Job Description

About Us

At

Shift Fleet AI

, we're transforming fleet management through cutting-edge, AI-powered technology. Our platform empowers businesses to optimize operations, cut costs, and gain total visibility into their logistics. We're growing fast--and we're just getting started. If you're excited about working in a fast-paced, high-impact environment where innovation and growth are constant, you've come to the right place.

Why This Role Matters

We are seeking a

Head of Engineering & Product

to lead our technology team while being hands-on in building our core platform. This role requires a rare blend of technical expertise, leadership ability, and product thinking. You'll manage developers, own delivery timelines, and also contribute directly to coding and system design. You'll work closely with founders and stakeholders to translate vision into scalable, customer-ready products.

What You'll Do

Leadership & Management

Lead and mentor the engineering team; establish clear goals, processes, and accountability. Oversee sprint planning, code reviews, and technical architecture decisions. Build a high-performance culture focused on delivery and innovation. Hands-On Development Contribute directly to the codebase (backend, frontend, and full stack) Ensure high-quality, maintainable, and scalable code. Troubleshoot and resolve complex technical challenges.
Product & Strategy

Partner with leadership to define the product roadmap and prioritize features. Translate business needs into technical requirements and clear deliverables. Balance speed, quality, and technical debt while shipping new features.
Operations & Growth

Own development timelines and ensure successful product releases. Support recruitment, onboarding, and scaling of the engineering team. Implement best practices for DevOps, security, and infrastructure management.

What You Bring

Bachelor's degree in Computer Science or equivalent experience.

5+ years of experience in software development, with at least 2 years in a leadership or management role.

Proven experience leading engineering teams in an Agile development environment (familiarity with JIRA is a plus), while still coding. Strong skills in modern tech stacks: Python, Node.js, Nest.js, React, MongoDB. Understanding of product development lifecycle and user-centric design. Excellent communication and leadership skills. Entrepreneurial mindset; comfortable in a fast-moving startup environment.
Nice to Have

Experience with AI/ML, cloud platforms (AWS, GCP, Azure), or SaaS product development. Prior experience in a startup or building products from zero to scale.

What We Offer

Compensation: Base salary of $70,000-CA?$80,000 Career development opportunities Influence over technical decisions and product direction. A collaborative culture that values speed, ownership, and innovation. Small team, big impact, and real support from leadership..

Ready to Build Something Big?

Join Shift AI and help shape the future of fleet management. If you're ambitious, proactive, and ready to grow with a company that values results and innovation, we'd love to hear from you.

Job Type: Full-time

Pay: $70,000.00-$80,000.00 per year

Benefits:

On-site parking Paid time off
Ability to commute/relocate:

Toronto, ON M1S 5K7: reliably commute or plan to relocate before starting work (required)
Experience:

Leadership: 2 years (required) Software development: 5 years (required) Startup environment: 1 year (required)
Work Location: In person