Head of Engineering

ZipRecruiter; Greater Toronto Area; On-site; CAD 120,000 - 180,000; Full time

Job summary

A leading company in trade technology is seeking a Head of Engineering to lead their engineering function and contribute to product development. The ideal candidate will have experience in fast-paced environments, a passion for coding, and a strong leadership presence. Join a mission-driven team to shape the future of logistics and AI.

Benefits

Real ownership

Fast feedback loops

Sharp, mission-driven team

Equity opportunities

Qualifications

• Experience leading engineering at a fast-moving startup.
• Comfortable with both IC work and organizational leadership.
• Experience building production software in logistics, fintech, or AI.

Responsibilities

• Lead engineering function across quoting, AI agents, and operational automation.
• Contribute directly to the codebase and solve production problems.
• Set technical direction and drive architectural decisions.

Skills

Leadership

Coding

Problem Solving

Collaboration

Technical Direction

Job description

Job Description

About Starboard

Starboard is building the AI operating system for global trade. Our platform helps freight forwarders quote faster, price smarter, and automate operations—replacing spreadsheets and email threads with intelligent, real-time workflows.

We’re backed by Eclipse Ventures and already power pricing desks at some of the most forward-thinking logistics companies globally. The product is in-market, the demand is real, and now we’re scaling both usage and the team behind it.

The Role

We’re looking for a Head of Engineering who thrives in a build-and-lead environment. You’ll be the technical leader of the company—setting the architectural direction, mentoring engineers, and scaling our systems. But you’ll also be expected to stay close to the code. That means owning tickets, solving production problems, and helping ship product alongside the team.

This role is perfect for someone who wants to lead by example—both as a builder and a team shaper.

What You’ll Do

• Lead Starboard’s engineering function across quoting, AI agents, TMS integrations, and operational automation
• Contribute directly to the codebase—solving tickets, reviewing PRs, and unblocking engineers in the critical path
• Set technical direction and drive architectural decisions that ensure scalability, maintainability, and speed
• Hire and grow a sharp, scrappy team of engineers who ship fast and own outcomes
• Collaborate closely with product and design to scope and deliver features that win adoption
• Establish best practices around code quality, deployment, and observability—without slowing velocity
• Help shape a culture that values ownership, curiosity, and action

You Might Be a Fit If…

• You’ve led engineering at a fast-moving startup and enjoy coding just as much as building teams
• You’re comfortable switching between IC work and org leadership—especially in early-stage chaos
• You’ve built production software in high-stakes domains (logistics, fintech, AI, ops tools)
• You like solving real-world user problems and turning messy workflows into clean, working systems
• You believe in clear code, fast feedback loops, and ruthless prioritization
• Bonus: You’ve worked on logistics tech, AI/ML systems, or complex data pipelines

Why Join Starboard

• Real ownership: You’ll define and build the technical foundation of a high-growth, high-impact product
• Fast feedback loops: We ship every week and obsess over user feedback
• Sharp, mission-driven team: We move fast, care deeply, and punch above our weight
• Upside that matters: Join early, take equity, and help define the future of trade tech