Vice President of Engineering

Vice President of Engineering

Reports To: Chief Technology Officer

Location: Remote (within the U.S.)

Environment: Remote

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:

Redwood Logistics is seeking a Vice President of Engineering to lead the engineering organization responsible for building and operating our core technology platforms. Reporting directly to the CTO, the role owns the full engineering function: hiring and developing engineering talent, setting delivery standards, driving architectural quality, and shipping software that powers our brokerage operations, TMS platform, and customer-facing products.

You will be expected to stay close to the technical work, setting architectural direction, unblocking teams, and holding a high bar for quality and reliability, while also managing and growing a team of engineering managers and senior engineers. You will partner tightly with Product, Data/AI, and Operations to turn roadmap commitments into production systems.

The ideal candidate brings deep engineering credibility, a strong track record of scaling software teams in high-growth environments, and the operational discipline to run an engineering org that ships quickly and confidently.

How You Make a Difference Everyday:

Engineering Leadership & Team Development

• Lead, grow, and retain a team of engineering managers, senior engineers, and individual contributors across product engineering, platform, DevOps, and QA.

• Set a high bar for engineering quality, code review, and technical craftsmanship across all teams.

• Build and manage a healthy engineering culture grounded in psychological safety, accountability, continuous learning, and pride in craft.

• Establish clear career ladders, performance frameworks, and promotion criteria for the engineering organization.

• Drive active recruiting efforts to attract top engineering talent; own headcount planning and org design in partnership with the CTO and HR.

Software Delivery & Execution

• Own the end-to-end software delivery process, planning, sprint execution, release management, and post-launch operations.

• Partner with Product leadership to translate roadmap priorities into well-scoped engineering projects with clear timelines and resource plans.

• Drive delivery predictability, establishing engineering metrics (cycle time, deployment frequency, defect rates, incident response) and holding teams accountable to them.

• Lead the engineering organization through competing priorities, ambiguity, and rapid growth without sacrificing quality or team health.

• Own the engineering components of major product launches: readiness reviews, rollout plans, monitoring, and post-launch retrospectives.

Architecture & Technical Direction

• Define and enforce architectural standards across Redwood's software systems, microservices, APIs, data pipelines, and integrations.

• Drive ongoing technical debt reduction, system scalability initiatives, and modernization of legacy components.

• Establish and govern engineering design review processes for significant new systems or changes.

• Partner with the CDAIO to ensure data and AI infrastructure integrates cleanly with product engineering systems.

• Make build-vs-buy-vs-integrate decisions in partnership with the CTO and Product leadership.

Platform Reliability & Operations

• Own the reliability, availability, and performance of Redwood's production systems, SLAs, incident management, on-call rotations, and post-mortems.

• Drive a culture of operational excellence: proactive monitoring, alerting, capacity planning, and zero-downtime deployments.

• Oversee the DevOps and infrastructure engineering function, ensuring CI/CD pipelines, cloud infrastructure, and deployment tooling meet the demands of a fast-moving product organization.

• Ensure security and compliance are embedded in the SDLC, SOC 2, data privacy, and access control requirements built in, not bolted on.

Cross-Functional Partnership

• Serve as the primary engineering partner to the Head of Product, translating roadmap priorities into delivery plans, surfacing trade-offs, and aligning on scope and timelines.

• Collaborate with the Head of Data to ensure platform interoperability and shared infrastructure standards.

• Partner with Finance and Operations to manage the engineering budget, vendor contracts, and cloud cost optimization.

• Represent engineering in executive forums, communicating delivery status, risks, and investment needs to the CTO and broader leadership team.

You’ve Got This?

Required

• 12+ years of software engineering experience, with 5+ years in engineering leadership roles managing teams of 30+ engineers across multiple product areas.

• Proven track record shipping complex, high-availability B2B or enterprise software systems at scale.

• Strong technical depth: able to engage credibly in system design, code review, architectural tradeoffs, and incident response.

• Experience managing engineering managers, building a leadership bench, not just IC teams.

• Expertise in modern cloud-native architecture: Azure/AWS, Kubernetes, microservices, event-driven systems, CI/CD.

• Demonstrated ability to improve delivery velocity and engineering quality simultaneously, not one at the expense of the other.

• Strong communication skills: comfortable presenting to executives and translating technical complexity into business terms.

Preferred

• Experience in logistics, supply chain, freight technology, or a similarly operationally complex, high-transaction-volume domain.

• Background building platforms that integrate with external systems, carrier APIs, ERP/WMS, EDI, load boards, or similar.

• Experience at a PE-backed or high-growth technology company scaling through a major engineering inflection point.
• Familiarity with data engineering and ML infrastructure, particularly integrating AI/ML capabilities into production software systems.
• Track record of building engineering cultures that retain top talent and consistently attract strong candidates.
• B.S. or M.S. in Computer Science, Software Engineering, or a related technical discipline.

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 remote 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:

$220,000 - $260,000

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.