Role Summary:

An established B2B and direct-to-consumer retail software provider is hiring a hands-on Chief Technology Officer. The company's mature point-of-sale and eCommerce platform, built on legacy Java and Swing, is central to how its customers run their businesses. Leadership is committed to modernizing it.

Reporting to the President, you'll own technology and product strategy, define the target architecture, and lead the move to AI-driven development across the engineering team. This is a player-coach role. You'll make architecture decisions, manage technical debt deliberately, and build a team that ships predictably. You'll also decide when to maintain what exists and when to rebuild it.

Role: Chief Technology Officer

Client: B2B and direct-to-consumer retail software provider

Location: Remote

Duration: Full Time Permanent

What You'll Own

- Technology strategy, architecture, infrastructure, DevOps, and software delivery
- Product direction and roadmap prioritization aligned with commercial goals
- Platform and eCommerce modernization, including migration off legacy Java and Swing, and the cloud roadmap
- CI/CD, observability, and automation to support reliable weekly releases
- Adoption of AI-assisted development (AI-DLC) as standard practice, plus disciplined evaluation of customer-facing AI opportunities
- Cybersecurity, IT general controls, compliance, business continuity, and disaster recovery
- Leadership of an approximately 14-person distributed engineering organization across internal, offshore, and partner resources
- Regular engagement with the executive team and Board on modernization, investment, and technology risk

What Success Looks Like

- First 60 days: A full technology, product, and delivery assessment is complete. Modernization options are evaluated and leadership is aligned on priorities.
- By 120 days:



The target architecture and a funded roadmap are approved. Release infrastructure is operating on a predictable weekly cadence. AI tooling is adopted across the team, and platform knowledge is documented and shared.
- By 12 months: Modernization progress is measurable, delivery is more predictable, the platform is more resilient, and there is a explicit path to greater AI-DLC maturity.

What You Bring

- Prior experience as a CTO, VP of Engineering, or in an equivalent executive technology role
- 15+ years in technology, including 10+ years leading software development teams
- Hands-on experience modernizing legacy systems, ideally a POS or eCommerce platform, or a migration off Java and Swing
- A track record of building CI/CD, observability, and automation in lean, resource-constrained environments
- Experience leading distributed teams that include internal, offshore, and external partner resources
- Executive oversight of cybersecurity, technology risk, and business continuity
- The business fluency to connect engineering decisions to growth, margin, and customer impact

Nice to Have

- Retail technology, point-of-sale, eCommerce, or payments experience
- Experience in specialty, grocery, or regulated retail
- AWS cloud modernization leadership (Azure or Google Cloud experience will be considered)
- Vertical SaaS, fintech, ERP, or other high-availability transaction environments

Interview Stages:

- Virtual meeting with President
- Technical Round Interview
- Ideal Start Date December

How You Lead You are a steady transformation leader. You make sound decisions with incomplete information and communicate clearly when things are uncertain. You raise standards and address problems directly. You build teams that trust you and take ownership of their work. You're credible in the boardroom and effective at the whiteboard.

📌 Chief Technology Officer (Toronto)
🏢 Robertson u0026 Company
📍 Toronto