Director, GTM Enablement

SQUIRE

3d•$165,000 - $185,000•Remote

About The Position

The Director of GTM Enablement defines and leads the vision, strategy, operating model, and evolution of SQUIRE’s centralized enablement function. This leader builds a scalable, data-driven organization that drives measurable revenue impact and consistent execution across the full customer lifecycle. The role leads a team of Enablement Managers and advises department leadership, connecting company strategy to frontline execution. The Director oversees employee onboarding, product and launch readiness, ongoing skills development, coaching, communications, knowledge management, and AI-powered productivity systems. They are accountable for the effectiveness and continuous improvement of enablement initiatives against agreed-upon goals. This is a hands-on, player-coach role that combines strategic direction, scalable system-building, and organization-wide adoption. Success is measured against company OKRs and business outcomes such as quota attainment, ramp time, win rates, product adoption, and lifecycle expansion. The position reports to the Chief Business Operations Officer and is US-based remote.

Requirements

10+ years of proven experience scaling GTM Enablement teams in high-growth SaaS environments.
Demonstrated success building data-driven enablement programs in high-growth environments.
Experience operating in startup or scale-up environments where strategic ownership and hands-on execution coexist.
Proven experience leveraging AI tools and automation to modernize training, coaching, and workflow systems.
Strong cross-functional GTM expertise and deep understanding of the intersections between Product, Marketing, Sales, Customer Success, Support, and Business Operations.
Ability to align enablement initiatives with measurable revenue and lifecycle outcomes while building scalable systems and processes.
Strong communication skills and ability to build consensus across senior leadership and diverse teams.
Accountable and empathetic leadership, with a commitment to team growth, a culture of excellence, and continuous improvement.

Nice To Haves

Experience in an SMB marketplace.
Full-stack enablement experience across Sales, Product, Customer Success, and/or Support.
Experience with AI tools such as ChatGPT, Claude, and Gong.

Responsibilities

Build expertise in SQUIRE’s GTM strategy, industry, buyer personas, and competitive landscape to develop enablement that improves frontline performance.
Partner across the business to align enablement initiatives with OKRs, revenue goals, lifecycle metrics, and measurable impact.
Own the long-term vision and roadmap for GTM Enablement, prioritizing and resourcing work against high-impact growth opportunities.
Define and track enablement success metrics tied to OKRs, revenue, and lifecycle outcomes, and drive organizational alignment and consistent execution.
Develop a shared product and feature launch-readiness framework for GTM teams.
Ensure teams are informed, confident, and equipped to bring new solutions to customers.
Build and scale enablement frameworks—including playbooks, discovery methods, objection handling, messaging, cadences, and knowledge systems—and empower Enablement Managers to execute and improve them.
Define onboarding and coaching standards and models that reduce ramp time, accelerate productivity, and equip frontline leaders to drive accountability and performance.
Lead high-impact enablement and reinforcement programs, such as Sales Kickoff and quarterly trainings, aligned with strategic priorities and revenue goals to drive lasting behavior change.
Set standards for product, technical, and communication readiness across Support and post-sale teams to ensure consistent messaging and a seamless customer experience.
Build frontline feedback loops that inform training priorities, surface product insights, and support continuous lifecycle improvement.
Own the AI and emerging technology strategy for Enablement, using tools to personalize learning, analyze calls, and generate content to improve productivity and performance.
Modernize SQUIRE’s knowledge and enablement ecosystem so information is accurate, searchable, and continuously updated, embedding AI and automation into everyday workflows.
Lead and develop a team of Enablement Managers and advise department leadership.