Learning Enablement Manager Jobs in Toronto, ON (NOW HIRING)

Your Role as a Sales Enablement Manager: 

The Sales Enablement Manager will serve as the connective tissue between Marketing, Product Marketing, and the Sales organization. You will own the programs, content, and processes that equip our revenue teams to effectively engage prospects, navigate competitive situations, shorten sales cycles, and increase win rates.

This role works in close partnership with Sales Leadership, Product Marketing, Revenue Operations, and Customer Success to build a scalable and sustainable enablement engine.

A Day in the Life of an Sales Enablement Manager: 

Enablement Strategy & Program Ownership

• Design and own the Appspace sales enablement roadmap, aligned to pipeline, win rate, and ramp time goals
• Establish and run a regular enablement cadence: onboarding programs, ongoing training, deal clinics, and competitive review sessions
• Define success metrics for enablement (ramp time, deal velocity, win rate by segment, content usage) and report out to Sales and Marketing leadership
• Partner with Sales Leadership to identify skill gaps and translate them into structured learning programs

Content Development & Management

• Build and maintain a centralized, well-organized sales content library - pitch decks, discovery guides, objection handling frameworks, ROI tools, and competitive battlecards
• Translate complex product capabilities and positioning (developed by Product Marketing) into compelling, rep-friendly sales narratives and talk tracks
• Create role-specific content for different sales motions: new logo acquisition, expansion/upsell, enterprise deals, and channel/partner sales
• Audit existing content inherited from Product Marketing; rationalize, refresh, and retire to ensure reps are using current, accurate materials
• Own the sales content management system and governance, tagging, analytics, and adoption

Onboarding & Ramp Programs

• Collaborate with sales leadership to redesign sales onboarding for new AEs, SDRs, and SEs - targeting a measurable reduction in time-to-first-deal
• Build structured paths covering product knowledge, sales methodology, competitive landscape, and value-based selling
• Develop a manager enablement track to ensure frontline managers are coaching to consistent methodology and playbooks

Sales Process & Methodology

• Embed and reinforce a consistent sales methodology (e.g., MEDDIC/MEDDPICC, Challenger, Command of the Message) across the sales organization
• Build deal qualification and progression frameworks that align to Appspace's ICP and buying committee dynamics
• Partner with Revenue Operations to align enablement programs to CRM stage definitions and pipeline inspection processes
• Leverage win/loss analysis to identify coaching opportunities and inform content priorities

Competitive Intelligence & Readiness

• Own distribution and knowledge verification of competitive enablement, leveraging up-to-date battlecards and competitive positioning for key competitors
• Work with Product Marketing to rapidly disseminate competitive intelligence when market dynamics shift
• Train reps on how to navigate competitive objections and position Appspace's differentiation confidently

Product Launch & Campaign Readiness

• Lead field readiness for new product launches, packaging changes, and pricing updates - ensuring reps can speak to new capabilities on day one
• Partner with Demand Generation to align on campaign messaging and ensure sales can follow up with consistency
• Build and maintain updated talk tracks, email templates, objection handling, and customer-facing collateral to support new product and feature launches

Cross-Functional Collaboration

• Serve as the primary liaison between Sales and Marketing - translating field feedback into product marketing and campaign inputs
• Work with Customer Success to leverage customer stories, use cases, and expansion motions as sales assets
• Partner with RevOps on tooling, workflow automation, and data that supports rep productivity and enablement effectiveness

What You'll Need: 

• 5-8 years of experience in Sales Enablement, Product Marketing, or a field-facing role in B2B SaaS
• Demonstrated experience building or scaling a sales enablement function, not just executing within one
• Strong content creation skills - you can write a crisp battlecard, a punchy pitch deck, and a structured discovery guide
• Experience with a recognized sales methodology (MEDDPICC, Challenger, Command of the Message, or similar)
• Comfortable with sales content management platforms (Highspot, Seismic, Guru, or equivalent)
• Data-driven mindset - you track what you build and use results to iterate
• Exceptional communication and facilitation skills - you can hold a room of skeptical enterprise reps
• Experience in a $50M-$200M ARR B2B SaaS company, ideally with both SMB and enterprise sales motions

Nice to Have:

• Experience in the employee communications, digital workplace, or workplace technology space
• Familiarity with Salesforce, Gong, Groove, or similar sales tech stack tools
• Prior experience as a quota-carrying AE or SDR
• Experience enabling both direct and channel/partner sales motions

The Perks of Working for Appspace:

For all our Canadian based team members, we offer a variety of benefits from competitive salaries, medical, dental and vision coverage, ongoing training opportunities, gym membership reimbursement, mental health resources, and a fully paid maternity and parental leave program. 

• Generous PTO
• 5 additional days off for training 
• Flexible work schedules
• Remote work opportunities
• Appspace Quiet Fridays (No non-essential internal meetings scheduled)
• Paid company holidays