Job Description
WHO WE ARE
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.
ABOUT THE ROLE
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
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 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.
* 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.
* 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.
* 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.
YOUR FOUNDATION (Experience & Skills)
* Experience
10+ years of proven experience scaling GTM Enablement teams in high-growth SaaS environments. Full-stack enablement experience across Sales, Product, Customer Success, and/or Support preferred.
* Leadership & Capabilities
Enterprise-wide GTM acumen with a deep understanding of the intersections between Product, Marketing, Sales, Customer Success, Support, and Revenue Operations. Strong communication skills with the ability to build consensus across senior leadership and diverse teams.
WHAT WE OFFER
* 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
Interview Accommodations
SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to [email protected] .
EEO Provision
SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
Pay Transparency Nondiscrimination Provision
SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant.
E-Verify Participation
SQUIRE participates in E-Verify.
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