Senior Software Engineering Manager

Current job opportunities are posted here as they become available.

Reports To:

Chief Technology Officer (CTO)

Location:

Chicago, IL

Environment:
Hybrid (3 days onsite/week)

Recognized by Gartner in their Modern 4PL Market Guide, Redwood Logistics is at the forefront of industry innovation. Our cutting-edge supply chain technology pairs with the expertise of our brilliant minds to empower logistics execution across North America and Mexico.

Leveraging a comprehensive range of services, data-centric network solutions, and a seamlessly integrated platform, we have established our prominence as a key player in the mid-market segment within the freight tech industry.

Whether you’re just starting your career or are an established professional looking for your next opportunity, Redwood inspires innovation across teams to provide transformative solutions for our customers.

As a Senior Software Engineering Manager within Redwood's Technology organization, you will lead engineering teams responsible for the Brokerage and Managed Services platforms. You will own engineering execution, operational excellence, and delivery predictability while developing engineering talent and partnering across Product, Architecture, Security, and business stakeholders to deliver reliable, scalable technology solutions that support Redwood's 4PL operating model.

• 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.

• 8+ years of professional software engineering experience with demonstrated 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…