Senior Director, Revenue Enablement

Affirm; Canada; Remote; CAD 225,000 - 295,000; Full time

Job summary

A leading financial technology company is seeking a strategic leader to head their Revenue Enablement organization. This role emphasizes driving performance and growth across customer-facing teams in a remote capacity within Canada. The ideal candidate should possess extensive experience in enablement strategy and a proven ability to empower and develop teams to exceed targets. The compensation ranges from $225,000 to $295,000 annually, including benefits such as generous health care coverage and flexible spending wallets.

Benefits

Health care coverage

Flexible Spending Wallets

Competitive vacation schedules

Employee stock purchase plan

Qualifications

• 15+ years of professional experience in fast-paced environments.
• Demonstrated impact on business outcomes through analytics.
• Experience in implementing sales methodologies like MEDDPICC.

Responsibilities

• Lead development and execution of go-to-market strategies.
• Design engaging learning experiences for field teams.
• Improve enablement analytics and ensure KPI visibility.

Skills

Leadership in multidisciplinary enablement organizations

Strategic and analytical mindset

Excellent communication and storytelling skills

Deep expertise in enablement frameworks

Collaborative work style

Empathetic leadership

Tools

Gong

Spekit

ChatGPT

Job description

Affirm is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest.

Affirm is seeking a strategic, data-driven, and collaborative leader to head our Global Revenue Enablement organization, driving performance, productivity, and growth across all customer-facing teams. This individual will be responsible for defining and executing a unified enablement strategy that accelerates seller readiness, strengthens cross‑functional alignment, and elevates execution across the entire revenue lifecycle. The ideal candidate will bring deep expertise in enablement strategy, storytelling, and data‑driven performance management – building programs that empower teams, improve outcomes, and amplify Affirms value proposition across markets and channels.

What you’ll do

We are looking for a strategic, data‑driven, and collaborative leader to head our Revenue Enablement organization, driving revenue‑wide performance, productivity, and growth across all customer‑facing functions. Key responsibilities include:

• Lead the development and execution of a unified go‑to‑market strategy, aligning Product, Pricing, Legal, and Revenue priorities. Shape the storytelling and positioning that bring the Affirms narrative to life across verticals and channels.
• Develop and lead a global enablement strategy and team that accelerates seller readiness and ramp time, drives revenue attainment, and delivers scalable onboarding, continuous learning, and leadership programs. Drive programs supporting internal Revenue teams and external merchant and partner audiences.
• Design inclusive and engaging learning experiences for internal field teams and external merchant and partner teams using a mix of in‑person, virtual, and on‑demand formats that reflect adult learning principles and encourage continuous skill growth.
• Oversee and continuously improve enablement analytics and dashboards, ensuring visibility into KPIs that connect training, readiness, and performance outcomes.
• Leverage enablement technology, learning systems, and AI‑driven tools to improve efficiency and scale, using best‑in‑class platforms such as Gong, Spekit, ChatGPT, and other AI solutions. Own and deliver program playbooks to drive operational effectiveness.
• Foster a supportive, inclusive, and empowering team culture that values curiosity, collaboration, and continuous improvement.

What we look for

• Proven leadership in multidisciplinary enablement organizations, with 15+ years of professional experience and 10+ years of experience building and scaling teams in fast‑paced, high‑growth, or enterprise environments.
• Demonstrated impact on business outcomes, including reducing ramp time, improving win rates, increasing attainment, and strengthening retention and engagement.
• Strategic and analytical mindset, with the ability to set vision and strategy across multiple functions while driving executional excellence, defining KPIs, evaluating program effectiveness, and communicating insights that inform executive decisions.
• Excellent communication and storytelling skills, able to connect data, strategy, and vision into compelling narratives that inspire action.
• Deep expertise in enablement frameworks and sales methodologies (e.g., MEDDPICC, Challenger), with experience implementing and driving adoption across field organizations.
• Collaborative and communicative work style, with a bias for action and proven track record of proactively partnering across teams to achieve shared outcomes in a highly matrixed, complex, and consensus‑driven environment.
• Empathetic and supportive leader who develops, empowers, and celebrates diverse teams to perform at their best.

Location - Remote Canada

Remote (Canada)

If you have follow‑up questions after you’ve applied directly to the role, please reach out to [e-mail]. We kindly ask that you refrain from contacting senior leaders directly so our recruiting team can help ensure a more efficient, streamlined, and equitable process for all candidates.

Pay & Equity

Base Pay Grade: U

Equity Grade: 8

CAN base pay range per year: $225,000 – $295,000

Affirm focuses on providing a simple and transparent pay structure which is based on a variety of factors, including location, experience and job‑related skills.

Base pay is part of a total compensation package that may include equity rewards, monthly stipends for health, wellness and tech spending, and benefits (including 100% subsidized medical coverage, dental and vision for you and your dependents).

Benefits

• Health care coverage – Affirms covers all premiums for all levels of for you and your dependents
• Flexible Spending Wallets – generous stipends for spending on Technology, Food, various lifestyle needs, and family‑forming expenses
• Time off – competitive vacation and holiday schedules allowing you to take time off to rest and recharge
• ESPP – An employee stock purchase plan enabling you to buy shares of Affirms at a discount

Affirm is proud to be a remote‑first company! The majority of our roles are remote and you can work almost anywhere within the country of employment. Affirmsers in proximal roles have the flexibility to work remotely, but will occasionally be required to work out of their assigned Affirms office. A limited number of roles remain office‑based due to the nature of their job responsibilities.

We believe It’s On Us to provide an inclusive interview experience for all, including people with disabilities. We are happy to provide reasonable accommodations to candidates in need of individualized support during the hiring process.

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