Director - Revenue Enablement

2 weeks ago


Canada GP Strategies Full time $120,000 - $200,000 per year

Job Summary / Overview:

The Director, Revenue Enablement is accountable for driving measurable sales productivity and revenue acceleration by designing, delivering, and optimizing enablement programs that empower revenue teams to win more deals across all market segments. This role translates go-to-market strategy into actionable learning experiences, tools, and resources that directly improve seller performance and customer engagement outcomes.

This is a hands-on leadership role that partners closely with Sales Leadership, Marketing, and RevOps to deliver comprehensive enablement solutions that reduce ramp time, increase deal velocity, and strengthen value-based selling capabilities across the organization. The role requires deep expertise in creating both human-consumable and machine-readable content, ensuring our revenue teams and AI-powered tools work seamlessly together to maximize customer value delivery.

Key responsibilities include developing and managing enablement content architecture for both human sellers and agentic AI systems; leading a distributed team of Revenue Enablement Leads; delivering impactful training programs to global audiences across multiple time zones and cultures; serving as the primary voice of sales in all GTM feature releases and product launches; orchestrating Sales Advisory Councils and feedback mechanisms; driving adoption of consultative and solution-selling methodologies; and ensuring successful account pursuit strategies across deal sizes ranging from transactional to complex seven-figure enterprise agreements.

Additionally, as a critical responsibility, the Director ensures all revenue teams are equipped to leverage AI-augmented selling tools effectively, including developing frameworks for prompt engineering, validating AI-generated customer insights, and establishing governance for AI-assisted customer interactions while maintaining authentic human relationships.

Impacts:

Decrease Time to First Deal and Overall Ramp Time for new sellers

Increase Win Rate % and Average Deal Size across all segments

Improve Seller Productivity (Revenue per Rep) and Quota Attainment %

Increase adoption and ROI of sales methodology and enablement programs

Accelerate deal velocity and reduce sales cycle length

Required Qualifications:

7+ years of experience in Revenue Enablement, Sales Training, or Sales Leadership roles

Proven track record of building and scaling enablement programs that demonstrably impact revenue metrics

Experience managing and developing distributed or remote teams

Strong experience designing and delivering training programs to global, culturally diverse audiences with varying levels of expertise

Deep expertise in consultative and solution-selling methodologies with hands-on experience enabling complex enterprise deals ($1M+) as well as high-velocity transactional sales

Experience designing content taxonomies and governance frameworks for both human consumption and API/system integration

Demonstrated ability to create and validate AI training data sets, design prompt libraries for sales use cases, and establish quality assurance processes for AI-generated content

Strong analytical skills with experience measuring enablement impact and ROI using data from CRM and sales performance platforms

Excellent facilitation and presentation skills with experience running executive-level workshops and advisory councils across multiple regions and time zones

Strong cross-functional collaboration skills with proven ability to influence without authority

Experience with change management and driving adoption of new processes, tools, and methodologies at global scale

Understanding of modern revenue technology stack and how enablement integrates across the customer journey

Ability to adapt training delivery methods for virtual, hybrid, and asynchronous learning environments

Preferred Qualifications:

Industry-relevant experience to GP's businesses

Experience working with geographically distributed sales teams across EMEA, APAC, and Americas

Experience in B2B SaaS or technology companies with recurring revenue models

Certification or working experience in recognized sales methodologies (e.g., MEDDIC, Challenger, Sandler, Value Selling)

LI-JM1
LI-REMOTE

  • , PE, Canada Affirm Full time

    Senior Director, Revenue Enablement 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,...


  • , , Canada Affirm Full time

    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...


  • , , Canada Revaly Full time

    About the Role This is a foundational hire. As Director, GTM Enablement you’ll build the systems, training, and insights that turn potential into performance. Your focus: sales enablement: designing the structure, tools, and content that help our revenue teams ramp faster, sell smarter, and deliver measurable results. You’ll be hands‑on from day one,...


  • , PE, Canada Affirm Full time

    A leading financial technology company seeks a Senior Director of Revenue Enablement to develop strategic initiatives that drive performance across all customer-facing teams. The ideal candidate will have over 15 years of experience in enablement organizations and proven leadership skills. This role offers a competitive salary range of $225,000 – $295,000...


  • , , Canada Affirm Full time

    A financial technology company is seeking a strategic leader for their Global Revenue Enablement organization. The role emphasizes building programs that drive performance and productivity across customer-facing teams. The ideal candidate should have extensive experience in enablement strategy and possess strong storytelling and analytical skills. This...


  • , , Canada Affirm Full time

    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...


  • , , Canada Motive Full time

    A leading SaaS company in Canada is seeking a Director of Enablement Business Partners to lead a team focused on sales enablement for Mid-Market, Commercial, and SMB segments. This role involves strategy development, performance management, and collaboration with stakeholders to enhance the effectiveness of sales training. The ideal candidate has over 10...


  • , , Canada Revaly Full time

    A software development company in Toronto seeks a Director of GTM Enablement to build sales enablement systems and training. This role involves designing onboarding and training programs, measuring enablement impact, and collaborating with various teams. Ideal candidates will have 6+ years in Revenue Operations or Sales Enablement in B2B SaaS and fintech...


  • , , Canada Motive Full time

    Who we are: Motive empowers the people who run physical operations with tools to make their work safer, more productive, and more profitable. For the first time ever, safety, operations and finance teams can manage their drivers, vehicles, equipment, and fleet related spend in a single system. Combined with industry leading AI, the Motive platform gives you...


  • , , Canada Motive Full time

    Director, MCS Enablement Business Partners Who we are: Motive empowers the people who run physical operations with tools to make their work safer, more productive, and more profitable. For the first time ever, safety, operations and finance teams can manage their drivers, vehicles, equipment, and fleet related spend in a single system. Combined with industry...