
Keith Swyer
Verified Expert in Engineering
Software Engineer and Developer
Ottawa, ON, Canada
Toptal member since December 23, 2025
With over 20 years of experience in building and modernizing large-scale distributed systems, Keith combines hands-on engineering with architectural leadership to deliver resilient, high-throughput platforms. His work spans .NET, cloud, data and service boundaries, and AI-augmented development that accelerates delivery. A private pilot who built his own airplane, Keith brings disciplined systems thinking, precision, and curiosity that invite conversation.
Portfolio
Experience
- Microsoft SQL Server - 20 years
- Database Design - 20 years
- Architecture - 20 years
- .NET - 20 years
- Mentorship - 10 years
- PostgreSQL - 10 years
- OpenAI - 5 years
- Claude - 2 years
Preferred Environment
Windows, Git, JetBrains Rider, Microsoft SQL Server, PostgreSQL, React, C#.NET, Docker, .NET, C#, Entity Framework, Debugging, SQL
The most amazing...
...improvements I've done are led by AI-augmented engineering on a product, shrinking refactor cycles and accelerating team delivery.
Work Experience
Principal Software Engineer
Intrahealth - A Healwell AI Company
- Redesigned engineering workflows to an AI-delegation model, breaking complex EMR logic into structured tasks (rules, dependencies, edge cases), reducing multi-day investigations to same-day structured outputs, and accelerating iteration cycles.
- Architected an AI-driven data and testing strategy, analyzing XML schemas and constraint logic to auto-generate high-variance clinical data, increasing edge-case coverage and reducing reliance on manually curated test datasets.
- Operationalized AI development tooling across teams, piloting AI coding, PR, and automation workflows with rapid evaluation and rollout (idea-to-license in around one hour), increasing experimentation velocity and reducing delivery friction.
Back-end Engineering Technical Lead
Deck
- Led the .NET back-end engineering team, driving major architectural, API, and database improvements that significantly increased system performance, scalability, and reliability.
- Scaled the platform from an early-stage startup system to a robust back end capable of supporting 250,000+ requests per day with predictable performance and stability.
- Established patterns and guidelines for distributed concurrency, workload orchestration, API resiliency, and fault-tolerant service communication.
- Acted as the organization’s leader in applied AI engineering—guiding strategic adoption of coding assistants, establishing safe-use practices, and implementing workflows that enhanced code quality, velocity, and developer productivity.
- Championed advanced AI-driven development techniques such as context engineering, prompting strategies, and automated code analysis—helping the team leverage AI as a force multiplier rather than a hindrance.
- Mentored engineers on effective AI tooling integration, ensuring safeguards, reproducibility, and technical correctness while accelerating development across back-end and scraper teams.
Software Engineering Lead
RVezy
- Upgraded from Entity Framework (EF) Core 2 to EF Core 3, followed by a move to EF Core 7. This was a significant undertaking due to the complexities of client-side vs. server-side queries, which were exposed in EF Core 3.
- Merged six microservices into a single project. Improved developer experience and maintainability and reduced complexities and overhead, achieving faster API responses, improved testability, and significant improvements to deployments and resources.
- Merged the two main systems and databases to reduce unnecessarily complex logic, simplify developer experience and maintainability, and allow ACID transactions, dropping the number of orphaned records to zero.
- Designed and set up API-level integration tests and frameworks that allowed for fully idempotent tests—enabling us to find and fix existing bugs faster by creating the test first to duplicate the issues in a repeatable way.
- Mentored and helped lead a small team of developers working to help them reach their professional and personal goals.
- Provided a migration path from older, slower, and far less reliable Selenium end-to-end testing to a more robust and reliable design using Playwright.
Senior Software Engineer
Rotabull
- Worked on back-end solutions in Elixir and .NET and contributed to infrastructure design.
- Led the integration of customer database systems on a one-by-one basis to synchronize with our database systems.
- Mentored a small, young, talented group of engineers into a keep-it-simple mindset.
Director of Engineering
Portal
- Led design from concept to full-blown project, scaling to millions of transactions.
- Implemented real-time search of millions of products and specifications, customized to each user.
- Implemented a large data ingestion system, providing custom pricing on a per-user basis.
Experience
Deck.co
http://www.deck.co/Deck turns login-gated websites into structured, programmatically accessible data through intelligent agents that handle authentication, session management, navigation, and extraction at scale—enabling read and write operations where APIs don’t exist. The platform powers integrations for real-time utility, eCommerce, ERP, telco, and other account data with robust job orchestration, normalization, and developer workflows that simplify complex, brittle automation into reliable, auditable outputs.
Deck’s infrastructure enables engineering teams to rapidly connect customer accounts and build data-driven features with significantly less custom code and maintenance overhead than traditional browser automation or scraping.
My Flight Deck
http://www.myflightdeck.ca/Architected on scalable services with strong data integrity guarantees, My Flight Deck supports multi-aircraft ownership, role-based access, and auditable records suitable for real-world inspections. AI is integrated not as a novelty, but as a productivity layer—accelerating document review, maintenance interpretation, and data reconciliation while keeping humans in control. Built by a pilot and aircraft builder, My Flight Deck reflects deep domain knowledge, disciplined systems thinking, and a focus on correctness, performance, and trust.
Airfield Guide
https://airfieldguide.caThe platform allows users to browse airfields on an interactive map, view details such as runway surface, length, condition, photos, notes, and operational considerations, and contribute their own updates. The goal is to build a continuously improving, user-maintained database similar in concept to AllTrails, but for aviation.
In addition to airfield discovery, the long-term vision includes community features, aircraft owner tools, and maintenance or flight-logging integrations, with an emphasis on simplicity and usability for general aviation pilots, including older users who prefer clear and straightforward interfaces.
Education
Bachelor's Degree in Software Engineering
University of Western Ontario - London, Ontario, Canada
Skills
Libraries/APIs
OpenAI API, Entity Framework, Stripe, REST APIs, Stripe API, React, Claude API, Node.js
Tools
Claude, AI SDK, Claude Code, ChatGPT, Git, RabbitMQ, Terraform, Microsoft Copilot, JetBrains Rider, n8n, Claude Agent SDK
Languages
C#, SQL, Python, TypeScript, C#.NET, Elixir
Frameworks
.NET, Swagger, ASP.NET Core, Blazor, LangGraph, MassTransit, ServiceStack, Angular, Next.js, Tailwind CSS, LlamaIndex
Paradigms
Database Design, DevOps, REST
Platforms
Windows, Vercel, Azure, Amazon Web Services (AWS), Docker, Oracle, Algolia, Langfuse, Clerk
Storage
Microsoft SQL Server, PostgreSQL, Redis, Databases, NoSQL
Other
OpenAI, RESTFul APIs, Architecture, Mentorship, Team Leadership, APIs, System Architecture, API Integration, Debugging, Data Processing, Reverse Engineering, System Integration, Artificial Intelligence (AI), Development, AI Integration, Full-stack Development, AI Agents, AI Chatbots, Solution Architecture, Generative Artificial Intelligence (GenAI), Full-stack, Workflow Automation, .NET 10, Anthropic, Prompt Engineering, Enterprise SaaS, OAuth, Message Queues, Distributed Systems, Message Bus, Large Language Models (LLMs), Payment Gateways, CI/CD Pipelines, Cloud Infrastructure, RAG Architecture, Retrieval-augmented Generation (RAG), eCommerce, LangChain, Agentic AI, Agentic RAG Systems, AI Architecture, Vector Databases, Azure Stack, Cloud Architecture, Software Engineering, Cloud, Machine Vision, Large Data Sets, Document Processing, Data Extraction, Leadership, Integration, Search, Supabase, Supabase Auth, Lemon Squeezy, Electronic Medical Records (EMR)
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