Regional Field Sales Enablement Manager, Lightspeed
More information about location
Point of Sale & commerce platform
Posted today
Point of Sale & commerce platform
1001+ employees
Posted today
More information about location
1001+ employees
Company mission
To bring the streets of our cities and communities to life by powering business owners with technology.
Role
Who you are
- 3-5 years experience in delivering enablement programs for Field Sales, Outside Sales Teams, Outbound 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 field sales enablement content and tools that drive behavioral change and performance improvement
- Experience working in the field—travelling with reps, observing customer interactions, and delivering in‑the‑moment coaching—is strongly preferred
- Strong understanding of the Field Sales function, including prospecting strategies, territory management, 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
What the job involves
- Reports to: Senior Manager, Sales Enablement
- The Field Sales Enablement Manager is responsible for designing, delivering, and optimizing enablement programs that elevate the performance, productivity, and consistency of the Field Sales Teams across a region
- This role partners with Field Sales Leadership & Operations, cross‑functional stakeholders, and subject matter experts to ensure that the Field Account Executives are equipped with the skills, content and knowledge needed to drive revenue growth and execute effectively in their territories
- This role requires extensive travel within the region [50-75%] , spending meaningful time in the field to observe real customer interactions, conduct ride‑alongs, and provide timely, actionable feedback and it necessitates being a native speaker of the region to ensure full linguistic and cultural fluency
- 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
- 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
- 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
Our take
Lightspeed provides restaurateurs and retailers with the simplest way to run their businesses at full potential. It helps entrepreneurs offer their customers positive and memorable experiences by taking care of the day-to-day management aspects of their business.
Around 75,000 businesses processing over $17 billion in transactions annually use Lightspeed’s restaurant POS software and omnichannel retail solution to manage inventory, customer preferences, sales and reporting — all from one centralised platform. Headquartered in Montreal, Lightspeeds team is distributed across North America, Europe and Asia Pacific, now serving over 150,000 locations worldwide.
Lightspeed POS maintains a unique edge over other companies of its type because it has secured the legal rights for the sole use of certain technologies. It has two registered patents in computing, calculating categories. These patents certify that Lightspeed POS is the sole owner of this intellectual property, which means that no other companies can use them.
Kirsty
Company Specialist at Welcome to the Jungle
Meet the team
45 people
Matthew Passmore, Field Implementation Team Lead
Insights
Company
Company benefits
- With Lightspeed PX, you can enjoy flexible paid time off and up to 2 months remote per year with our hybrid work policy
- 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, from #coffee_pals to sponsored sports teams
- Computer purchase program to get your personal Macbook
Company values
- We make it matter.
- We make it happen.
- We make it together.
- We make it human.
- We make it about the customer.
- We make it data driven.
Company HQ
Old Montreal, Montreal, QC
Articles
Leadership
Dax Dasilva
(Executive Chair)Founder of Never Apart, previously Developer of Bitmovers. Studied Computer Science, Art History, and Religious Studies at The University of British Columbia. Served as CEO for Lightspeed for 17 years until 2022.
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