Senior Software Engineering Manager Jobs in Chicago, IL

Senior Software Engineering Manager

Reports To: Chief Technology Officer (CTO)

Location: Chicago, IL

Environment: Hybrid (3 days onsite/week)

Status: Exempt; Salaried

Who We Are:

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.

Purpose of Your Work:

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.

How You Make a Difference Everyday:

• 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.

You’ve Got This?

• 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 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

What We Offer:

• Access to experts and resources for your Learning & Development journey
• Opportunity for internal mobility
• Employee referral bonus program
• Employee Resource Groups (ERGs)
• Annual fundraising and volunteer events to give back to communities
• Paid time off, floating holidays, time off to volunteer and rollover
• Paid parental leave
• Medical, dental, vision and 401k plans (with match)
• Flexible spending account, mass transit and dependent care plans available
• Health savings account, with a annual company contribution for plan participants
• Short-term and long-term disability; life insurance policies subsidized by company
• Additional benefits including pet insurance, accident care, access to legal advice and more

Work Schedule:

This position is full-time and hybrid Monday through Friday from 8:00 AM to 5:00 PM with an hour break, but flexibility is available based on coverage.

Compensation Range:

Salary Range:

$180,000 - $220,000

This position is eligible to earn annual incentives based on individual and company performance.

The estimated pay range reflects an anticipated range for this position. The actual base salary offered will depend on a variety of factors, including the qualifications of the individual applicant for the position, years of relevant experience, specific and unique skills, level of education attained, certifications or other professional licenses held, and the geographical location in which the applicant lives and/or which they will be performing the job.

Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit, qualifications, abilities, and the Company’s needs and resources. The Company does not discriminate in recruiting, hiring, compensation, promotions, discipline, termination or any other aspect of employment on the basis of an individual’s actual or perceived race, color, creed, religion, sex (including pregnancy, childbirth and related medical conditions), sexual orientation, gender identity, national origin, ancestry, citizenship status, age, disability, marital status, military service or status, genetic information, arrest and conviction record, credit history, or any other basis protected by applicable law.