The Field Sales Enablement Manager at lightspeedhq is responsible for designing, delivering, and optimizing enablement programs to enhance the performance and productivity of Field Sales Teams across a region. This role partners with sales leadership and cross-functional teams to equip Field Account Executives with the skills, content, and knowledge needed to drive revenue growth and execute effectively in their territories.
What You'll Do
- Design, deliver, and optimize enablement programs that elevate the performance, productivity, and consistency of Field Sales Teams across a region
- Partner with Field Sales Leadership & Operations, cross-functional stakeholders, and subject matter experts to ensure Field Account Executives are equipped with the necessary skills, content, and knowledge
- Spend 50-75% of time traveling within the region to observe real customer interactions, conduct ride-alongs, and provide timely, actionable feedback
- Be a native speaker of the region to ensure full linguistic and cultural fluency
- Act as the Enablement Business Partner for the region
- Utilize on-the-ground analysis and deep understanding of the business landscape to identify gaps and prioritize opportunities
- Develop actionable solutions and proactively make recommendations to regional sales leadership
- Advocate for the region by building a compelling case for necessary resources and support
- Ensure alignment with the Enablement team
- Collaborate with the Enablement Team Manager to build and execute comprehensive enablement strategies focused on prospecting, territory management, solution selling, and deal closure
- Create and facilitate onboarding programs tailored to the needs of Field Sales Account Executives
- Design and deliver skill-development workshops using flipped classroom, roleplays, simulations, and field-based learning such as ride-alongs and in-territory coaching sessions
- Develop high-impact enablement assets including playbooks, territory planning frameworks, pitch decks, objection-handling guides, demo scripts, and customer conversation frameworks
- 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
- Provide targeted coaching to Field Sales Account Executives to strengthen prospecting, presentation, negotiation, and pipeline management capabilities
- Conduct regular ride-alongs and shadowing sessions
- Offer structured feedback immediately after customer meetings to reinforce best practices and drive behavioral change
- Build and maintain certification programs and competency models to ensure Field Sales teams meet performance standards and adhere to sales methodologies
- Contribute 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
What We're Looking For
- 3-5 years experience in delivering enablement programs for Field Sales, Outside Sales Teams, or Outbound Sales Motions
- 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
- Strong understanding of the Field Sales function, including prospecting strategies, territory management, solution selling, and deal progression
- 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
- Comfort with frequent travel and a hands-on coaching style that thrives in real-world field settings
Nice to Have
- Experience working in the field—travelling with reps, observing customer interactions, and delivering in-the-moment coaching
- Knowledge of hospitality industry and their unique sales considerations
Technical Stack
- Salesforce
Team & Environment
- Reports to: Senior Manager, Sales Enablement
Benefits & Compensation
- Frequent travel opportunity (50-75%)
- Inclusive and barrier-free workplace
- Accommodations available on request for candidates with disabilities
- Opportunity to work in a company founded on inclusion and diversity
- Workplace where everyone belongs
- Dual-listed on NYSE and TSX
- Global teams across North America, Europe, and Asia Pacific
- Serving businesses in over 100 countries
Work Mode
- Local position based in London
- 50-75% travel within the region required
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.
