Sr. Director, Software Engineering

We're looking for a strategic, results-oriented Senior Director of Software Engineering to lead the maturation and growth of our engineering organization. This is a pivotal role for an experienced leader who thrives in dynamic SaaS environments and is passionate about building scalable systems, cultivating engineering talent, and driving excellence across the development lifecycle.

As the Senior Director, reporting to our CTO, you will be responsible for improving software delivery through disciplined engineering practices, enhancing system reliability, and increasing team velocity and predictability. Your leadership will ensure we ship high-quality, high-performing, and resilient products - consistently and efficiently.

Key Responsibilities

Drive Engineering Excellence: Elevate development standards across architecture, code quality, test automation, performance tuning, and operational reliability. Embed quality and performance considerations throughout the development lifecycle.

Improve Engineering Efficiency: Optimize team workflows, processes, and tools to reduce cycle times, eliminate waste, and improve sprint predictability and throughput.

Lead Cross-Functional Collaboration: Partner closely with Product, Cloud and Quality to align technical initiatives with business priorities and drive shared accountability for outcomes.

Scale and Develop Teams: Attract, mentor, and grow high-performing engineering leaders and teams. Promote a strong feedback culture and career development at every level.

Data-Driven Leadership: Define and track engineering KPIs (e.g., key DORA metrics, predictability trends, defect rates, tech debt ratios) to guide continuous improvement and transparency.

Drive Process Maturity: Lead the evolution of Agile practices to improve sprint planning, forecasting accuracy, and delivery cadence. Foster consistency in estimation, retrospectives, and execution across teams.

Ensure Operational Excellence: Own engineering outcomes for availability, scalability, and maintainability of critical systems. Champion a culture of accountability and reliability.

Contribute to Technical Direction: Stay engaged with architectural decisions and system design reviews to ensure technical soundness and long-term sustainability.

Support Global Collaboration: Manage distributed teams across North America and utilize offshore partners where needed, fostering alignment, cohesion, and shared standards.

Qualifications

• Bachelor's degree in Computer Science or a related field.
• 7+ years of engineering leadership experience, including oversight of multiple teams and managers.
• Proven track record in scaling software engineering organizations in a SaaS (preferably B2B or enterprise) environment.
• Deep understanding of modern software engineering practices, Agile methodologies, and DevOps principles.
• Hands-on technical background with the ability to guide architectural and infrastructure decisions.
• Demonstrated success improving delivery speed, quality, and operational resilience at scale.
• Strong leadership, coaching, and stakeholder management capabilities.
• Experience leading distributed teams across time zones, including outsourced partners.
• Familiarity with cloud-native platforms and services (e.g., AWS, Azure).
• Understanding of compliance frameworks (SOC 2, GDPR, etc.) as they relate to software delivery and operations.

Benefits

• Paid Parental Leave
• Flexible PTO
• Certification(s) reimbursement
• Summer Fridays
• Extended Medical, Dental, Paid Sick Days, Vision, Life Insurance, and Disability Leave Coverage
• RRSP & Employer match

Equal Employment Opportunity: CARET is an Equal Opportunity, Affirmative Action Employer. The compensation information below is provided in compliance with job posting disclosure requirements.

Pay range: $210,000 - $215,000. Actual base pay will depend on varying circumstances, including the position, location, individual qualifications, market finances, and other operations business needs. Depending on the position, compensation may also include commission, bonuses, etc. Potential for bonuses is based on company performance and potential for merit increases is based on performance.

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