Location: Chicago, IL – Hybrid
Contract Rate: $80/hr+
We are looking for a senior technical leader who is equally comfortable designing a solution, writing production code, improving delivery pipelines, and helping a team work through difficult technical decisions.
This is a hands-on role for someone who can quickly understand an existing application and team environment, identify where they can add the most value, and help turn ideas into reliable, maintainable solutions. The right person will bring strong .NET and cloud engineering experience, sound architectural judgment, and a genuine interest in using modern development practices and AI-assisted tools to improve how software is designed, built, tested, and operated.
This is not a governance-only or documentation-only architecture role. You will be expected to work directly with engineers, contribute to the codebase and DevOps ecosystem, and help the team deliver quality software.
What You’ll Do
Technical Leadership and Architecture
- Provide hands-on technical leadership across solution design, development, testing, deployment, and production support.
- Design pragmatic solutions that balance business value, technical quality, delivery speed, security, performance, and long-term maintainability.
- Translate business needs and complex problems into clear technical approaches that teams can implement.
- Make thoughtful architecture decisions based on the needs of the product and team rather than defaulting to unnecessary complexity.
- Evaluate tradeoffs, identify technical risks, and help the team make informed decisions.
- Ensure solutions integrate effectively with existing applications, platforms, data, infrastructure, and operational processes.
- Create enough documentation to make decisions, designs, and operational expectations clear without slowing delivery.
Hands-On Engineering
- Contribute directly to application code, infrastructure code, automated tests, delivery pipelines, and technical prototypes.
- Build and support modern applications using .NET and related technologies.
- Review code and designs while providing specific, constructive guidance that helps engineers improve.
- Troubleshoot complex issues across application, integration, infrastructure, deployment, and production environments.
- Improve application reliability, observability, performance, security, and supportability.
- Help reduce unnecessary complexity and technical debt while keeping the team focused on delivering business value.
Cloud and DevOps
- Design, build, and improve solutions running in AWS.
- Develop and maintain infrastructure as code, particularly using AWS CloudFormation.
- Build and improve CI/CD workflows using GitHub Actions.
- Strengthen automated build, test, security, release, and deployment practices.
- Promote repeatable, supportable environments and reduce reliance on manual processes.
- Partner with engineering and operational teams to ensure solutions are production-ready and can be effectively monitored and supported.
AI-Enabled Software Development
- Identify practical opportunities to integrate AI into the software development lifecycle.
- Help the team adopt AI-assisted engineering practices responsibly across design, development, testing, documentation, troubleshooting, and delivery.
- Experiment with new tools and approaches while maintaining appropriate standards for security, quality, privacy, and human review.
- Measure whether new tools and practices are producing meaningful improvements rather than adopting technology for its own sake.
- Share effective approaches with the team and help engineers build confidence using AI as part of their daily work.
Team Leadership and Collaboration
- Join an established team, build trust quickly, and identify where hands-on support will have the greatest impact.
- Collaborate closely with engineers, product partners, business stakeholders, security, infrastructure, and operations teams.
- Communicate complex technical topics clearly to both technical and nontechnical audiences.
- Facilitate technical discussions and help groups move from competing opinions to clear decisions.
- Engage in constructive conflict, challenge assumptions respectfully, and remain open to being challenged.
- Coach engineers through design and implementation decisions without becoming a bottleneck.
- Create an environment where team members can raise concerns, learn from mistakes, and continuously improve.
- Take ownership of outcomes while sharing context, decisions, and knowledge with the broader team.
Required Qualifications
- Significant software engineering experience, including hands-on development of production applications.
- Strong experience with .NET and modern software development practices.
- Hands-on experience designing, building, deploying, and supporting applications in AWS.
- Experience with infrastructure as code, preferably AWS CloudFormation.
- Experience building and maintaining CI/CD pipelines, preferably using GitHub Actions.
- Strong understanding of application architecture, APIs, integrations, data, security, performance, reliability, and observability.
- Experience working across the full software delivery lifecycle, from initial problem definition through production deployment and support.
- Ability to quickly understand unfamiliar systems, codebases, business processes, and team dynamics.
- Demonstrated ability to diagnose complex technical problems and drive them through resolution.
- Strong written and verbal communication skills.
- Ability to give and receive direct, constructive feedback.
- A continuous-learning mindset and a track record of improving both technology and engineering practices.
Preferred Qualifications
- Experience modernizing or incrementally improving legacy applications.
- Experience with distributed systems, event-driven architecture, APIs, and enterprise integration patterns.
- Experience with automated testing, application security, production monitoring, and site reliability practices.
- Experience helping teams adopt AI-assisted development tools or integrate generative AI into engineering workflows.
- Experience operating in complex enterprise environments with multiple systems, stakeholders, and delivery dependencies.
- Experience mentoring senior engineers and developing technical leadership within a team.
- Bachelor’s degree in Computer Science, Engineering, or a related field, or equivalent practical experience.