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JONATHON O’REILLY

Boston, MA

Accomplished Website Architect | Principal Engineer | Growth-Focused Technology Strategy Leader

AREAS OF EXPERTISE


✓ Technology Strategy
✓ Full Stack Web Development
✓ Azure & AWS Cloud Solutions
✓ Data Warehousing
✓ AI-Enabled Development
✓ API-First Design
✓ Architecture Governance
✓ Web Security Standards
✓ Regulatory Compliance
✓ eCommerce Platforms
✓ Event-Driven Architecture
✓ Project Management
✓ Agile Methodologies
✓ People Leadership
✓ Product Ownership
✓ Mentoring & Coaching

CAREER HIGHLIGHTS


  • Web Architecture: 12+ years of progressive web development experience, leading IT and web strategy for a national 9-figure business.
  • IT Leadership: Led strategy and execution for the development of GenAI solutions, eReader Applications, data warehouses and more.
  • Revenue Growth: Played a key technical role enabling Christianbook to expand from $100M in revenue to over $300M over 10 years.
  • AI Security: Recently completed a master’s degree in software engineering with a focus on AI-based home security in the IoT space.

Skills & Expertise

Coding Languages

  • JavaScript/Typescript
  • SQL
  • Perl
  • Python
  • Java
  • HTML/CSS

Databases

  • Postgres
  • MySQL
  • Oracle
  • Elasticsearch
  • Redis
  • Neo4j
  • MongoDB

Technology

  • Node.js
  • React (Remix/NextJS Frameworks)
  • React Native
  • JQuery
  • Django

Other

  • Azure
  • AWS
  • Supabase
  • Google Analytics
  • Akamai Platform
  • Gitlab/Github
  • Linux/Unix

Work Experience

Web Architect

ChristianbookFull-time
Current
Jan 2019 - Present(6 years, 11 months)
Boston, MA

Promoted into this senior architecture role at the large online retailer, holding accountability for leading enterprise-scale web and data initiatives, managing cross-functional teams and vendors, and shaping technology strategy in collaboration with executives.

  • AI Integration: Deployed an AI chatbot to handle level 1 and 2 support, reducing customer service workload while improving response time and consistency. Partnered with stakeholders to ensure adoption and performance of this new AI solution.

  • Platform Development: Directed a 3-person team to design and launch a product information management system in 4 months, streamlining vendor onboarding and enabling 10+ publishers to self-manage product data with improved accuracy.

  • Cloud Data Strategy: Led a hybrid team of 5 staff and 8 consultants to deliver an Azure Synapse data warehouse in 6 months, completing knowledge transfer within 9 months, and rolled out Power BI dashboards to 80+ business users company-wide.

  • Attribution Modeling: Built a fractional order attribution system applying time decay and last-touch models, collaborating with executives to track KPIs, align departmental budgets, and monitor company-wide sales goals across all business units.

  • Architecture Transformation: Spearheaded migration from monolith to microservices, designing NodeJS APIs and integrating Akamai CDN, resulting in 10% offload of requests while enhancing scalability, security, and performance across 40 websites.

  • DevOps Acceleration: Introduced GitLab SCM and CI/CD pipelines, cutting deployment cycles from 4 weeks to 1 week while ensuring safe, transparent, and traceable processes that improved developer productivity and operational reliability.

  • Mobile App Modernization: Consolidated 2 native eReader codebases into a React Native platform for both iOS and Android, managing 4 team members. Completed this project to achieve feature parity and a 20% increase in user retention post-launch.

  • Leadership & Mentoring: Managed external consultants and 4-5 interns each year, guiding projects, instilling best practices, and supporting career growth. Mentoring highlight came when one intern/mentee was promoted to a senior engineer role.

  • Enterprise Training: Conducted training sessions for 80+ employees on data warehouse usage and analytics tools, driving adoption across departments and enabling data-informed decision-making that supported company-wide objectives.

Senior Web & Full Stack Developer

ChristianbookFull-time
Jan 2015 - Jan 2019(4 years, 1 month)
Boston, MA

Promoted into a senior development role to own critical web projects, integrate external vendor platforms, and lead redesigns that improved performance, security, and scalability across high-traffic eCommerce operations.

  • Payment Integration: Designed and maintained Chase Paymentech integration in Java to securely process millions of transactions across 70+ websites, ensuring compliance, reliability, and scalability in high-volume eCommerce operations.

  • Page Redesign: Led developers in redesigning product pages with responsive practices and performance enhancements, cutting average response times by 2 seconds and creating a faster, more engaging customer experience.

  • Web Crawlers: Built multiple NodeJS and Python-based crawlers to access external sites, automatically retrieving updated product and pricing data, reducing overhead costs and improving margin visibility across critical product categories.

  • Logging & Monitoring: Collaborated with management and system engineers to centralize log collection using Elastic Stack, enabling automated monitoring and real-time alerts that accelerated resolution of network issues and improved stability.

  • Mentorship: Coached new hires in development practices and team integration, ensuring faster ramp-up and improved longterm contributions to the development team’s success.

Web Developer

ChristianbookFull-time
Jul 2013 - Jan 2015(1 year, 6 months)
Boston, MA

Joined as a developer to design secure internal systems, build SEO-optimized web components, and deliver user-driven enhancements that improved site functionality and streamlined daily operations in support of eCommerce growth.

  • Admin System: Built an admin application integrated with Active Directory, enabling role-based security and streamlining onboarding for 100+ employees, ensuring secure access control and daily operational efficiency across the organization.

  • SEO Enhancements: Developed SEO-optimized and responsive web components integrated with the CMS, improving discoverability and user experience while supporting traffic growth and strengthening the retailer’s online presence.

  • User Collaboration: Partnered with key business users to gather feedback on site features and admin interfaces, implementing object-oriented design solutions that improved usability, reduced pain points, and strengthened stakeholder engagement.

  • SDLC Participation: Supported all phases of the software development lifecycle, from requirements gathering through testing and release, ensuring timely delivery of features and ongoing enhancements to enterprise eCommerce systems.

  • Team Contribution: Collaborated with engineers across multiple disciplines to deliver reliable and secure solutions, applying coding best practices and knowledge sharing that reinforced technical quality and team cohesion.

  • Web Development: Designed and implemented front-end and back-end functionality across eCommerce websites, ensuring scalable performance and responsive design standards that strengthened customer engagement and conversion rates.

  • System Support: Maintained and enhanced existing web tools and services, ensuring stability, resolving defects, and implementing improvements that optimized performance and reliability for end-users and internal stakeholders.

Education

Bachelor of Arts in Mathematics (minor in Computer Science)

Master of Liberal Arts in Software Engineering

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