System Enablement Specialist

Hi there! Thanks for stopping by

Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place!

We’re looking for a System Enablement Specialist to join our System Enablement team, part of our Information Systems department. You will be a strategic partner to our Go-to-Market (GTM) organization, acting as the essential bridge between our internal product team and go-to-market users.

In this role, your purpose is to directly impact sales effectiveness by creating and delivering high-quality enablement content. You will produce clear, practical, and engaging material designed to ensure our sales team can fully leverage the power of tools made available to them. The role also involves leading training sessions in both live and online formats to ensure this knowledge is successfully implemented.

As a critical conduit for feedback, gathering insights from the sales team and translating them into actionable recommendations for our IS Product team is critical. And finally, expert-level knowledge of our current system will ensure our internal tech stack continues to evolve.

What you’ll be responsible for:

• Designing, creating, and delivering highly engaging, multimedia training content including dynamic presentations, instructional videos, and practical guides that make complex information "stick."
• Leading engaging live and virtual training sessions on our CRM (Salesforce), sales engagement tools, and all new system functionalities, ensuring high levels of participation, adoption, and knowledge retention.
• Leveraging new and creative means to analyze and measure enablement impact, monitor tool adoption, and identify performance gaps, providing data-driven recommendations for improvement.
• Partnering with the Product Management team to ensure enablement activities align with scope and scale of initiatives and ensuring smooth coordination
• Acting as the critical bridge between technical/product teams and the GTM organization; mastering new features and technologies to translate their complexities into clear content for sales and other GTM Stakeholders.
• Managing multiple, simultaneous enablement projects from ideation to completion using tools like Jira and other task management tools. Drive the adoption of new features and processes across the company, ensuring a smooth transition for all sales teams and other GTM Stakeholders.

What you’ll be bringing to the team:

• A minimum of 2+ years of professional experience in Sales Enablement, Sales Operations, Technical Training, or a similar function where you’ve supported or improved sales teams.
• Hands on experience working with Salesforce CRM is required
• Proficiency with sales engagement tools such as Gong, along with a strong understanding of the broader sales tech ecosystem.
• Demonstrated experience with Google Workspace (Slides, Docs), and AI content creation tools (e.g., ChatGPT, Gemini, NotebookLM).
• Comfort using project management tools like Jira (or equivalent) for tracking tasks and workflows.
• Exposure to data analysis platforms such as Looker, Tableau, or similar tools.
• Excellent communication skills in English; French is considered an asset.
• Exceptional organizational abilities, with a proven capacity to adapt quickly in fast-changing or ambiguous environments.
• Strong collaboration skills, with experience partnering across internal teams to drive alignment and deliver results.
• Strategic thinking and problem-solving skills, with a proactive mindset toward anticipating challenges and shaping solutions.
• As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

Even better if you have, but not necessary:

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

About you:

• You are a master storyteller, capable of simplifying complex technical concepts into clear, engaging, and persuasive narratives for a sales audience.
• You possess an innate ability to quickly grasp complex technical features and a genuine passion for exploring new technologies, including AI tools and platforms.
• You don't just present; you create learning experiences. You have a creative flair for building content that is memorable, effective, and drives behavioral change.
• You are a proactive self-starter who thrives when working independently, but you are also a consummate team player who excels at cross-functional collaboration.

What is in it for you:

• Lots of autonomy, flexible work culture and the option of fully remote work
• Genuine career opportunities in a company that’s creating new jobs every day
• Opportunity to make a difference; help merchants grow their businesses and become more successful by creating or improving products and addressing customer feedback
• Work in a team big enough for growth but lean enough to make a real impact
• Development of very high traffic products, used at a global scale
• Opportunities to learn and expand your skill set
• Become a valued part of the diverse and inclusive Lightspeed culture

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

• Lightspeed equity scheme (we are all owners)
• Lunch provided in select offices on scheduled days
• Work from anywhere in the world for 60 days a year
• Health and wellness benefit, according to local eligibility
• Mental health online platform and counseling & coaching services
• Volunteer day