Director, GTM Enablement

Accountabilities:

• Act as a strategic thought partner to GTM leadership, translating early observations, performance concerns, and business priorities into clearly diagnosed problems, practical solutions, and measurable enablement programs.

• Diagnose performance gaps using funnel data, conversation intelligence, rep feedback, manager input, and collaboration with Revenue Operations, identifying the specific behaviors or process gaps affecting performance.

• Build and own scalable onboarding programs for new GTM hires, with a clear focus on accelerating ramp time and ensuring new team members develop the knowledge, skills, and confidence required to perform effectively.

• Develop sharp, practical messaging and positioning that sellers can confidently use in customer conversations, collaborating with Marketing and technical subject matter experts to translate complex offerings into compelling sales narratives.

• Design and deliver enablement programs across the full GTM lifecycle, including pipeline generation, discovery, stage conversion, deal progression, customer onboarding, retention, expansion, and post-sale effectiveness.

• Launch programs in partnership with functional leaders, establishing structured checkpoints, adoption measures, and success metrics from the beginning and continuously evaluating their impact on business performance.

• Equip Sales, BDR, and Customer Success managers with the frameworks, tools, and coaching approaches required to reinforce and sustain enablement programs after launch.

• Build and lead the enablement organization, establishing the strategy and operating model for technical enablement, field coaching, and broader GTM capability development.

• Use conversation intelligence platforms such as Gong or Chorus to review calls, identify patterns, and translate observations into targeted coaching plans and performance improvements.

• Measure enablement initiatives against rep performance and business outcomes, continuously improving successful programs and discontinuing initiatives that fail to deliver meaningful impact.

Requirements

• 6-8+ years of experience across sales, sales leadership, enablement, training, instructional design, or related functions, ideally including experience within B2B SaaS.

• Sufficient experience working directly within or alongside revenue organizations to establish credibility with sales and customer-facing teams from day one.

• Demonstrated experience managing, mentoring, or developing people, with the ability to build a high-performing enablement function as the team grows.

• Proven track record of designing and delivering enablement programs that generated measurable improvements in rep performance, productivity, conversion, ramp time, or other business outcomes.

• Hands-on experience with conversation intelligence platforms such as Gong or Chorus, including the ability to independently review calls, identify recurring patterns, and turn findings into actionable coaching programs.

• Strong ability to work directly with funnel and performance data, either independently or in partnership with Revenue Operations, and use quantitative insights to guide enablement priorities.

• Strong understanding of sales processes, methodologies, full-funnel metrics, and the factors that influence pipeline generation, conversion, deal progression, onboarding, retention, and expansion.

• Experience enabling post-sale teams such as Customer Success, or a demonstrated willingness and ability to expand enablement beyond the sales organization.

• Excellent communication, facilitation, writing, and stakeholder management skills, with the ability to work effectively with frontline representatives, managers, executives, and cross-functional partners.

• Strong ability to write positioning and messaging from the ground up rather than simply package existing marketing materials.

• Comfortable working with complex or technical products and partnering with subject matter experts to translate technical concepts into practical, customer-facing guidance.

• Entrepreneurial and highly autonomous mindset, with the initiative to identify problems, form a point of view, build solutions, and drive implementation without waiting for detailed specifications.

• Data-driven, diagnostic approach with strong problem-solving skills and a focus on building programs that create lasting organizational capability.

Benefits

• Opportunity to lead and shape the GTM enablement strategy across Sales, BDR, and Customer Success.

• High-impact leadership position with direct influence on rep performance, ramp time, pipeline conversion, and broader revenue outcomes.

• Opportunity to build and develop an enablement team spanning technical enablement and field coaching.

• Cross-functional exposure and collaboration across Sales, BDR, Customer Success, Marketing, and Revenue Operations.

• Significant autonomy to identify business problems, design solutions, and establish scalable enablement programs.

• Opportunity to work in a growing B2B SaaS environment where enablement is positioned as a strategic business function.

• Role based in Canada, with the opportunity to contribute to a globally oriented GTM organization.

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