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

🧰 YOUR CRAFT (Job Duties & 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 all parts of the business to ensure strong execution, measurement, and impact visibility by aligning enablement initiatives to OKRs, 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 OKRs, 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, including 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

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 embedding AI and automation into everyday workflows.

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.

⚙️ YOUR FOUNDATION (Experience & Skills)

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

Strong cross-functional GTM expertise with deep understanding of the intersections between Product, Marketing, Sales, Customer Success, Support, and Business Operations.

Strategic and operational leader who aligns enablement initiatives with measurable revenue and lifecycle outcomes while building scalable systems and processes.

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.

Don’t let this list stop you from applying - If you are interested in the role, we’d love to hear from you!

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A few things to know about our hiring process: We are committed to making hiring at SQUIRE fair, thoughtful, and accessible for every candidate. Below are a few important details about our hiring practices and policies.

⚖️ Equal Employment Opportunity (EEO) SQUIRE is an equal opportunity employer committed to providing equal employment opportunities to all applicants without discrimination or harassment based on any characteristic protected by applicable law.

🤝 Interview Accommodations SQUIRE is committed to providing reasonable accommodations to individuals with disabilities throughout the hiring process. If you need an accommodation, please contact recruiting@getsquire.com .

🤖 AI in the Hiring Process SQUIRE may use AI tools to support application reviews, resume analysis, and other parts of the hiring process. These tools assist our recruiting team, but all final hiring decisions are made by humans. If you would like more information about how your data is processed, please contact recruiting@getsquire.com .

🛡️ E-Verify & Pre-Employment Screening SQUIRE participates in E-Verify. Employment offers may be contingent upon successful completion of applicable pre-employment screening, including background checks, in accordance with applicable law.

📋 Additional Resources & Legal Notices

Know Your Rights: Workplace Discrimination is Illegal (EEOC)

California Applicant Privacy Notice

Pay Transparency Nondiscrimination Provision

E-Verify Participation & Right to Work Posters

Pre-Employment Screening Information