System Enablement Specialist

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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 in
Montreal, Quebec.
You will be a strategic partner to our Go-to-Market (GTM) organization, acting as the essential bridge between our technical teams and our sales teams and other GTM stakeholders.

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 materials designed to ensure our sales team can fully leverage our internal systems to meet and exceed their targets. You will be responsible for leading training sessions in both live and online formats to ensure this knowledge is successfully implemented.

Furthermore, you will act as a critical conduit for feedback, gathering insights from the sales team and translating them into actionable recommendations for our technical teams. This ensures our tools evolve to meet real-world needs. You will maintain expert-level knowledge of our current systems and will be given the opportunity to pioneer the use of new technologies, including leveraging AI to enhance our training and sales strategies.

What You'll Be Responsible For

• Content Creation & Delivery: Design, create, and deliver highly engaging, multimedia training content including dynamic presentations, instructional videos, and practical guides that make complex information "stick."
• Technical Liaison & Translation: Act as the crucial bridge between technical/product teams and the GTM organization. Master new features and technologies to translate their complexities into clear content for sales and other GTM Stakeholders.
• Training & Facilitation: Lead engaging live and virtual training sessions on our CRM (Salesforce), sales engagement tools (e.g., Gong), and all new system functionalities, ensuring high levels of participation and knowledge retention.
• Project & Change Management: Manage 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.
• Performance Analysis: Utilize analytics tools (e.g., Looker, Tableau) to measure training impact, monitor tool adoption, and identify performance gaps, providing data-driven recommendations to leadership

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), video editing software, 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.

Who You Are

• Exceptional Communicator: You are a master storyteller, capable of simplifying complex technical concepts into clear, engaging, and persuasive narratives for a sales audience.
• Technical Acuity & Curiosity: An innate ability to quickly grasp complex technical features and a genuine passion for exploring new technologies, including AI tools and platforms.
• Creativines: 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.
• Autonomous & Collaborative: 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.

Be a changemaker
You'll Enjoy

• A flexible work environment that empowers you to do your best work
• A culture that celebrates performance
• The chance to make an impact in a team that's big enough for career growth, but lean enough to make your voice heard
• Career-defining opportunities

Plus benefits designed to keep you happy, healthy and fulfilled.

• Flexible paid time off and remote work policies
• Equity options, because this is your company too
• Contributions to your pension plan. Your future matters
• Training opportunities to grow your skills and career
• Health and wellness credit so you feel your best
• Time off to volunteer and give back to your community
• Interest groups, employee led networks, social committees to sponsored sports teams
• Computer purchase program to get your personal Macbook
• Enhanced parental leave to support growing families

Fuel your growth. Find your people.

At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you—all within a driven, diverse and inclusive team that's passionate about empowering our communities

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.

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