Head, Technology Research & Development at Robertson & Company Ltd. — NeverHard
Head, Technology Research & Development at Robertson & Company Ltd. in Toronto, Ontario. Skills: AI, Architecture, Cloud Foundry, Ecommerce, Engineering Management. Apply on NeverHard.
Company
Robertson & Company Ltd.
Location
Toronto, Ontario
Type
full_time
Required skills:
AI
Architecture
Cloud Foundry
Ecommerce
Engineering Management
Java
Leadership
A growing B2B DTC Software Solutions Provider is at a pivotal moment and is in search of a Head of R&D to lead an AI-DLC Transformation & eCommerce Platform Modernization. Part of this modernization transformation exercise will include an internal cultural transformation and mindset shift as it pertains to the AI-DLC strategy.
Currently, they are investing strategically in technology to fuel growth, improve customer experience, and optimize operations. This requires modernizing their platform that is currently built on legacy code consisting of ColdFusion & Java. You will also need to evaluate the existing combination of tech stack and build a modernization strategy, which could potentially include rebuilding the engineering infrastructure. They need a Head of R&D to lead that transformation.
You’ll lead a lean, focused team of 8 internal engineers, 4 offshore engineers and 2 external partners. You’ll own the engineering vision and strategy, report directly to the President, and have real influence over how the business operates. This is a hands‑on leadership role—you’ll make architecture decisions, validate technical direction, and build a team that ships predictably.
You’ll manage technical debt strategically, knowing when to maintain what exists and when to rebuild. Beyond strategy, you stay involved in technical decisions. This isn’t a role where you delegate and disappear.
Your Core Priorities
Modernize the Engineering Infrastructure
Ensure the appropriate configuration of CI/CD pipelines, observability, and automation to support reliable, predictable weekly releases.
Integrate AI into the Development Process
Embed AI tools into how the team develops—automated testing, smarter code review, and faster iteration cycles. Make AI-assisted development a standard practice.
Document and Reduce Tribal Knowledge
Get institutional knowledge out of people's heads and into systems. Make the platform easier to maintain, easier to improve, and easier for new engineers to ramp into.
Ensure Security, Compliance, and Customer Trust
The platform serves end consumers. You’ll ensure it’s secure, compliant, and trustworthy—both technically and operationally.
Build a High‑Performing Engineering Team
Lead 8 internal engineers, 4 offshore engineers and 2 external partners. Set clear expectations, foster collaboration, and build a team that ships consistently and owns their work.
Success Metrics (First 6 Months)
CI/CD and observability infrastructure deployed and operational
Team shipping on a weekly cadence, predictably
AI tooling integrated and adopted by the engineering team
Platform documentation and runbooks in place
Tribal knowledge actively reduced; team cross‑trained
Technical roadmap locked, communicated, and on track
What We’re Looking For
Deep Engineering Leadership Experience
5+ years building and shipping software.
5 years leading technical teams. You’ve worked in and navigated the challenges of modernizing legacy systems—not theoretically, but hands‑on. You know what works and what doesn’t.
Experience with eCommerce platform modernizations
Experience migrating off of legacy platforms (ColdFusion and/or Java)
Technical Depth + Business Fluency
Technical excellence is essential. You also connect engineering decisions to business outcomes and speak the language of growth, margins, and customer impact. You can have credible conversations with the CEO and President about what your work means for the business.
Infrastructure & DevOps Track Record
You’ve successfully built or deployed CI/CD pipelines, observability systems, and automation. You’ve done this in resource‑constrained environments where you had to prioritize ruthlessly and move fast.
You’re grounded and operate well in uncertainty. You make decisions and move forward without recklessness. You communicate with clarity—especially when things are uncertain. Your team trusts you.
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