Director of Engineering in Winnipeg

Our client is a fast-growing B2B SaaS company modernizing the building-supply industry through technology. Their platform helps independent dealers and wholesalers manage the complete order-to-cash process, including branded digital storefronts, professional customer portals, accounts receivable automation, and secure online payments. The platform integrates deeply with complex legacy and modern ERP systems, helping building-supply businesses sell more efficiently, serve their customers better, and get paid faster.

With the company continuing to expand its platform and AI capabilities, this is an opportunity to join an organization at an important stage of growth and have a significant impact on its engineering organization.

The Opportunity: Our client is looking for an experienced Director of Engineering to take ownership of the day-to-day leadership and operational execution of a growing engineering organization. The CTO is increasingly focused on the company's broader AI strategy, AI product development, and architectural innovation. This role will become the operational leader for Engineering, ensuring the team can execute quickly while maintaining the stability, scalability, security, and reliability expected from a mission-critical SaaS platform.

What You'll Do:

• Lead, manage, coach, and develop a distributed engineering organization of 15+ engineers across frontend, backend, and infrastructure.
• Help scale the engineering organization to 20+ engineers.
• Establish clear expectations around ownership, accountability, technical quality, and delivery.
• Develop engineering leaders and create a strong culture of continuous improvement.
• Partner closely with Product, Design, and the CTO to prioritize and execute the engineering roadmap.

Accelerate Delivery Through AI:

• Champion the adoption of AI-assisted development tools throughout the software development lifecycle.
• Explore and implement technologies such as Claude, automated code review, AI-powered QA, monitoring agents, and other developer productivity tools.
• Identify opportunities to reduce engineering toil and increase development velocity without sacrificing quality.
• Help establish practical processes for using AI effectively within a modern engineering organization.

Build a Highly Reliable Platform:

• Establish and maintain strong CI/CD, automated testing, observability, and monitoring practices.
• Ensure engineering processes support high availability and minimize regressions.
• Help maintain the reliability and security of systems handling payments, accounts receivable workflows, and high-volume transactional data.
• Establish appropriate engineering standards and guardrails as the company scales.

Support Customer-Facing AI:

• Partner with the CTO and Product organization to scale and operationalize AI capabilities.
• Help bring AI-powered features into production reliably and at scale.
• Support technologies and workflows involving document parsing, OCR, NLP, and AI-assisted order entry.

Scale Complex Integrations:

• Provide technical leadership for integrations with ERP and other external systems.
• Help ensure integrations are scalable, secure, fault-tolerant, and capable of handling high volumes of data.
• Work with systems that may include both modern cloud APIs and complex legacy or on-premise infrastructure.
• Establish predictable delivery processes and clear engineering metrics.
• Drive effective sprint planning, OKRs, and prioritization.
• Remove organizational and technical blockers.
• Foster a culture of accountability, collaboration, learning, and psychological safety.
• Balance speed of execution with appropriate technical standards and long-term maintainability.

Frontend: React, TypeScript

What We’re Looking For:

• 7+ years of engineering leadership experience.
• 3+ years managing remote or distributed engineering teams.
• Experience leading engineering organizations in a high-growth B2B SaaS environment.
• Experience scaling engineering teams and establishing effective development processes.
• A strong understanding of software architecture and the ability to determine when to move quickly versus when stronger technical standards are required.
• A pragmatic, hands-on leadership style.
• Experience working cross-functionally with Product, Design, and Engineering.
• Strong interest in AI-assisted software development and a practical understanding of how AI can improve engineering productivity.

Nice to Have:

• Experience with fintech, payments, invoicing, accounts receivable, or financial systems.
• Experience building high-reliability applications where downtime or data integrity issues directly impact customers and revenue.
• Experience in construction technology, ConTech, PropTech, building materials, or supply-chain technology.
• Experience working with ERP platforms or other complex enterprise systems.
• Experience taking customer-facing AI products from development into production.

Why Join Our Client?

• Make an Impact in a Massive Industry: Play a key role in modernizing how building materials are ordered, sold, and paid for across North America.
• Real Traction: Join a company with an established customer base, significant transaction volume, and a strong opportunity for continued growth.
• Remote & Flexible: Work remotely with a distributed engineering organization and enjoy competitive compensation, equity, and comprehensive benefits.