Director, Software Development

Descartes Unites the People and Technology that Move the World

The need for efficient, secure, and agile supply chains and logistics operations has become ever more critical and complex. By combining innovative technology, powerful trade intelligence and the reach of our network, Descartes helps get goods, information, transportation assets, and people where they’re needed, when they’re needed.

We’re 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, enhancing productivity, better serving customers, thriving competitively, keeping pace with evolving regulations, and responding to rapidly changing market conditions. 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. Learn more at www.descartes.com.

We’re growing fast and invite you to join our amazing team.

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.

What You Bring

• Portfolio Leadership Experience: 10+ years in software development with significant experience leading multiple teams through managers in a SaaS environment.
• Operational Impact: Proven success improving delivery predictability, engineering flow, and operational reliability through scalable systems; not individual heroics.
• Systems‑Level Thinking: Design operating mechanisms, investment models, and feedback loops that connect engineering execution to business outcomes.
• Change & Influence: Experience evolving engineering operating models in growing organizations, building alignment across Product and technical leadership without becoming a bottleneck.
• Leadership Leverage: Demonstrated ability to coach and grow managers, build psychologically safe teams, and create durable leadership depth.
• Executive Communication: Translate complex technical trade‑offs into clear business implications and foster transparency across teams.

Culture Add (Our TEAM Values)

• 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.

What We Offer

• 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, and a culture driven by impact.
• A culture that values ownership, clarity, and sustainable performance.

Salary Range: $130,000 – $140,000 CAD annually plus bonus. Compensation information provided is a good faith estimate for this position only. Factors that may be used to determine your actual salary may include your specific skills as well as the years of experience you have. Similar positions located in different geographic regions may not receive the same compensation.

Join Us

As we scale, we’re looking for new doers, collaborators and innovators to join Descartes in uniting the people and technology that move the world as the Global Leader in Logistics and Supply Chain Technology. We’re entrepreneurial, hardworking, geeky‑in‑a‑good way problem solvers. Guided by our values, we nurture a TEAM focused culture that invests in people and creates opportunities for advancement across a broad spectrum of career paths. We prioritize work‑life balance and foster an environment with the space to take ownership, to be heard, and to carve a path for your individual accomplishments to help drive our success. At Descartes, everyone has a voice and the best idea wins, regardless of who makes it. We offer competitive compensation, great benefits, remote and flexible work hours, and the opportunity to join a company on an awesome mission with a great existing team and trajectory.

Descartes also has a deep sense of environmental responsibility. Learn more about how we helped our customers save over 552,000 metric tons of CO2 in 2020 by reducing fuel and paper consumption: https://www.descartes.com/who-we-are/social-responsibility-sustainability/environmental-impact. Join a team that’s committed to working with customers to conserve resources and enhance sustainability.

If you feel you have 70% of the qualifications we are looking for, and Descartes sounds like the team and the mission you want to be part of, apply now. We can’t promise it will be a fit, but we do promise to consider your experience.

We conduct a mix of in‑person and virtual interviews. Virtual interviews are held via Microsoft Teams and are recorded and transcribed. We may utilize AI tools to support our hiring team in notetaking, summarization, and internal training. AI tools are not used in our recruitment process for decision‑making purposes. Recordings, transcripts, and notes are used for recruitment, including improvement of our process, and record‑keeping purposes. Should you have any questions or concerns about our process, please connect with our hiring team in advance of scheduled interviews.

We are an Equal Employment employer. We do not discriminate in hiring on the basis of sex, gender identity, sexual orientation, race, color, religious creed, national origin, physical or mental disability, protected status, or any other characteristic protected by federal, provincial, or local law. For more information about our commitment to equal employment opportunity, please review our Code of Business Conduct and Ethics at Descartes.com. Descartes is committed to working with and providing reasonable accommodations to job applicants with disabilities. Applicants in North America with a disability who require a reasonable accommodation for any part of the application or hiring process can email us at hrna@descartes.com. Provide your name and contact information along with the accommodation needed to assist you with the application process. Your request will be responded to as soon as possible. Reasonable accommodations will be determined on a case‑by‑case basis.