Director of Sales Enablement

Alternative Payments is a leading payments platform for service-based companies. Our innovative platform enables businesses to automate the entire accounts receivable process and reduce the overall expense of payment processing. We are dedicated to fostering growth and providing exceptional value to our clients.

Job Summary

We’re seeking a Director of Sales Enablement to join our Sales team and build the foundation for a world-class enablement function that empowers our Sales, BDR, Partnerships, and Account Manager teams to perform at their highest potential.

Reporting to the VP of Sales, this role is ideal for someone who thrives in a builder environment, loves creating structure and clarity at scale, and wants to take a hands‑on leadership role in shaping how we sell, train, and grow. You’ll partner directly with our sales and cross‑functional leaders to design, launch, and scale enablement programs that accelerate ramp time, improve win rates, and strengthen our go‑to‑market engine.

This is a hybrid position based in Toronto. We are in the downtown office Monday, Tuesday and Wednesday

Responsibilities

- 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.

Nice to Haves

- Experience working in FinTech, SaaS, or startup environments with high‑growth revenue teams.
- Understanding of the payments space or MSP ecosystem; candidates without this experience should demonstrate the ability to ramp quickly in a complex, technical domain.
- Familiarity with sales certification programs, readiness assessments, or performance analytics dashboards.
- History of partnering closely with executive teams to influence GTM strategy and process improvement.
- Comfort operating in a fast‑paced, dynamic environment where enablement strategy and execution evolve rapidly.

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