Software Engineer, Modernization

Origami Risk delivers SaaS solutions for risk, insurance, compliance, and safety management. The Software Engineer, Modernization will reduce technical debt, modernize legacy .NET and C# applications, and re-platform systems onto cloud-native AWS architectures using AI-assisted development tools. The role also involves establishing engineering standards, collaborating across teams, and supporting scalable, maintainable product delivery.

Responsibilities:

• Systematically identifies, prioritizes, and remediates technical debt across existing codebases, partnering with Engineering Leads to build and execute a structured modernization backlog
• Refactors and re-platforms legacy .NET and C# applications onto modern, cloud-native architectures - improving maintainability, performance, and scalability without disrupting active product delivery
• Decomposes monolithic systems into clean, loosely-coupled microservices and APIs, establishing clear domain boundaries and reducing interdependencies that slow delivery velocity
• Replaces brittle, over-engineered, or redundant systems with simpler, more sustainable solutions that are easier to understand, test, and evolve
• Uses AI-assisted tooling (e.g., Claude Code, Cursor, GitHub Copilot) to analyze legacy code at scale - accelerating impact analysis, generating refactoring candidates, and producing documentation for undocumented systems
• Migrates workloads from legacy infrastructure to cloud-native patterns on AWS, leveraging Lambda, containers (ECS/EKS), Step Functions, Temporal, and managed services to reduce operational overhead and improve scalability
• Applies modern software design patterns - including event-driven architecture, CQRS, and domain-driven design - to re-architected systems, positioning them to support future innovation and client scale
• Implements database migration and schema modernization using Flyway, ensuring safe, versioned transitions away from legacy data models
• Builds containerized services using Docker, establishing consistent deployment and runtime environments across development, staging, and production
• Authors infrastructure-as-code using Terraform or AWS CDK to replace manual, brittle environment configurations with repeatable, auditable provisioning
• Champions engineering simplicity as a first-class design principle - pushing back on unnecessary complexity and advocating for solutions that are easy for the next Engineer to understand and change
• Establishes and documents patterns for modernized systems, creating reusable blueprints that accelerate future re-platforming efforts and provide a consistent architecture baseline across the Engineering organization
• Instruments modernized systems with observability best practices - structured logging, distributed tracing, and metrics - so that operational visibility improves alongside code quality
• Contributes to and enforce Engineering standards around code quality, testing, documentation, and API design, ensuring modernized systems raise the bar rather than just moving problems
• Designs modernized systems with client scale in mind - ensuring they can support increased load, faster release cadences, and rapid product iteration as the business grows
• Actively integrates AI development tools into your daily workflow to accelerate refactoring, generate test coverage for legacy code, and produce migration documentation
• Uses AI to perform large-scale codebase analysis - identifying duplication, dead code, anti-patterns, and high-risk areas across legacy systems that would take weeks to assess manually
• Partners with the AI Platform & Backend Services team to identify modernization opportunities that can be unlocked by new AI-powered capabilities
• Contributes to team best practices around responsible and effective use of AI-assisted development, sharing techniques that improve team-wide velocity and code quality
• Works closely with Engineering Managers, Architects, and Product teams to sequence modernization work alongside active feature development, minimizing disruption to product delivery
• Participates in architecture reviews and design discussions, bringing a modernization lens to new initiatives to prevent the introduction of new technical debt
• Contributes to pull request reviews with a focus on simplicity, maintainability, and alignment with modernization standards
• Collaborates with QA, Security, and Infrastructure teams to ensure modernized systems meet quality, compliance, and performance requirements
• Documents architectural decisions, migration patterns, and system changes to build institutional knowledge and reduce dependency on tribal knowledge

Requirements:

• • Bachelor's Degree in Computer Science, Software Engineering, Information Systems, or a related field
• • 3+ years of professional software engineering experience, including demonstrated work on legacy modernization, refactoring, or re-platforming initiatives
• • Proficiency in .NET and C#, with experience working in both legacy and modern application codebases
• • Solid understanding of software design principles including SOLID, clean architecture, domain-driven design, and separation of concerns
• • Experience designing and building RESTful APIs and microservices, with strong instincts for clean, consumer-friendly API contracts
• • Hands-on experience with cloud-native development on AWS, including one or more of: Lambda, Step Functions, ECS/EKS, API Gateway, SQS/SNS
• • Familiarity with containerization using Docker and deployment in containerized environments
• • Experience with version control and collaborative development workflows using Git and GitHub
• • A demonstrated ability to communicate about technical complexity clearly — to both technical peers and non-technical stakeholders
• • Experience with AI-assisted development tools such as Claude Code, Cursor, or GitHub Copilot, including using AI for codebase analysis and refactoring acceleration
• • Familiarity with workflow orchestration using Temporal or AWS Step Functions in a production environment
• • Experience with database migration tooling such as Flyway and safe schema evolution practices
• • Experience with infrastructure-as-code tooling (Terraform, AWS CDK, or Pulumi)
• • Familiarity with event-driven architecture patterns and asynchronous messaging (SQS, SNS, EventBridge, or Kafka)
• • Experience working in an Agile/Scrum development environment
• • A strong personal conviction that simple, well-structured systems are a competitive advantage — and a track record of building them