Head of Technology, Transformation Full-Stack Builder

Workleap is a Montreal-based tech company on a mission to make work simpler. As a Head of Technology, your mission will be to advance the organization's execution capacity by influencing, aligning, and evolving key teams. The role requires someone capable of making an impact in a matrix structure, leading through technical credibility and influence, and concretely contributing to the engineering vision.

Requirements

• Significant experience (at least 3–5 years) in an engineering leadership role within a growing or large-scale SaaS technology environment;
• Demonstrated ability to influence without relying solely on hierarchical authority, particularly in matrix structures;
• Strong technical credibility and willingness to be hands-on: ability to go deep, understand code, and contribute concretely;
• Experience managing leaders, including contexts where 3 directors may report to the position;
• Relevant experience managing or coordinating organizations of approximately 20 people;
• Ability to lead organizational transformation mandates with high expectations for impact;
• Experience improving execution velocity while maintaining a high level of quality;
• Good judgment to navigate trade-offs between security, quality, innovation, and speed;
• Strong interest in new ways of developing software in an AI-influenced context;
• Ability to quickly establish credibility with very senior profiles and to challenge strong opinions constructively;
• Experience in a Microsoft /.NET environment is an asset; otherwise, a strong interest in quickly learning this ecosystem is important;

Benefits

• Generous Paid Time Off
• 401k Matching
• Retirement Plan
• Visa Sponsorship
• Four Day Work Week
• Generous Parental Leave
• Tuition Reimbursement
• Relocation Assistance