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

Ready to help reshape a $26B industry and build the future of branded merch?

commonsku is revolutionizing the promotional products industry. Our platform empowers branded merch distributors to work smarter — managing projects, building quotes, placing orders, and collaborating with clients and suppliers seamlessly through the power of the Connected Workflow.

We’re a remote-first, community-driven team obsessed with elevating our customers, their clients, and the broader industry. Our values – Community First, Ten Steps Ahead, Fast Forward, and Delightful Work – guide us. We believe you can innovate, push forward, and do more, while also sharing a laugh, supporting your colleagues, and having a life outside of work. We’re also proud to be officially recognized as a Certified Great Place to Work® in Canada.

If you’re energized by ambitious work, creative collaboration, and helping to build something great, you’ll want to keep reading.

About the Role: AI Transformation Lead

We’re growing — and we’re hiring an AI Transformation Lead to join our team! In this role, you’ll help us lead commonsku’s internal AI transformation as an embedded internal consultant and builder, identifying, designing, and deploying AI workflows across teams to create better outcomes for our colleagues and customers. You’ll collaborate closely with teammates across all departments, contribute to a high-trust environment, and play a direct role in shaping the future of the industry

About You

You’re not just looking for a job — you’re looking for a place to do your best work. You bring:

• A community mindset — You see customers as partners and coworkers as collaborators. You lift others up, always follow through on your commitments, and thrive in a team that does the same. (Community First)
• Momentum and ownership — You act with optimism, take initiative, and turn ideas into results. You move fast and bring others with you. (Fast Forward)
• Vision and boldness — You don’t just react — you anticipate. You think big, challenge the status quo, and push the work (and the industry) forward. (Ten Steps Ahead)
• Joy in the craft — You care deeply about what you build and how it makes people feel. You bring thoughtfulness, transparency, and a sparkling sense of humour to the table. (Delightful Work)

What You’ll Do

Here’s what you’ll do:

• 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 (e.g., Claude, Cursor, and embedded AI platforms)
• Set and maintain internal best practices for AI usage, data integrity, and privacy

What You Bring

• 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 (agentic workflows, AI platforms, prompt and agent configuration) and understanding how they integrate into business systems (APIs, data flows, human-in-the-loop design)
• Experience partnering with cross-functional leaders to translate strategic priorities into actionable roadmaps and navigating change management
• Comfort operating with ambiguity, with a focus on iterative execution, clear communication, and the judgment to separate practical value from hype
• Comfort working independently and asynchronously, while also prioritizing collaboration and connection with people
• Experience (or excitement for) working with AI
• Bonus: Experience leading internal communities of practice, change champions, or multi-department enablement programs

Compensation & Perks

We believe in fair, transparent compensation. Starting salary for this role is $130,000–$160,000, depending on previous experience and skillset, plus a 10% annual bonus opportunity based on company performance

New hires are expected to come in at the midpoint of this range. However, if this role sounds perfect for you and your expectations are outside of this range, we encourage you to apply and let us know in your application about your ideal package. If we agree that it’s a good fit, we will have open discussion around what’s possible.

Plus:

• Remote-first culture (with plenty of excellent in-person experiences sprinkled in)
• Company-wide closure between December 25th and January 1st
• Health and dental benefits, including a $1,000 healthcare spending account
• RRSP/TFSA contributions up to $3,000 a year (no employee contribution required!)
• Twice-yearly company wide summits (we call it HQ and you’ll love it)
• A delightful team of smart people who are good at what they do

Location

This role is open to candidates eligible to work in Canada (exception of Quebec désolé!).

We’re remote-first, but if you’re based in Toronto, even better. That’s where we were founded and where we maintain our HQ today!

A Bit More About Us

commonsku supports hundreds of promotional products distributors and suppliers with technology that drive efficiency, growth, and connection. Our skummunity (commonsku + community = skummunity, get it?) is powered by events, education, and shared knowledge and is core to who we are.

We’ve grown by being “for promo by promo” and now, we’re scaling our impact to elevating an entire industry. We’d love your help doing it.

A Note About AI

We use AI every day at commonsku to be faster and better. If you use AI tools to help you draft your resume or cover letter, that’s totally fine — just make sure what you submit reflects you.

In the spirit of transparency, we also use AI to help us work smarter. We utilize Teamtailor’s AI features to assist with applicant screening, note-taking, and interview recording. This technology helps us move quickly and efficiently, but it does not replace our judgment. A member of our Talent team reviews every resume and conducts every interview, ensuring that a human always makes the decision on who advances in our process.

commonsku is an Equal Opportunity Employer

We’re committed to building a diverse team that reflects the skummunity we serve. We welcome applicants of all backgrounds, experiences, and identities.