Sr. Software Engineer

About the Role

We are seeking a Senior Software Engineer with deep expertise in Windows engineering to lead the migration of diverse Windows-based workloads—including homegrown applications, COTS products, and legacy services—into modern AWS-hosted environments. As a Cloud Migration Engineer, you will be instrumental in designing test plans, validating application behavior, externalizing configurations, and troubleshooting migration challenges. Your role ensures migrated applications are reliable, supportable, and aligned with enterprise standards.

Key Responsibilities

• Test Plan Development & Execution: Create and implement detailed test plans for Windows workloads, covering COTS applications, IIS/.NET services, Windows services, scheduled tasks, and SQL-connected systems. Validate functionality, configuration, networking, authentication, and performance in AWS.
• Migration Execution & Support: Lead hands-on migration efforts, including installation validation, connectivity testing, functional smoke tests, configuration extraction, and issue resolution (e.g., registry keys, service identities, permissions, certificate stores, firewall rules, DNS, authentication).
• Team Mentorship & Knowledge Sharing: Educate and coach application teams on remediating environment differences, redesigning configuration models for portability, and adopting cloud-aligned operational best practices.
• Automation & Consistency: Develop scripts, runbooks, and repeatable validation steps to address common Windows migration challenges (e.g., missing dependencies, blocked ports, legacy configuration paths, registry drift).
• Cross-Functional Collaboration: Partner with infrastructure, security, and network teams to align migration prerequisites, resolve systemic issues, and standardize practices for identity, logging, monitoring, access, and AMI lifecycle.
• Problem Solving: Independently resolve complex technical issues with minimal supervision, escalating only the most systemic challenges.

Qualifications

Minimum Requirements

• Bachelor’s degree in a related field (or equivalent experience).
• Proven experience troubleshooting Windows Server environments, including application services, configuration management, SQL connectivity, certificate stores, and Active Directory integration.
• Hands-on experience supporting cloud-hosted Windows workloads (AWS, Azure, or similar).
• Expertise in diagnosing network issues (firewall rules, security groups, DNS, routing, port-level connectivity).
• Minimum of 4 years of related work experience.

Preferred Qualifications

• Experience migrating COTS applications to AWS, including handling installers, licensing models, and vendor-defined configurations.
• Proficiency with Windows diagnostic tools (Event Viewer, PerfMon, Resource Monitor, Services MMC, Registry Editor, IIS Manager) and network troubleshooting tools (netsh, Test-NetConnection, nslookup, PowerShell networking utilities).
• Ability to analyze AWS networking constructs to resolve connectivity and hybrid networking issues.
• Skills in establishing monitoring, logging, and observability practices for post-migration reliability.
• Expertise in PowerShell for automation, diagnostics, and configuration extraction.
• Experience resolving migration blockers such as hardcoded paths, registry-only configurations, licensing constraints, and legacy authentication challenges.