Head of Mid Market and SMB Sales
Deliverect
Director of Sales Enablement
Alternative Payments
full-time
Posted on:
Location Type: Hybrid
Location: Toronto • 🇨🇦 Canada
Visit company websiteSalary
💰 CA$120,000 - CA$140,000 per year
Job Level
Lead
Tech Stack
Apollo
About the role
- Iterate and execute upon the company-wide enablement strategy across Sales, and GTM teams, focusing on onboarding, continuous learning, and performance optimization.
- Develop and launch structured onboarding programs that reduce ramp time and ensure every new hire is fully equipped to engage customers confidently.
- Build and maintain scalable sales playbooks, talk tracks, and certification programs that drive consistency across discovery, demo, and closing motions.
- Lead continuous training programs including weekly enablement sessions, deal coaching, product readiness updates, and competitive enablement.
- Partner closely with Sales leadership and RevOps to measure enablement ROI and link training initiatives directly to performance metrics (ramp time, win rate, conversion).
- Enable Customer Success teams through adoption, renewal, and expansion frameworks that strengthen customer relationships and drive NRR.
- Collaborate cross-functionally with Marketing, Product, and Operations to ensure alignment on messaging, positioning, and product knowledge.
- Own and optimize the enablement tech stack (LMS, Notion, Avarra.ai, Apollo) to deliver engaging, accessible training experiences.
Requirements
- 5 - 7+ years of experience in Sales Enablement, Revenue Enablement, or Sales Leadership roles (SaaS or FinTech preferred).
- Proven success designing and scaling enablement programs that reduce ramp time and improve conversion and win rates.
- Expertise in modern sales methodologies (Challenger, SPIN, GAP, or similar).
- Strong background in Sales and BDR enablement — with hands-on experience creating onboarding, playbooks, and certification programs.
- Excellent communication and facilitation skills, with executive presence and credibility across GTM teams.
- Experience working with enablement and sales tech tools (Salesforce/HubSpot, Apollo, LMS, Notion, Gong/Avarra).
- Strategic thinker who can also execute tactically — balancing long-term enablement strategy with immediate deliverables.
Benefits
- Competitive salary tailored to your experience, skills, and expertise.
- Equity opportunities so you can share in our growth and success.
- Unlimited PTO and flexibility when you need it the most.
- Yearly learning & development stipend to help you grow and do your best work.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard skills
Sales EnablementRevenue EnablementSales LeadershipOnboarding ProgramsSales MethodologiesPerformance OptimizationTraining Program DesignConversion ImprovementWin Rate ImprovementCustomer Relationship Management
Soft skills
Communication SkillsFacilitation SkillsStrategic ThinkingTactical ExecutionExecutive PresenceCredibilityCollaborationCross-Functional TeamworkCoachingAdaptability
