AI Enablement Specialist

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Hi there! Thanks for stopping by 👋

Are you actively looking for a new opportunity? Or just exploring what’s out there in the world of AI and automation? Well… you might just be in the right place!

Lightspeed is seeking an AI Enablement Specialist, who will serve as the hands-on champion for our Enterprise Search & No-Code Agentic AI Platform. Reporting to the Head of IT, this hybrid role bridges technical implementation and business adoption, driving the cultural shift toward an Agent-Powered Workforce. You’ll deliver expert training, provide advanced technical enablement, and help teams identify and validate high-impact AI use cases through our AI Labs methodology.

What you’ll be responsible for:

• Supporting and enabling the successful adoption of Project Sidekick across the organization
• Providing Level 2/3 technical enablement for complex issues related to agent development, workflow logic, and tool integrations
• Assisting the business with platform configuration and connector integrations (e.g., Google Workspace, Slack, ServiceNow), ensuring permissions fidelity and accurate data ingestion
• Building, testing, and iterating on proof-of-concept (POC) No-Code Agents to demonstrate feasibility and business value
• Maintaining expert-level knowledge of the Agent Builder environment and interconnected productivity tools (e.g., Atlassian, Miro, Monday.com)
• Designing, developing, and delivering high-impact training curriculum focused on advanced Enterprise Search and agent utilization
• Training and managing a decentralized network of internal “AI Champions” to scale adoption across departments
• Partnering with P&C and Communications to execute internal marketing strategies that drive awareness and showcase successful use cases
• Facilitating AI Labs workshops, guiding teams through workflow mapping and pain point identification
• Validating and qualifying AI use cases by translating business needs into measurable, technically feasible Agent requirements
• Owning and prioritizing the Agentic AI backlog, aligning initiatives with high-value, repeatable tasks identified through AI Labs
• Contributing as part of the wider IT team to achieve organizational objectives, even when it extends beyond the immediate scope of the role

What you’ll be bringing to the team:

• Proven experience developing and training others on low-code/no-code automation platforms such as Glean, Relevance.ai, Zapier, Workato, or similar enterprise automation tools
• Deep familiarity with productivity and collaboration tools such as Slack, Google Workspace, Workday, Monday.com, Atlassian, and ServiceNow
• Exceptional public speaking, presentation, and curriculum development skills, with the ability to lead technical workshops for non-technical audiences
• Strong conceptual understanding of API integrations, data indexing, and cloud environments (e.g., GCP)
• Demonstrated ability to analyze and map business processes to define measurable automation opportunities
• Strong problem-solving acumen with an ownership mindset
• Clear and approachable communication style, able to translate technical concepts into practical business value
• Ability to work and contribute as part of a globally distributed team
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

Nice to have:

• Experience supporting enterprise search platforms or internal AI copilots
• Background in business process optimization or digital transformation initiatives
• Experience building internal communities of practice or champion networks

What’s in it for you?

• Ability to do your job in a truly flexible environment
• Exposure to modern and proven AI and automation technologies
• Opportunity to shape how an Agent-Powered Workforce operates at scale
• Opportunity to join a fast-paced, high-growth company
• Tons of growth opportunities into technical, strategic, or people leadership roles
• Work in a team big enough for growth but lean enough to make a real impact

… and enjoy a range of benefits that’ll keep you happy and healthy and (not) hungry:

• Lightspeed RSU program (we are all owners)
• Unlimited paid time off policy
• A variety of snacks, coffee, and teas are always accessible and available in the office kitchen — and on Tuesdays, Wednesdays, and Thursdays lunch is served
• Paid leave assistance for new parents
• Flexible working policy
• Health insurance
• People Experience — work from pretty much anywhere in the world for 60 days a year
• Health and wellness benefits
• LinkedIn Learning
• Volunteer day

#LI-SS3

At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skill set, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the total compensation for this position to be in the range of *$85k-100k CAD*. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, RRSP plan and match, paid parental leave top-up, and paid time off.

Please note that this compensation information is solely for candidates hired to perform work within Ontario and reflects the amount Lightspeed is willing to pay at the time of this posting. This role represents an *existing vacancy at Lightspeed. Lightspeed uses artificial intelligence–enabled tools to support certain aspects of the recruitment process; all hiring decisions are made by our recruiting and hiring teams.*

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes. If we have not directly engaged your company in writing to supply candidates for a specific vacancy, Lightspeed will not be responsible for any fees related to unsolicited resumes.

Lightspeed is a proud equal opportunity employer and we are committed to creating an inclusive and barrier-free workplace. Lightspeed welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

Where to from here?

Obviously, this has to be mutually beneficial: we want you to step into a role you love, and we want to offer you a place you’re proud to come to every day. For a glimpse into our world check out our career page here.

Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that. We were founded in 2005, in Montreal’s gay village and our original members were all part of the LGBTQ+ community. The ethos of our business has been about inclusion from the very beginning, and we strive to provide a workplace where everyone belongs.

Who we are:

Powering the businesses that are the backbone of the global economy, Lightspeed's one-stop commerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences. Our cloud commerce solution transforms and unifies online and physical operations, multichannel sales, expansion to new locations, global payments, financial solutions, and connection to supplier networks.

Founded in Montréal, Canada in 2005, Lightspeed is dual-listed on the New York Stock Exchange (NYSE: LSPD) and Toronto Stock Exchange (TSX: LSPD). With teams across North America, Europe, and Asia Pacific, the company serves retail, hospitality, and golf businesses in over 100 countries.

Lightspeed handles your information in accordance with our Applicant Privacy Statement.