SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.
Founded in 2015, SQUIRE is trusted by more than 30,000 barbers across 5,000+ shops in more than a thousand cities worldwide. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.
For more information, please visit getsquire.com or download the SQUIRE app from the App or Play Store.
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.
Reports To: VP, GTM Operations
Location: US - Remote
Type: Full Time
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
The duties and responsibilities outlined above are not a comprehensive list, and additional tasks may be assigned from time to time based on business needs.
Experience
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
Leadership & Capabilities
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
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Getsquire is a platform that connects small businesses and entrepreneurs with freelance service providers for tasks like bookkeeping, virtual assistance, and administrative support. It serves as a marketplace matching businesses with qualified professionals to handle back-office operations.
Visit website$160,000 – $180,000
Base + Bonus · Stock Options
