Director, Software Engineering & Innovation

About the Role

This leadership position at Sherweb involves overseeing a large software engineering team of around 80 professionals through five managers, driving delivery, execution, and engineering excellence. The role focuses on evolving the software development lifecycle (SDLC) in an AI-enabled context and fostering leadership growth.

Key Responsibilities

• Lead and expand a multi-team software engineering organization delivering high-quality and secure software products and platforms.
• Create a culture of continual value delivery improvement among managers and teams.
• Promote and develop advanced engineering methodologies such as Team Topologies, DevOps, platform thinking, AI-assisted development, and Spec-Driven Development.
• Coach five managers to increase autonomy, accountability, and leadership capabilities to grow their teams.
• Innovate the SDLC by integrating AI-enabled processes, guardrails, experimentation, metrics, and adoption frameworks to enhance quality and developer experience.
• Serve as a trusted collaborator with cross-functional leadership—product, architecture, operations, security, finance, and executives—to align technical execution with business goals.
• Infuse energy, clarity, and enjoyment into the organization while maintaining professionalism and focus.

Daily Activities

• Develop and communicate an operational plan linking objectives, delivery priorities, engineering health, and corporate strategy.
• Lead, mentor, and hold accountable managers who oversee development teams and platform capabilities.
• Balance product priorities, customer outcomes, architecture, reliability, security, and capacity across projects.
• Implement new SDLC practices including AI-assisted coding, Spec-Driven Development, quality gates, automated validations, and continuous improvements.
• Collaborate with architecture leads to guide technical decisions, manage complexity, and optimize team interactions.
• Work closely with product leadership to understand customer problems, product strategy, trade-offs, and economics of delivery.
• Enhance management practices including recruitment, performance, coaching, succession planning, compensation, and engagement.
• Identify and develop high-potential talent ensuring motivation, visibility, and growth opportunities.
• Address challenging conversations and decisions with respect and decisiveness, coaching managers accordingly.
• Contribute to governance, compliance (SOC 2, PCI-DSS, ISO 27001), audits, tax credit support, and internal controls.
• Champion Sherweb’s values fostering an inclusive, accountable, and high-performing work culture.

Required Experience and Skills

• Proven leadership of sizable software engineering groups (50+ people) with multiple direct manager reports.
• Experience coaching managers, enhancing leadership abilities, and succession planning.
• Background delivering intricate modern SaaS, API-centric, cloud-based, or large-scale web applications.
• Expertise in modernizing engineering practices: CI/CD, automated testing, code reviews, source control, observability, DevOps, security, reliability, and deployments.
• Practical use of AI in SDLC such as AI-assisted code generation, reviews, test automation, and documentation.
• Knowledge of Spec-Driven Development or spec-first workflows leveraging structured requirements and validation.
• Understanding of organizational design including Team Topologies, cognitive load, value streams, and team interaction patterns.
• Strong judgment, courage to lead difficult conversations, conflict resolution, and decision-making skills.
• Ability to align with product leadership on discovery, roadmaps, customer value, and delivery economics.
• Effective communication to influence both technical and executive stakeholders in English and French (spoken and written) or capability to operate bilingually.

Desirable Experience

• Partnering closely with product management in a SaaS or platform environment.
• Leading platform engineering, developer experience, internal tooling, or architecture teams.
• Scaling AI adoption using governance, enablement, secure tools, and measurable objectives.
• Implementing organizational changes aligned with Team Topologies, Domain-Driven Design, or value-stream approaches.
• Influencing or leading architecture teams and senior technical leadership.

Benefits and Work Environment

• Dynamic and supportive culture emphasizing passion, teamwork, and integrity.
• Flexible, fast-paced workplace adapting to employee needs.
• Diverse, inclusive, and equitable work culture with state-of-the-art technology and tools.
• Annual performance-based salary reviews and recognition for innovative thinking.
• Competitive total compensation including a yearly base salary between $145,000 and $180,000 CAD.
• Vacation time respecting prior experience and additional paid time off for rest.
• Customizable benefits plans and flexible savings options.
• Monthly allowance for home internet expenses.
• Significant opportunities for career development and ongoing training.
• A rich calendar of community-building activities both virtually and in-person.

Additional Information

Fluency in English is essential due to Sherweb's international customer base and communication requirements. The position demands frequent written and oral interaction with English-speaking clients. Sherweb commits to pay transparency and tailors salary packages to candidates' unique qualifications to ensure fair and competitive compensation.