Director Of Engineering - Remote Eligible

Director of Engineering

The Director of Engineering is the senior technical leader responsible for managing the engineering team, ensuring strong execution on the product roadmap, and guiding technical decisions in close partnership with the Chief Product Officer. This role is a player-coach: someone who can architect, prototype, and occasionally code, while primarily focusing on enabling the engineering team to deliver high-quality, scalable, and AI-enabled solutions. This leader brings a future-oriented mindset — embracing AI-native development practices, rapid prototyping, and iterative delivery — while also providing stability and stewardship for our existing .NET-based systems.

Responsibilities

• Team Leadership – Manage and mentor engineers, building a culture of accountability, collaboration, and continuous learning.
• Technical Direction – Provide architectural guidance, particularly around modernizing legacy systems and adopting AI-native practices.
• Execution – Ensure engineering delivers against the product roadmap with speed, quality, and reliability.
• AI-Enabled Engineering – Champion the use of AI tools, workflows, and automation to scale engineering output from 1x to 10x.
• Hands-On Contribution – Prototype new ideas, fix critical bugs, and dive into code when needed to unblock the team.
• Cross-Functional Collaboration – Partner closely with Product to align engineering work with customer and business needs.
• Operational Excellence – Ensure engineering processes, documentation, and systems support both velocity and stability.

Requirements

• Proven experience leading software engineering teams (player-coach, not just people-manager).
• Strong architectural judgment and ability to work with multiple tech stacks (experience with .NET a plus, but not required).
• Familiarity with modern languages/frameworks (e.g., Python, TypeScript, Go) and cloud infrastructure (AWS and Kubernetes preferred).
• Demonstrated use of AI in development workflows (RAG, LLMs, copilots, automation).
• MVP-first mindset: thrives in prototyping and rapid iteration environments.
• Comfortable reporting into a Chief Product Officer and working as a strategic partner rather than a C-level executive.

How This Role Fits

• Reports to: Chief Product Officer (CPO)
• Direct reports: Engineering team (individual contributors, possibly team leads as we grow)
• Partnership: Act as the technical counterpart to the CPO, who drives product strategy and vision.
• Goal: Build a high-performing engineering team that delivers on roadmap, modernizes our systems, and embraces AI-native development.

Compensation

We offer a starting base salary of $195,000.00 — $250,000.00 CAD depending on experience. We take a holistic approach to compensation at Stamped. Total compensation includes salary, benefits, RRSP, ESPP, an annual education allowance and other perks.

Benefits

• Work with a passionate, multinational and multi-talented group of tech enthusiasts who always go that extra mile
• Work directly with company leadership
• A fully remote company driven by deliverables, not hours
• Comprehensive benefits package (health, dental, HSA, EFAP and more)
• Unlimited PTO
• Grow and own your area
• $650 home office set up allowance
• $650 annual education budget
• Employee Share Purchase Plan
• RRSP Matching with up to 4% employer matching
• Paid Parental leave (up to 12 weeks)

Why Choose Stamped?

At Stamped, we believe that innovative ideas can come from anywhere and everywhere. As a company, we fully embrace a growth mindset through active listening, agile problem-solving, and empathetic decision-making every single day. We are part of the Tiny family, we've experienced significant growth, and our customers love us. If you're the type of person who seeks out new challenges, wants to work with some of the best people in the SaaS ecommerce space, and wants to make a meaningful impact on a growing company, this is for you! At Stamped, we are committed to building a diverse and inclusive space where people are free to be their whole and authentic selves. If you are excited about this role but your previous experience does not align with every qualification, we encourage you to apply anyways. You might be a fit for this or one of our other opportunities.