Middle Software Engineer, Modernization

The Software Engineer, Modernization is at the center of our modernization effort: systematically identifying and eliminating technical debt, re-platforming legacy systems onto clean, cloud-native architectures, and building solutions that are built to last. This person leverages AI heavily throughout their workflow — using it to accelerate analysis, generate refactored code, and uncover patterns across large legacy codebases.

Starting base pay for this role is between $97,000 and $122,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states).

Technical Debt Reduction & Legacy Modernization

• 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.

Cloud-Native Re-platforming

• 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.

Standards, Simplicity & Scalability

• 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.

AI-Augmented Development

• 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.

Collaboration & Delivery

• 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.

• 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

Preferred Qualification:

• 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

• Medical and Dental coverage available for employees, dependents, domestic partners, and spouses
• Paid Time Off – Flexible options plus 10 paid company holidays where available**
• All full-time positions are hybrid, with many eligible to be completely remote
• Fully Paid by Origami Risk – Vision insurance, Short & Long-Term Disability Insurance, and Basic Life Insurance
• Generous family leave options—including adoption and foster care placements
• Pre-Tax Savings Accounts – Flexible Spending Account, Health Savings Account, Commuter Benefits, Dependent Care Savings Account
• Retirement Savings – 401(k) with company match up to 4%
• Employee Assistance Program (EAP) – Confidential & Free support offered to colleagues facing personal or work-related complications
• Education Assistance Program – to help colleagues pursue industry/role-specific certifications
• Wellness Benefits – reimbursement program to invest in healthy habits as well as support better colleague productivity and stress management
• Additional coverages available – Pet Insurance, Critical Illness Insurance, and Voluntary Life & AD&D coverage

Origami Risk delivers single-platform SaaS solutions that help organizations best navigate the complexities of risk, insurance, compliance, and safety management.

Founded by industry veterans who recognized the need for risk management technology that was more configurable, intuitive, and scalable, Origami continues to add to its innovative product offerings for managing both insurable and uninsurable risk; facilitating compliance; improving safety; and helping insurers, MGAs, TPAs, and brokers provide enhanced services that drive results.

A singular focus on client success underlies Origami’s approach to developing, implementing, and supporting our award-winning software solutions. 

Origami Risk is proud to be an equal opportunity employer. We thrive and benefit from diversity and are committed to creating an inclusive and equitable environment for all employees. We do not discriminate against any individual based upon race, religion, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, color, sex, national origin, age, marital status, military or veteran status, disability, or any other characteristic protected by applicable law.