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The Descartes

Descartes is one of the most broadly deployed logistics and supply chain technology companies in the world. More than 26,000 customers around the globe use our cloud-based solutions to transform the way they move inventory and information. With record financial performance for more than 16 years, we lead the industry in innovation investment. Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world.

Director, Software Development

Location

Canada

Posted

60 days ago

Salary

C$140K - C$160K / year

Seniority

Lead

Job Description

Director, Software Development

The Descartes

Role Description Reporting to the VP of R&D- eComm in this newly created opportunity, we are looking for someone who will build and evolve a high-performing R&D organization that delivers Descartes/Sellercloud’s Inventory and Order Management Systems (IMS/OMS) with consistent, high-confidence roadmap execution and strong technical health. As Director, you will operate at the portfolio level, strengthening leadership leverage, delivery systems, investment clarity, and long-term scalability. Expected Outcomes - Leadership Scaling: Strengthen and evolve a manager-of-managers R&D organization, coaching R&D Managers and Tech Leads to independently own delivery, trade-offs, and people development. - Predictability & Flow: Deliver measurable improvements in roadmap predictability and flow, establishing consistent operating cadences that surface risks early and provide credible multi-quarter forecasting. - Healthy Technical Investment: Ensure engineering capacity is intentionally allocated across feature growth, architectural runway, and reliability improvements, with transparent trade-offs aligned in partnership with Product Management. - Operational Excellence: Improve key reliability indicators (e.g., incident recurrence, MTTR, change failure rate) by reinforcing shared engineering standards and embedding disciplined post-incident learning that drives systemic improvement. - Organizational Scalability: Define and communicate a forward-looking hiring and capability roadmap (4–6 quarters) aligned to business growth, with team structures designed to minimize bottlenecks and maximize clear ownership. Qualifications - 10+ years in software development with significant experience leading multiple teams through managers in a SaaS environment. - Proven success improving delivery predictability, engineering flow, and operational reliability through scalable systems; not individual heroics. - You design operating mechanisms, investment models, and feedback loops that connect engineering execution to business outcomes. - Experience evolving engineering operating models in growing organizations, building alignment across Product and technical leadership without becoming a bottleneck. - Demonstrated ability to coach and grow managers, build psychologically safe teams, and create durable leadership depth. - You translate complex technical trade-offs into clear business implications and foster transparency across teams. Benefits - Direct influence on how a strategic SaaS platform scales. - High visibility and partnership across Product, Operations, and Executive leadership. - Opportunity to shape the long-term engineering operating model. - Competitive compensation and flexible remote options. - A culture driven by impact that values ownership, clarity, and sustainable performance. - Salary Range: $140,000 - $160,000 CAD annually plus bonus. Company Description Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what’s most important to them. At Descartes, we don't just want a "culture fit"—we want someone who adds to our collective strength: - Transparency – Open, honest communication that builds trust. - Excellence & Expertise – High standards and continuous mastery of your craft. - Accountability – Ownership of commitments and outcomes. - Metric-Driven Results – Data-informed decisions focused on measurable impact.

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