Director of Sales Enablement

At Alternative Payments, we are transforming the way service-based companies handle payments. Our innovative platform automates the entire accounts receivable process, helping businesses save time, reduce costs, and scale with confidence.

We are building a global team that values innovation, impact, and collaboration. As part of a scaling FinTech company, every person on our team has the opportunity to shape our future, influence our products, and make a real difference for our customers.

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!

• 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.

• 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.

• 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.

Compensation: The total compensation range for this role is $120,000 - $140,000 CAD, plus equity. The range displayed on each job posting reflects the approximate total target compensation for the position. Within the range, individual pay is determined by factors including relevant skills, experience, education/training.

At Alternative Payments, you’ll do work that truly matters.

• Own your impact: Lead meaningful, high-impact projects and collaborative initiatives that are shaping the future of FinTech and redefining how businesses get paid.

• Collaborate: Work with a diverse, innovative team where every voice is heard and great ideas come from anywhere.

• Grow with us: Your career journey is top of mind. We prioritize internal growth and give you the space to shape your path based on your goals — whether that’s deepening your expertise in your domain or exploring something new.

• Thrive in a supportive culture: As a scaling start-up, there’s a lot to be done and initiative is key. We believe in shared learning, open communication, and building each other up. When one of us grows, we all do.

• 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.

• Transparency & Honesty: We operate openly and build trust with customers, investors, and teammates.

• Dependability: We do what we say we will, consistently and reliably.

• Partnership: We collaborate across teams and with clients to solve big problems.

• Revolutionary & Boldness: We challenge norms to create stronger, safer, and simpler solutions.

• Diversity & Inclusion: We embrace different perspectives to build stronger teams and a more inclusive workplace.

We’re looking for candidates who are ready to step in and make an impact from day one. We know that sometimes people hold back unless they meet every requirement, but if you’re excited about the role, bring relevant experience, and are ready to contribute, we want to hear from you!

All resumes are reviewed by our small but mighty talent team. While we may use AI tools to help prioritize applications, real people are behind every resume review and hiring decision. We’re also committed to an inclusive and accessible process. If you require reasonable accommodation during the hiring process, please let us know upon being selected to interview.