Director, GTM Enablement

The Director of GTM Enablement defines and leads the vision, strategy, operating model, and evolution of SQUIRE’s centralized enablement function. By building a scalable, data-driven organization, this leader drives measurable revenue impact and consistent execution across the full customer lifecycle.

This role leads a team of Enablement Managers and serves as a strategic advisor to department leadership, connecting company strategy to frontline execution. They oversee employee onboardings, product and launch readiness, ongoing skills development, coaching, communications, knowledge management, and AI-powered productivity systems. This leader will be accountable for the effectiveness and continuous improvement of enablement initiatives against agreed-upon goals

While strategic in scope, this is a hands-on, player-coach role requiring someone who can set direction, build scalable systems, and drive adoption across the organization. Success is measured by business outcomes aligned with company OKRs, including quota attainment, ramp time, win rates, product adoption, and lifecycle expansion.

Reports To: Chief Business Operations Officer

Location: US
- Remote

Type: Full-time

Compensation Range: $165,000 - $185,000 base salary + 15% bonus

• Build deep expertise in SQUIRE’s GTM strategy, industry, buyer personas, and competitive landscape to create enablement that drives frontline performance.

• Partner with all parts of the business to ensure strong execution, measurement, and impact visibility by aligning enablement initiatives to OKRs, revenue goals and lifecycle metrics

• Own the long-term vision and roadmap for GTM Enablement

• Ensure work is prioritized and resourced against the highest-impact growth opportunities.

• Define and track clear success metrics for Enablement by tying initiatives to OKRs, revenue, and lifecycle outcomes while driving alignment and consistent execution across the organization.

• Develop a consistent and shared framework for product and feature launch readiness across GTM teams

• Ensure that teams are confident, informed, and equipped to bring new solutions to our customers

• Build and scale strategic enablement frameworks that drive measurable results and empower Enablement Managers to execute and continuously improve, including playbooks, discovery methods, objection handling, messaging, cadences, and knowledge systems

• Define the onboarding and coaching model by setting clear standards that reduce ramp time, accelerate productivity, and equip frontline leaders with practical frameworks to drive accountability and performance.

• Lead high-impact enablement moments and reinforcement programs (e.g., Sales Kickoff, quarterly trainings) by ensuring they align to strategic priorities and revenue goals that drive lasting behavior change, not just knowledge transfer.

• Set clear standards for product, technical, and communication readiness across Support and post-sale teams to ensure consistent messaging and a seamless customer experience.

• Build structured frontline feedback loops that inform training priorities, surface product insights, and drive continuous lifecycle improvement.

• Own the AI and emerging technology strategy for Enablement by leveraging tools to personalize learning, analyze calls, and generate content to drive measurable gains in productivity and performance.

• Modernize SQUIRE’s knowledge and enablement ecosystem by ensuring information is accurate, searchable, and continuously updated while…