Senior Software Engineering Manager – Hybrid (Chicago)

redwoodlogistics; Chicago (IL); Hybrid; USD 180,000 - 220,000; Full time

Benefits offered by this job

Learning & development

Internal mobility

Referral bonus

ERGs

Paid time off

Parental leave

Health benefits

Transit benefit

Disability insurance

Job summary

Redwood Logistics in Chicago is seeking a Senior Software Engineering Manager to lead engineering teams responsible for the Brokerage and Managed Services platforms. You will own engineering execution, delivery predictability, and partner with Product, Architecture, Security, and business stakeholders to deliver reliable, scalable technology solutions that support Redwood's 4PL operating model.

This senior role requires 8+ years of software engineering and 3+ years leadership, with a track

Qualifications

• 8+ years of professional software engineering experience with progression into engineering leadership
• 3+ years leading software engineering teams with accountability for delivery, operational excellence, and people development
• Experience recruiting, developing, retaining, and mentoring engineering talent in a high-performing organization
• Demonstrated experience establishing engineering delivery standards across multiple teams, including release governance, sprint execution, quality practices, and SDLC processes
• Proven track record using engineering performance metrics, including DORA metrics, to improve delivery outcomes
• Experience managing cross-functional delivery across multiple products, platforms, or engineering teams
• Strong software engineering foundation with experience building and operating modern cloud-native applications using C# or comparable technologies
• Experience with public cloud platforms (Azure or AWS), CI/CD pipelines, and modern software delivery practices
• Ability to engage effectively in architecture discussions while providing engineering leadership across multiple teams
• Excellent written and verbal communication skills with the ability to translate technical concepts, delivery status, risks, and tradeoffs into clear, actionable information for executives and business stakeholders
• Demonstrated ability to build trusted partnerships across Product, Architecture, Security, and business leadership to achieve shared outcomes

Responsibilities

• Own engineering planning, roadmap execution, release quality, and predictable delivery against business commitments
• Partner with Product Managers to maintain a healthy, prioritized backlog and ensure engineering input informs roadmap sequencing, estimates, and delivery tradeoffs
• Coordinate cross-team dependencies, proactively manage delivery risks, and remove organizational blockers before they impact commitments
• Forecast engineering capacity and align staffing plans with roadmap priorities, balancing feature delivery, operational work, and technical investments
• Establish and continuously improve engineering standards across the software development lifecycle, including branching strategy, release governance, deployment practices, quality gates, and CI/CD automation
• Partner with Security to implement and continuously improve secure software development practices, including automated code scanning, dependency management, and vulnerability remediation
• Drive engineering quality through modern testing strategies, automation, and continuous improvement of development practices
• Guide technical decision-making by partnering with Architecture and senior engineers to deliver scalable, maintainable, and resilient solutions while reducing technical debt
• Champion engineering practices that promote shared code ownership, knowledge sharing, and reduced reliance on individual contributors
• Own operational excellence for production systems, including availability, incident response, operational readiness, post-incident reviews, and reliability improvements
• Own team-level engineering performance metrics, including DORA metrics, and use data to drive measurable improvements in delivery speed, quality, reliability, and operational maturity
• Balance short-term delivery commitments with long-term platform modernization, scalability, maintainability, and engineering sustainability
• Lead, mentor, and develop high-performing software engineering teams by fostering a culture of accountability, technical excellence, collaboration, and continuous improvement
• Build organizational capability through hiring, onboarding, coaching, structured feedback, performance management, succession planning, and career development
• Establish clear team objectives, define performance expectations, and create an environment where engineers are empowered to grow, innovate, and deliver meaningful business outcomes
• Partner with Product, Architecture, Security, Operations, and business stakeholders to align engineering priorities with company objectives and customer outcomes
• Communicate delivery progress, risks, tradeoffs, and investment recommendations to senior leadership using clear, actionable, and data-driven insights
• Influence engineering strategy by identifying opportunities to improve organizational effectiveness, delivery predictability, platform reliability, and operational efficiency across the technology organization
• Foster strong partnerships across engineering teams to improve execution consistency, organizational scalability, and overall technology health

Skills

Engineering leadership

Delivery leadership

Cloud-native apps

C# or equivalent

CI/CD

DORA metrics

Cross-team coordination

Mentoring

Technical decision making

Operational excellence

Strategic planning

Tools

Azure

AWS

CI/CD pipelines

Job description

Redwood Logistics in Chicago is seeking a Senior Software Engineering Manager to lead engineering teams responsible for the Brokerage and Managed Services platforms. You will own engineering execution, delivery predictability, and partner with Product, Architecture, Security, and business stakeholders to deliver reliable, scalable technology solutions that support Redwood's 4PL operating model.

This senior role requires 8+ years of software engineering and 3+ years leadership, with a track