Director, Software Engineering & Innovation
$31,200–$31,200 year
HybridMontréal, Quebec, Canada or Quebec, Canada
Job Summary
Set and communicate a clear operating plan connecting department objectives, delivery priorities, and Sherweb's business strategy. Lead, coach, and hold accountable a team of managers overseeing software development, platform capabilities, and delivery practices. Drive execution across multiple initiatives by balancing customer outcomes, product priorities, architectural direction, operational reliability, security, and capacity constraints. Introduce and scale new ways of working across the SDLC, including AI-assisted development, Spec-Driven Development, agentic coding workflows, quality gates, automated validation, and continuous improvement practices. Partner with architecture leaders to ensure teams make sound technical decisions, manage complexity, and reduce cognitive load. Collaborate closely with product leadership to understand customer problems, product strategy, value streams, roadmap trade-offs, and delivery economics. Strengthen management practices across recruitment, performance management, coaching, talent development, succession planning, compensation reviews, and engagement. Identify high-potential employees and managers, create growth paths for them, and ensure key talent remains challenged, engaged, and visible. Have direct and respectful tough conversations when required, take difficult decisions when they are the right ones, and coach managers to do the same. Contribute to governance, audit, compliance, and operational practices, including SOC 2, PCI-DSS, ISO 27001, tax credits support, and internal controls. Represent Sherweb's values and help create an inclusive, open-minded, respectful, accountable, and high-performing culture.
Required Qualifications
- Significant experience leading software engineering organizations at scale, ideally 50+ people, with multiple managers reporting into the role
- Proven ability to coach managers, raise leadership maturity, build accountability, and develop succession capacity
- Strong experience delivering complex modern software products or platforms, ideally multi-tenant SaaS, API-centric, cloud-based, or high-scale web applications
- Demonstrated ability to modernize engineering practices across CI/CD, automated testing, code reviews, source control, observability, DevOps, security, reliability, and deployment practices
- Practical experience introducing AI into the SDLC, such as GitHub Copilot, agentic coding, AI-assisted reviews, automated test generation, AI-enabled documentation, or similar practices
- Familiarity with Spec-Driven Development, spec-first workflows, or equivalent approaches that use structured requirements, constraints, acceptance criteria, and validation as durable engineering artefacts
- Strong organizational design instincts; familiarity with Team Topologies, cognitive load, value streams, enabling teams, platform teams, stream-aligned teams, and interaction modes
- Excellent judgement, managerial courage, conflict resolution skills, and ability to make difficult decisions without drama
- Ability to partner with product leaders and understand product discovery, roadmap trade-offs, customer value, commercial impact, and delivery economics
- Strong communication skills with the ability to influence technical and non-technical stakeholders, including executive audiences
- Bilingual French and English, spoken and written, or strong ability to operate effectively in both languages
Desired Qualifications
- Has led or partnered closely with product management in a SaaS or platform organization
- Has led platform engineering, developer experience, internal tooling, architecture, or technical enablement functions
- Has scaled AI adoption across teams using governance, enablement, communities of practice, secure tooling, and measurable adoption goals
- Has led organizational changes based on Team Topologies, Domain-Driven Design, platform operating models, or value-stream alignment
- Has experience with architecture leadership and could eventually lead or strongly influence architects and senior technical leaders
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