Sales Enablement Manager

Purpose of the Role

Regional Enablement Implementation

The Sales Enablement Manager is responsible for designing, delivering, and optimizing enablement programs that elevate the performance, productivity, and consistency of the Sales Teams across a region. This role partners with Sales Leadership & Operations, cross‑functional stakeholders, and subject matter experts to ensure that the SDRs and Account Executi ves are equipped with the skills, content and knowledge needed to drive revenue growth and execute effectively in their territories.

Regional Enablement Partnership

Act as the Enablement Business Partner for the region and by utilizing your “on-the-ground” analysis and deep understanding of the business landscape identify gaps, prioritize opportunities, and develop actionable solutions and proactively make recommendations to regional sales leadership. Advocate effectively for your region by building a compelling case for necessary resources and support, ensuring alignment with the Enablement team.

Key Responsibilities

Enablement Strategy & Program Development

Collaborate with the Enablement Team Manager to build and execute comprehensive enablement strategies focused on prospecting, territory management, solution selling, and deal closure.

Training Design & Delivery

Create and facilitate onboarding programs tailored to the needs of Field Sales Account Executives, and skill‑development workshops focused on converting knowledge into skills through flipped classroom, roleplays, simulations, and field‑based learning such as ride‑alongs and in‑territory coaching sessions.

Content & Tools Creation

Develop high‑impact enablement assets—including playbooks, territory planning frameworks, pitch decks, objection‑handling guides, demo scripts, and customer conversation frameworks—to support consistent and effective selling.

Cross‑Functional Collaboration

Partner with Product, Marketing, Operations, and regional Sales Leadership to ensure alignment in messaging, product positioning, and go‑to‑market strategies across territories and segments.

Coaching & Performance Support

Provide targeted coaching to Field Sales Account Executives to strengthen prospecting, presentation, negotiation, and pipeline management capabilities. Conduct regular ride‑alongs and shadowing sessions, offering structured feedback immediately after customer meetings to reinforce best practices and drive behavioral change.

Certification & Competency Frameworks

Build and maintain certification programs and competency models to ensure Field Sales teams meet performance standards and adhere to sales methodologies.

And a little bit of....

• Contributing as part of the wider team to achieve organisational objectives even if this means doing things that aren’t strictly within the scope of your role.

KPI's

Enablement Outputs related:

• Certification Success Rate: High pass rates for new hires and current team members on role-specific certifications.

• Onboarding Completion Rate: Ensuring new hires complete all training and are certified within expected timelines.

• Participant Satisfaction Score: High feedback scores reflecting relevance and quality of training programs.

• Knowledge Retention and Application: Evidence of skill application in daily work through follow-up evaluations and manager feedback.

• Training Quality and Engagement: Regular improvements to training materials based on feedback, resulting in increased engagement and knowledge retention.

Business Outcomes related:

• Influence role-specific KPIs, such as: including pipeline generation [#SQLs], conversion rates [ #demos; meetings held], average deal size, sales cycle length—to measure program impact and progress against goals.

Experience

• 3-5 years experience in delivering enablement programs for Sales Motions, preferably in global SaaS companies;

• Experience in evaluating the effectiveness of enablement programs and their impact on business critical metrics such as pipeline growth, win rates, quota attainment, and revenue generation;

• Experience in working with data to extract useful, actionable insights;

• Proven track record of creating sales enablement content and tools that drive behavioral change and performance improvement.

Experience working with reps, observing customer interactions, and delivering in‑the‑moment coaching—is strongly preferred.

Attributes & Skills

What will help you kick ass in this role?

• Strong understanding of the inbounds Sales function, prospecting, qualification, solution selling, and deal progression;

• Knowledge of hospitality industry and their unique sales considerations is a plus;

• Ability to extract actionable insights from data and clearly articulate these insights to stakeholders;

• Excellent presentation and facilitation skills with the ability to engage and influence at all levels;

• Strong content creation skills to develop compelling enablement materials tailored for field environments;

• Understanding of sales methodologies, CRM systems (particularly Salesforce), and sales technology;

• Collaborative mindset with the ability to work cross-functionally across multiple teams and time zones;

• Strategic thinking combined with attention to detail in program execution;

• Adaptable and entrepreneurial approach to enablement in fast-paced, target-driven environments.

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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