Job Description

Toast is recruiting on behalf of a Calgary-based software company operating in the enterprise SaaS space. The company has a team of roughly a dozen engineers and is building an AI-native platform targeting the enterprise resource planning market. They are early in their growth stage and moving fast, with a clear product direction set at the executive level and an engineering team that owns how that product gets built. This is a rare opportunity to join a company that is genuinely committed to AI-native development, not as a talking point but as a core part of how the team ships software every day.

Responsibilities

Lead engineering as a true player-coach, staying actively in the codebase by opening pull requests, reviewing code, debugging production issues, and personally driving significant technical work forward.
Serve as the senior technical fallback when the team encounters hard problems, getting in the code alongside them rather than directing from a distance.
Set and hold the standard for engineering quality, code review, and technical decision-making across the team.
Use time in the code as an active coaching opportunity through pairing and code review as a teaching surface.
Use AI coding agents as a core part of your daily development workflow and teach the broader team how to work effectively with them, establishing patterns and raising throughput across the team.
Bring a clear perspective on how engineering practices shift when a significant portion of code is agent-generated, including changes to review processes, testing, and feature scoping.
Lead, coach, and develop a team of approximately eight engineers including architects and developers, owning outcomes and individual growth for each person.
Provide direct and candid performance feedback and hold the team accountable for delivery.
Partner directly with the CEO to translate product vision into a sequenced and realistic technical plan.
Work closely with Design and Delivery teams to align engineering execution to customer needs.
Partner with the VP of Operations on engineering department strategy, team structure, technical roadmap, and capability planning.

Requirements

8 or more years of professional full-stack software engineering experience, with at least 3 years leading engineering teams at a senior or director level.
Active, daily, hands-on use of AI coding agents such as Claude Code, Cursor, or Copilot Workspace in your own development work, with the ability to speak specifically to workflows, prompting patterns, and where agents succeed or fall short.
Demonstrated experience rolling out AI coding agents or AI-assisted development practices across a team, including the change management and review process changes that come with it.
Demonstrated ability to remain hands-on as a senior leader, with code, pull requests, or technical work personally shipped in the last 12 months.
Proficiency in two or more of TypeScript, Node.js, Java, or Go.
Strong working knowledge of modern cloud-native tooling including Docker and Kubernetes.
Strong understanding of relational databases and SQL.
Excellent communication skills with the ability to constructively challenge ideas in a fast-moving environment, including at the executive level.
Experience leading engineering in an early or mid-stage SaaS company is an asset.
Experience with SAP or other enterprise platforms is an asset.
Experience setting up evals, telemetry, or guardrails for agent-assisted development is an asset.

Benefits

Salary range of $180,000 to $220,000 CAD.
A genuine opportunity to shape the technical direction of a product at the intersection of enterprise software and AI, with real downstream impact on how large organizations run their core business operations.
Direct partnership with the CEO and meaningful influence over how the engineering team works.
Real resources and organizational commitment to pursue AI-native development, not just talk about it.
A front-row seat to lead engineering at a moment when AI is fundamentally changing how software gets built.

Director of Engineering