Remote AI Transformation Lead

Commonsku Inc.; Toronto; Hybrid; CAD 130,000 - 160,000; Full time

Benefits offered by this job

Remote-first culture

HQ and in-person experiences

Health and dental benefits

RRSP/TFSA contributions up to $3,000 a

Twice-yearly company wide summits

A delightful team of smart people

Job summary

commonsku is a remote-first, community-driven team reshaping the promotional products industry. As AI Transformation Lead, you’ll help drive our internal AI transformation by designing and deploying AI workflows across teams, creating better outcomes for colleagues and customers, and collaborating with every department.

You’ll join a high-trust culture that values initiative, bold thinking, and practical value over hype.

Qualifications

• Proven track record of taking AI or automation initiatives from concept to production with measurable business impact
• Demonstrated experience redesigning workflows or business processes to materially improve how teams operate
• Practical fluency building with AI tools and understanding of how they integrate into business systems
• Experience partnering with cross-functional leaders to translate strategic priorities into actionable roadmaps and navigate change management
• Comfort operating with ambiguity, with a focus on iterative execution and clear communication
• Ability to work independently and asynchronously while prioritizing collaboration
• Experience (or excitement for) working with AI
• Bonus: Experience leading internal communities of practice, change champions, or multi-department enablement programs

Responsibilities

• Map high-value opportunities for AI across the company by understanding core team outputs, prioritizing impactful work to drive business and revenue outcomes
• Build and maintain a prioritized roadmap of internal AI-enabled transformations in alignment with team leads and cross-functional AI Champions
• Partner with teams to rethink work and workflow design from the outcome backward, determining the ideal balance of AI capabilities, human judgment, and connection
• Design and build AI-powered workflows and automations using agentic and AI-native tools alongside traditional automation platforms
• Turn successful pilot initiatives and experiments into durable, company-wide tools and practices
• Create tailored enablement assets—including workshops, job aids, and coaching to support team learning and adoption across structured and on-the-job environments
• Manage tracking and reporting for AI automation, efficiency gains, and tooling ROI
• Set and maintain internal best practices for AI usage, data integrity, and privacy

Skills

AI transformation

Automation

Workflow redesign

Cross-functional collaboration

Ambiguity management

Independent work

AI tools

Change champions

Job description

commonsku is a remote-first, community-driven team reshaping the promotional products industry. As AI Transformation Lead, you’ll help drive our internal AI transformation by designing and deploying AI workflows across teams, creating better outcomes for colleagues and customers, and collaborating with every department.

You’ll join a high-trust culture that values initiative, bold thinking, and practical value over hype.