System Enablement Specialist (AI)

TL;DR

System Enablement Specialist (AI): Creating and delivering high-quality enablement content for the Go-to-Market (GTM) organization with an accent on sales effectiveness by ensuring sales teams can fully leverage internal systems. Focus on translating technical complexities into clear content and pioneering the use of new AI technologies for training and sales strategies.

Location: Onsite in Montreal, Quebec, Canada

Company

Lightspeed is a global commerce platform helping merchants simplify, scale, and provide exceptional customer experiences, founded in Montreal, Canada.

What you will do

• Design, create, and deliver highly engaging multimedia training content, including presentations, videos, and guides.
• Act as a crucial bridge between technical/product teams and the GTM organization, translating complex features into clear content.
• Lead engaging live and virtual training sessions on CRM (Salesforce) and sales engagement tools.
• Manage multiple, simultaneous enablement projects from ideation to completion using tools like Jira.
• Drive the adoption of new features and processes across the company, ensuring smooth transitions for sales teams.
• Utilize analytics tools such as Looker and Tableau to measure training impact and identify performance gaps.

Requirements

• Minimum of 2+ years of professional experience in Sales Enablement, Sales Operations, Technical Training, or a similar function.
• Hands-on experience working with Salesforce CRM is required.
• Proficiency with sales engagement tools such as Gong and a strong understanding of the broader sales tech ecosystem.
• Demonstrated experience with Google Workspace, video editing software, and AI content creation tools.
• Comfort using project management tools like Jira.
• Exposure to data analysis platforms such as Looker or Tableau.
• Excellent communication skills and fluency in English are required.
• Exceptional organizational abilities and strong collaboration skills.

Nice to have

• A solid understanding of the product development lifecycle and experience within a technology-focused organization.
• Familiarity with the Hospitality and/or Retail industries.

Culture & Benefits

• A flexible work environment and remote work policies.
• Equity options and contributions to your pension plan.
• Training opportunities to grow your skills and career.
• Health and wellness credit.
• Time off to volunteer and give back to your community.
• Interest groups, employee-led networks, social committees, and sponsored sports teams.
• Computer purchase program to get your personal Macbook.
• Enhanced parental leave to support growing families.