Jonathon O'Reilly
Innovation is Connection
Technology Architect | Building scalable solutions that connect people with innovation and empower them to achieve more
My Story
From building K'NEX carnivals to architecting enterprise systems
I grew up in the Dallas Metroplex with my hands always busy—whether I was building elaborate carnivals out of K'NEX or helping my dad tackle house projects. Those early experiences taught me something fundamental: the joy of building, of taking an idea and making it real.
My journey into technology began in high school, but it truly clicked in college when I took a C++ programming class as an elective. As a mathematics major, programming felt like a natural extension of the problem-solving I loved. But more than that, it brought back that same joy of building I'd felt as a kid—only now, I was creating digital systems instead of physical ones.
What truly drives me is building the internal processes and technology stacks that make automation easier and empower others to excel at their jobs. Whether it's deploying an AI chatbot to support customer service teams, designing a product information management system that streamlines vendor onboarding, or leading the development of a company-wide data warehouse that enables data-driven decisions across 80+ employees—I'm most proud of creating technology that makes people's days easier.
I recently completed my master's degree in software engineering at Harvard Extension School, where I focused on AI-driven home security in IoT environments. This research deepened my understanding of balancing innovation with security and risk management, perspectives that continue to influence how I architect enterprise systems today.
At my core, I see myself as someone who connects people with innovation. Technology isn't just about code and infrastructure—it's about empowering teams to do their jobs better and helping organizations achieve their common goals. That's what gets me excited about what I do every day.
Over 12+ years, I've had the privilege of advancing through progressive technology roles at Christianbook, helping the company grow 3x in revenue. But revenue numbers only tell part of the story.
Areas of Expertise
12+ years building enterprise systems that scale
Technology Strategy
- Enterprise-scale web architecture
- Microservices transformation
- API-first design
- Architecture governance
- Cloud solutions (Azure & AWS)
AI & Innovation
- AI-enabled development
- GenAI business integration
- AI-powered customer support
- IoT security & threat detection
- Emerging technology adoption
Full Stack Development
- JavaScript/TypeScript, Python, Java
- React, Node.js, React Native
- Postgres, MySQL, Neo4j, MongoDB
- Event-driven architecture
- DevOps & CI/CD pipelines
eCommerce & Growth
- eCommerce platform optimization
- PCI compliance & security
- Performance & scalability
- Attribution modeling
- Revenue-driving technology
Data & Analytics
- Data warehouse architecture
- Business intelligence solutions
- Analytics & reporting platforms
- Product information management
- Data-driven decision support
Leadership & People
- Cross-functional team leadership
- Mentoring & coaching
- Stakeholder collaboration
- Agile methodologies
- Product ownership
My Superpower: Bridging Technical & Business Worlds
I have a unique ability to listen deeply to both technical implementors and executive teams, translating complex technical concepts into business value. I don't just hear concerns—I understand them from multiple perspectives, enabling me to architect solutions that serve everyone from developers to C-suite leaders. I get most excited solving problems that make people's days easier, whether that's helping consumers find what they need or empowering employees with better tools to excel at their work.
Career Journey
Key milestones in my professional evolution
Web Developer at Christianbook
Started my journey building secure internal systems, SEO-optimized components, and user-driven enhancements for a growing eCommerce platform.
Promoted to Senior Web & Full Stack Developer
Led critical web projects including payment integration redesign, page optimization that cut response times by 2 seconds, and implementation of centralized logging with Elastic Stack.
Promoted to Web Architect
Advanced to enterprise architecture role, leading transformative initiatives including microservices migration, AI chatbot deployment, and development of custom product information management platform.
Completed Master's Degree
Earned Master of Liberal Arts in Software Engineering from Harvard Extension School, focusing on AI-driven home security in IoT environments using graph databases and passive threat detection.
Mobile App Modernization
Consolidated 2 native eReader codebases into unified React Native platform, achieving feature parity and 20% increase in user retention post-launch.
Attribution Modeling
Built fractional order attribution system, enabling executives to track KPIs and align departmental budgets with company-wide sales goals.
Azure Data Warehouse Launch
Led hybrid team of 13 to deliver Azure Synapse data warehouse in 6 months, enabling data-driven decisions across 80+ business users company-wide.
Exploring Next Chapter
Continuing to learn about Generative AI's impact on business processes while seeking opportunities to connect people with innovation at scale.
Core Values
The principles that guide my work
Keep It Simple
Complexity is easy; simplicity is hard. I believe the best solutions are elegant and straightforward, cutting through noise to deliver what truly matters. Simple systems are maintainable, scalable, and empower teams to move faster.
Ask Questions
Curiosity drives innovation. I approach every problem by asking questions—understanding the "why" behind requirements, uncovering hidden constraints, and ensuring alignment between technical solutions and business goals. The best architectures emerge from deep understanding.
Keep Learning
Technology never stands still, and neither should we. I'm committed to continuous growth—whether that's exploring Generative AI, studying new architectural patterns, or learning from the brilliant people I work with. Every project is an opportunity to expand my understanding.
My Philosophy: Innovation is Connection
I see myself as someone who connects people with innovation to ultimately help them do their jobs better and forward common goals. Technology exists to serve people—whether that's building platforms that enable consumers to easily find and purchase what they need, or architecting systems that make employees' work more efficient and meaningful. The best innovations aren't just technically sophisticated; they're bridges that connect human needs with technological possibilities. When we get that connection right, everyone wins.
Beyond the Code
What I'm passionate about outside of work
Audiobook Enthusiast
I'm an avid listener of audiobooks, constantly exploring new ideas and perspectives. Recently, I've been diving deep into AI Leadership, which has shaped my thinking on how to responsibly integrate emerging technologies into business strategy.
Home Projects & Building
That childhood love of building never left. I enjoy tackling home projects—from constructing outdoor stairs to various DIY improvements. There's something deeply satisfying about creating functional, tangible things with your hands that mirrors the work I do in the digital realm.
Generative AI & Business Innovation
I'm currently immersed in learning how Generative AI can transform business processes. This isn't just academic curiosity—I'm actively exploring how to help organizations leverage AI responsibly to improve operations, enhance customer experiences, and create new value.
Let's Build Something Together
Let's Build Something Together
Interested in connecting innovation with impact? I'd love to hear about your challenges and explore how we can work together.