Full Stack Software Developer
I build and modernize business-critical software, taking projects from business problem and architecture through development, deployment, and production support.
Platform Ownership · Modernization
For more than a decade, I’ve helped build, maintain, and modernize a business-critical property management platform supporting more than 1,200 properties.
My role has grown from full-stack development into primary technical ownership of the platform — working directly with business stakeholders to understand problems, evaluate options and trade-offs, design solutions, and carry them through implementation and production support.
My work spans Java and Spring applications, APIs and integrations, SQL Server, authentication and security, Docker, infrastructure, and cloud architecture. I’m particularly interested in modernizing established systems without adding complexity simply for the sake of using newer technology.
Selected projects that show how I approach modernization, platform ownership, and technical architecture in real production environments.
Modernizing a vulnerable Struts 1 monolith while keeping a business-critical platform running.
Modernized a vulnerable Struts 1 and Java 7 monolith into a maintainable Spring-based platform while continuing to support production and deliver new functionality.
One platform, different users, many workflows, and more than a decade of technical ownership.
More than a decade of building and owning a business-critical platform connecting staff, clients, tenants, vendors, workflows, integrations, and operational processes.
Practical cloud planning grounded in existing workloads, operational requirements, and financial constraints.
Designing a phased AWS migration by assessing existing workloads, right-sizing infrastructure, evaluating architectural trade-offs, and validating decisions through proofs of concept.
Led development of a Swift-based inspection application used in the field to capture property condition information and synchronize completed inspections back to the main platform.
The integrated workflow reduced the time between conducting an inspection and making the resulting report available to clients from days to hours.
Built an Outlook add-in that allows staff to associate emails directly with properties in the management platform.
Email content and metadata are sent through a REST API and stored in the property context, making communication searchable and accessible outside individual staff inboxes.
Additional Microsoft Graph integrations support automated and application-triggered email workflows.
Converted recurring administrative processes into structured digital workflows, including client onboarding, rental applications, templated communications, scheduled tasks and event-driven automation.
Integrated external systems and data including Zoho CRM and MLS information to support communication, reporting and analytics.
Alongside my primary software work, I provide freelance web development for Flynn Group of Companies, building and maintaining public-facing WordPress sites from designs supplied by its marketing team.
Using approved mockups and commercial themes, I customize layouts, responsive behaviour and site functionality for production on WP Engine.
Toronto, Ontario
Responsibility Growth
Software Developer → Senior Software Developer → Primary Technical Ownership
– Present
Primary technical owner of a business-critical property management platform supporting more than 1,200 properties.
Lead application development, modernization, integrations, security, production support and technical planning while working directly with business stakeholders to turn operational needs into software solutions.
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Developed and supported the company’s core property management applications across Java, Spring, SQL Server and web technologies.
Expanded responsibilities over time from feature development and production support into broader application architecture, modernization and platform ownership.
I’m open to senior software development, technical leadership and architecture-focused opportunities where I can combine hands-on engineering with broader ownership of systems and technical direction.
Email: kylemilchard@proton.me
A more personal corner: what I build, play, watch, listen to and obsess over.