Position Summary

ICS is an established B2B retail software provider at a pivotal moment. The company is investing strategically in technology to fuel growth, improve customer experience, and optimize operations — and that investment requires modernizing a mature, business-critical platform. We are looking for a transformational Chief Technology Officer to own that mandate.

Job Description

Chief Technology Officer

Position Summary

ICS is an established B2B retail software provider at a pivotal moment. The company is investing strategically in technology to fuel growth, improve customer experience, and optimize operations — and that investment requires modernizing a mature, business-critical platform. We are looking for a transformational Chief Technology Officer to own that mandate.

Reporting directly to the President, the CTO will own the engineering vision and strategy, shape the target architecture and modernization path, and lead the continued cultural transformation to AI-driven development (AI-DLC) across the organization. This is a hands‑on, player‑coach executive role: the CTO sets direction and leads through managers and team leads while remaining close enough to architecture, cloud, security, product, and delivery decisions to challenge assumptions and intervene when required. The primary mandate is to modernize the legacy platform and the engineering organization around it, while protecting business continuity, customer confidence, and future scalability.

The ideal candidate is a balanced transformation leader who combines executive judgment, product orientation, technical credibility, and disciplined execution — someone who raises standards and makes difficult trade‑offs while building trust, developing leaders,



and guiding the organization through change with clarity, even under uncertainty.

Key Responsibilities

- Own technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery across the organization.
- Set product direction and roadmap prioritization, aligning technology investment with commercial priorities.
- Lead platform and eCommerce modernization, including migration off the legacy platform, by evaluating rewrite, re‑platform, refactor, and phased‑modernization options and recommending a target architecture and delivery path.
- Establish CI/CD pipelines, observability, and automation to support reliable, predictable weekly releases, and set the cloud and hosting modernization roadmap, including sequencing, migration controls, and rollback readiness.
- Embed AI tooling into the development process (AI‑DLC) — automated testing, smarter code review, faster iteration cycles — and make AI‑assisted development standard practice across engineering.
- Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance for a platform serving both trade customers and end consumers.
- Reduce tribal knowledge by getting institutional knowledge out of people’s heads and into documentation and runbooks, making the platform easier to maintain, improve, and ramp new engineers into.
- Lead, develop,



and retain a distributed 14-person engineering organization spanning internal, offshore, and external partner resources, setting clear expectations and building a team that ships consistently and owns its work.
- Evaluate and prioritize commercially viable customer‑facing AI capabilities on their commercial merit, separate from internal AI‑DLC tooling adoption.
- Maintain selective involvement in strategic customers, major escalations, product advisory discussions, and technically complex opportunities.
- Provide periodic Board and executive exposure on modernization, technology investment, strategy, cybersecurity, and risk.

AI and Operating Expectations

ICS is actively investing in AI across operations, product development, and go‑to‑market execution. The CTO is expected to make AI‑driven development the organization’s standard operating model, not an experiment.

- Make AI‑assisted development a standard practice across the engineering organization, embedding AI tooling into automated testing, code review, and iteration cycles.
- Establish the organization’s AI‑DLC maturity baseline and a validated target and timeline, and lead the mindset shift required to get there.
- Separately assess and prioritize customer‑facing AI opportunities on commercial merit, distinct from internal AI‑DLC tooling adoption.
- Model disciplined AI-enabled decision‑making for the engineering organization, verifying outputs and exercising sound judgment with technical and customer data.
- Champion current workflows and process improvements that support ICs’s broader AI‑enabled operating model and raise team effectiveness.

Required Qualifications

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📌 Chief Technology Officer (Canada)
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📍 Canada