Senior Software Engineer Jobs in Chicago, IL (NOW HIRING)

As a Senior Software Engineer, you will be involved in all aspects of the design, architecture, engineering, modernization, and maintenance of Roadrunner's proprietary systems. Your focus will be on building scalable, secure, cloud-ready software solutions that improve business efficiency, operational visibility, and customer service.
In this role, you'll own complex, multi-interface technical solutions from concept to delivery, not just contribute to them. You'll partner directly with business stakeholders, analysts, and technology leaders to surface opportunities, assess feasibility, and ship high-quality software. As a senior engineer, you'll lead engineering efforts, set the standard for modern development practices, and operate independently without needing a roadmap handed to you. If you thrive on accountability and technical breadth, this is your seat.
As a Senior Engineer, you will lead the design and implementation of modern software architecture while promoting strong engineering standards, improving development efficiency, and mentoring fellow developers to advance the organization toward cloud-native, API-first, and DevOps-enabled delivery practices. Day to day, you will develop new systems, enhance existing applications, support and optimize the performance of production environments, integrate internal and external platforms, and partner closely with the business to solve operational challenges through technology.What you'll do1. Architect and deliver scalable software solutions

• Design and implement secure, scalable, and cloud-native applications using modern Microsoft technologies
• Apply API-first, modular, and service-oriented architecture principles to platform development
• Lead technical design decisions that align with long-term system scalability and maintainability
• Ensure solutions meet performance, reliability, and business expectations

2. Drive modernization and system evolution

• Lead initiatives to modernize legacy .NET Framework applications through refactoring or cloud migration
• Identify and eliminate technical debt while preserving system stability
• Champion best practices in software architecture, design patterns, and coding standards
• Partner with infrastructure and security teams to align modernization efforts with enterprise strategy

3. Strengthen engineering quality and DevOps maturity

• Promote CI/CD pipelines, automated testing, and secure development practices
• Implement observability strategies, including logging, monitoring, and performance tracking
• Participate in and lead code reviews, ensuring high-quality, maintainable code
• Improve engineering workflows to increase speed without compromising quality

4. Enable cross-functional execution

• Collaborate with product owners, business stakeholders, and analysts to translate requirements into technical solutions
• Communicate complex technical concepts in clear, business-aligned language
• Align engineering deliverables with business priorities, timelines, and operational requirements
• Support production systems and respond to critical incidents with urgency and ownership

5. Lead through technical influence and ownership

• Take ownership of application performance, uptime, and customer impact
• Mentor developers and contribute to the growth of engineering standards and practices
• Drive accountability for outcomes across projects and initiatives
• Contribute to continuous improvement of team processes and technical capabilities

What you bring

• Bachelor's degree in Computer Science, Information Technology, Engineering, or related field (or equivalent experience)
• 5+ years of software development experience within the Microsoft technology stack
• Deep expertise in modern .NET (6/7/8+), ASP.NET Core, Web API, and Entity Framework Core
• Strong experience with ASP.NET MVC, modern front-end frameworks (Angular or React), and TypeScript/JavaScript ecosystems
• Advanced SQL Server expertise, including database design, performance tuning, and query optimization
• Experience designing RESTful APIs, integrations, and service-oriented architectures
• Proven experience developing cloud-native applications, preferably within Microsoft Azure
• Hands-on experience with Azure services such as App Service, Functions, Azure SQL, and Application Insights
• Experience with CI/CD, Git-based source control, and platforms such as Azure DevOps or GitHub Actions
• Strong foundation in application security and secure development practices
• Experience with automated testing, observability, and performance monitoring
• Demonstrated ability to troubleshoot and resolve production issues efficiently

Preferred Qualifications

• Experience in transportation, logistics, freight, or supply chain systems
• Familiarity with Agile, Scrum, or Kanban delivery models
• Experience with API gateways, authentication/authorization, and API lifecycle management
• Track record of modernizing legacy systems through cloud migration or incremental refactoring
• Experience mentoring engineers and shaping engineering standards

How you operate

• You think in systems, not tasks
• You own outcomes, not activity
• You prioritize simplicity, scalability, and long-term maintainability
• You move quickly while maintaining technical discipline
• You challenge assumptions constructively and back decisions with data
• You communicate clearly across both technical and non-technical audiences
• You proactively identify risks and solve problems before they escalate
• You balance autonomy with strong collaboration across teams

About Roadrunner

We're not just moving freight; we're reimagining long-haul shipping. Our Smart Network offers more direct long-haul metro-to-metro routes than any other nationwide LTL carrier in the United States, with service extending into Canada and Mexico and terminals across 40+ metro markets. Powered by AI and machine learning, our operations platform ensures real-time tracking, custodial control, and full shipment visibility. With driver teams executing over-the-road (OTR) moves - and no freight moving on rail - customers experience industry-leading transit times, minimal rehandling, and dramatically reduced risk of loss or damage.

Our 900+ owner-operators benefit from scheduled freight, fewer touches by design, consistent long-haul density, and a differentiated metro-to-metro model that creates predictable earning opportunities.

This precision and performance have earned Roadrunner national recognition by over 3,000 shippers, and was ranked this year #1 in Operations, #1 in Technology, and #1 in Value in the Quest for Quality Awards, as well as honors as a Top 100 Trucking Company by Inbound Logistics and a Top Tier Service Carrier by Mastio.

We're growing fast. Roadrunner is building something special with great people, a winning culture and a differentiated service offering in the marketplace. Join us today to grow your career!

We Run Safe. We Run Smart. We Run Together.

Compensation & Setup

• Pay: $110,000-$130,000 base salary
• Location: Hybrid - Downers Grove, IL
• Benefits: Full benefits package including medical, dental, vision, 401(k), and paid time off
• Travel: Up to 5% travel; occasional after-hours support based on business needs

Physical Demands and Work Environment

The physical demands and work environment described here are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

Physical Demands

• Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
• While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.

Work Environment

• Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
• While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.

* The above statements reflect the general details necessary to describe the principal functions of the position and are not intended to be all inclusive. The position and any of the requirements listed above are subject to change at any time according to the changing needs of the company.

* Roadrunner is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind.

* We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!

#LI-HybridDowners Grove, IL