and led high-performing teams that operate at a high level. Whether in education, corporate settings, or community organizations, I've prioritized creating a culture of accountability, trust, and shared goals.
“Mathematics is the foundation of logical thinking and problem-solving.”
Contrary to popular belief, Math isn't a science of numbers, it's the art and science of solving real world problems.
One of my favorite topics in mathematics was Optimization, the art of finding the maximum and minimum values in complex systems. In application, these problems translate into maximizing efficiency and minimizing waste.
This lens shaped much of my career, whether designing business processes, streamlining technology systems, or improving team workflows, the principles of optimization became a mindset I carry into every project.
“Education is the most powerful tool for creating opportunity.”
Education has always been central to my professional career. My career began in education as the Dean of Student Culture at International Preparatory Academy, where I developed programs and systems to enhance student engagement and academic performance.
I've extended my commitment to education by teaching and mentoring early and mid-career professionals, creating educational programs that bridge the gap between theory and real-world application. My work in education reflects my belief that empowering people with knowledge is the foundation for long-term success.
I am a creative with both a deep and wide understanding of technology-spanning from Fortune 500 enterprises to early-stage startups. My expertise covers the full technology stack, from system architecture and cloud infrastructure to data science and machine learning. I approach every challenge with a blend of technical expertise and creative problem-solving, ensuring that solutions are not only technically sound but also aligned with business goals.
Industries talks about innovation, new ideas, fresh perspective - all characteristics rooted by the creative process - I do it. As a creative problem-solver, I pull from concepts derived from both the creative and scientific processes and apply them in my pursuits. Doing so, I have shown significant impact at program, process, product and strategic levels at industry-leading institutions and within my communities.
“Merging creativity with technical precision to deliver meaningful solutions.”
Flintstone LLC is my consulting studio and creative lab - a place where I build, teach, and consult. I've delivered custom software, led infrastructure migration strategies, automated business processes, and even provided photography for personal and corporate storytelling. Flintstone lets me work on my own terms, bringing together my technical expertise and creative fluency to build solutions that matter. From small business websites to enterprise process design, each project is grounded in purpose, efficiency, and excellence. Leading Flintstone sharpened my entrepreneurial instincts and deepened my ability to scope, build, and deliver across industries. I've learned how to speak the language of product, brand, and infrastructure - and to operate independently while still driving big outcomes. Through Flintstone, I experiment, stay sharp, and explore innovation with agility.
“Connecting local businesses with their communities.”
The Pop Up App is a passion project and community tool designed to connect local creatives and entrepreneurs through real-time event discovery and storytelling. As product strategist and experience designer, I've led ideation sprints, wireframing, branding, and feature scoping. My goal has always been to build a community-first app experience that prioritizes access, visibility, and authenticity for grassroots creators. In the process, I've collaborated with artists, developers, and event producers to align user needs with digital UX. I've learned about mobile-first architecture, event mapping, and behavioral incentive design - all while shaping a product I deeply care about. This project keeps me rooted in community and design thinking, while building experience in startup-style product development cycles.
“Teaching the next generation of engineers is the ultimate form of leadership.”
At Microsoft, I was tapped to deliver the LEAP program: a high-impact, 16-week global apprenticeship focused on engineering upskilling and equity. In this role, I taught software engineering fundamentals and led global curriculum development in cloud computing, machine learning, cybersecurity, and DevOps. In addition to owning our internal program at Microsoft, I collaborated with public institutions like Chicago Public Schools, corporations like the Chicago Bulls, and international firms like MC Systems in Jamaica to co-develop real-world projects and instructional material. I designed agile learning environments that mimicked professional development cycles and emphasized soft skill growth. Teaching diverse early and mid-career professionals sharpened my ability to break down complex ideas and inspire confidence - a skill I now apply when guiding executives and developers alike. Through this work, I deepened my passion for building high-performance teams by focusing on culture, clarity, and mentorship. I learned how to train for mastery while building a shared language across multi-disciplinary teams.
“Transforming teams and systems through strategic leadership.”
At Rocket Close, I led engineering teams through one of the most transformative eras in the mortgage industry, managing mission-critical software that helped Rocket Mortgage become the #1 lender in the U.S. I joined as a Software Quality Engineer and quickly rose to Software Engineering Manager, building a reputation for leading automation, compliance, and performance engineering initiatives at scale. My teams drove system transitions from legacy on-premise infrastructure to hybrid architectures, while delivering automation that supported record-breaking order volumes during the mortgage boom. I championed cross-functional collaboration between engineering, operations, analytics, and business leadership, building bridges between siloed teams. Through real-time response, strategic delegation, and data-informed decision-making, we maintained regulatory compliance, improved service level agreement (SLA) adherence, and dramatically reduced human touchpoints. I also transformed underperforming teams into some of the highest-performing units in our division by embedding a culture of ownership, curiosity, and collaboration. Most importantly, I learned to lead under pressure - while building and scaling systems, teams, and culture - simultaneously.
“Empowering communities through accessible technical education.”
Dev You was born from a commitment to provide accessible software education ti help bridge the digital divide in Detroit. As a co-founder and lead instructor, I built curricula for early-career and transitioning professionals in Python, C#, Java, javascript and foundational web development. Beyond coding, we taught problem-solving frameworks, architecture fundamentals, and real-world software thinking. I coached students through imposter syndrome, job transitions, and portfolio development - emphasizing not just code, but career confidence. Several alumni from Dev You went on to earn roles in the tech industry. This venture taught me the value of empathy, iteration, and pedagogical design - three traits I now bring into every leadership and transformation role I hold. As a founder and educator, I learned to blend business, community, and technology in impactful ways.
“Creating systems for learning and growth.”
In my first professional role, I served as the Student Life Coordinator at a public charter school on Detroit's westside. This position - akin to a dean of culture - taught me foundational lessons in leadership, empathy, and system-building. I developed student-led programming, facilitated family engagement, and launched cultural initiatives that created a more connected and effective learning environment. Working in a resource-constrained public school pushed me to lead without a budget and to innovate with people, not money. I built lasting relationships with staff, students, and community stakeholders, setting a tone for collaboration and trust that I carry into corporate work today. In that role, I learned that systems, when paired with humanity, can create powerful change. It was my first real taste of leadership, team building, and designing culture with intention.