Head of GTM Enablement & Revenue Acceleration - Remote

SQUIRE; United States; Remote; USD 165,000 - 185,000; Full time

Job summary

SQUIRE is seeking a Director of GTM Enablement to design and lead a centralized enablement function, driving revenue impact and consistent execution across the customer lifecycle. You will oversee onboarding, product readiness, coaching, and AI-powered productivity systems—building scalable, data-driven programs with measurable outcomes.

Reporting to the Chief Business Operations Officer, this hands-on leader will manage a team of Enablement Managers, align initiatives to OKRs, and drive

Qualifications

• 10+ years of proven experience scaling GTM Enablement teams in high-growth SaaS environments.
• Experience in an SMB marketplace is a plus.
• Full-stack enablement experience across Sales, Product, Customer Success, and/or Support preferred.
• Demonstrated success in 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 and automation to modernize training, coaching, and workflow systems.

Responsibilities

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

Skills

GTM Enablement leadership

SaaS sales enablement

Cross-functional collaboration

AI-enabled training

Tools

Gong

ChatGPT

Claude

Job description

SQUIRE is seeking a Director of GTM Enablement to design and lead a centralized enablement function, driving revenue impact and consistent execution across the customer lifecycle. You will oversee onboarding, product readiness, coaching, and AI-powered productivity systems—building scalable, data-driven programs with measurable outcomes.

Reporting to the Chief Business Operations Officer, this hands-on leader will manage a team of Enablement Managers, align initiatives to OKRs, and drive