Director, GTM Enablement

SQUIRE

6h • $160,000 - $180,000 • Remote

About The Position

The Director of GTM Enablement defines and leads the 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 executional consistency across the full customer lifecycle.

This role leads a team of Enablement Managers and serves as a strategic advisor to executive leadership. They own onboarding, product and launch readiness, skills development, coaching frameworks, communications, knowledge management, and AI-powered productivity systems across the company — acting as the connective tissue between company strategy and field execution.

Success is measured by business outcomes. This leader defines and owns KPIs tied to quota attainment, ramp time, win rates, product adoption, lifecycle expansion, and execution consistency. While highly strategic in scope, this is a hands-on operator who can set direction, build scalable systems, and drive adoption across cross-functional stakeholders.

Requirements

• 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 (ChatGPT, Claude, Gong) and automation to modernize training, coaching, and workflow systems
• Enterprise-wide GTM acumen with deep understanding of the intersections between Product, Marketing, Sales, Customer Success, Support, and Revenue Operations
• Strategic and operational leader who connects enablement initiatives to measurable revenue and lifecycle outcomes—and builds scalable systems and governance from ambiguity
• Strong communication skills with the ability to build consensus across senior leadership and diverse teams
• Accountable and empathetic leader who invests in their team’s growth, fosters a culture of excellence, and champions continuous improvement

Responsibilities

• Strategy & Revenue Alignment
• Build deep expertise in SQUIRE’s GTM strategy, industry, buyer personas, and competitive landscape to create enablement that drives frontline performance
• Partner with RevOps and Strategy to ensure strong execution, measurement, and impact visibility by aligning enablement initiatives to revenue goals and lifecycle metrics
• Centralized Enablement Strategy, Governance & Roadmap
• 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 revenue and lifecycle outcomes while driving alignment and consistent execution across the organization
• Product & Launch Readiness
• 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 - This will include playbooks, discovery methods, objection handling, messaging, cadences, and knowledge systems
• Onboarding, Training & Coaching Infrastructure
• 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
• Support Enablement & Customer Experience Alignment
• 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
• AI, Knowledge Management & Emerging Technology
• Modernize SQUIRE’s knowledge and enablement ecosystem by ensuring information is accurate, searchable, and continuously updated while embedding AI and automation into everyday workflows
• 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

Benefits

• Base Salary ($160,000 - $180,000) + Bonus (15%)
• New hire stock grant
• 100% employer paid medical, dental, and vision insurance for you and your dependents
• 401K plan with company contribution
• Generous PTO and Parental Leave policies

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed