Insight GlobalVerified Job Source

System Trainer

St. Jacobs, ON
On-site
Posted Sep 27, 2026
1 position

$40–$45 / hour

Opens an external site

Employment type: Contract
Experience level: Mid-level · 2+ years
Apply by: Oct 25, 2026
Posting language: English
Working hours: 40 hours per week
Seniority: Mid-Senior level
Application method: Direct apply is available

Job summary

Deliver virtual and onsite training to support the rollout of a new POS system across retail locations, and coach end users to encourage successful adoption. Assess training needs with store leaders and project stakeholders, and provide hands-on support during post-go-live activities.

Job details

Role: POS System Trainer Type: 6 month contract Location: Onsite in St. Jacobs, ON (travel across Ontario after 1 month) Rate: $40-$45/hr JOB DESCRIPTION Insight Global is looking for a POS System Trainer for one of Canada's largest independent retailers. This individual will play a key role in supporting the rollout of a new Point-of-Sale (POS) system across store locations by delivering engaging training, coaching end users, and driving successful adoption. The trainer will work closely with store leadership and project stakeholders to assess training needs, facilitate both virtual and onsite training sessions, and provide hands-on support during post-go-live activities. This role requires frequent travel across Canada and flexible work hours. REQUIRED SKILLS AND EXPERIENCE - Retail operations experience - Knowledge and understanding of POS systems - Training & Development experience (creating and delivering end-user training programs) - Willing to travel frequently across Ontario and Alberta and flexible schedule - Strong communication and presentation skills NICE TO HAVE SKILLS AND EXPERIENCE - Post-go-live support experience (floor support, coaching, issue triage, hypercare/warranty support) - Stakeholder engagement skills (working with store leaders, project teams, and end users) We may use artificial intelligence tools to assist with the screening, assessment, or selection of potential applicants for this position. Vacancy: This posting is for a currently vacant role, and the successful candidate will be hired into an existing open position.

What you’ll do

Requirements

Candidates need retail operations experience, knowledge of POS systems, and experience creating and delivering end-user training programs. Strong communication and presentation skills, willingness to travel frequently across Ontario and Alberta, and schedule flexibility are required; post-go-live support and stakeholder engagement experience are preferred.