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The all-in-one platform to power your Barbershop Operations
The Role
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. 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.
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)
- 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
- 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
- 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
- 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
- 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
- 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
Strategy & Revenue Alignment
Centralized Enablement Strategy, Governance & Roadmap
Product & Launch Readiness
Onboarding, Training & Coaching Infrastructure
Support Enablement & Customer Experience Alignment
AI, Knowledge Management & Emerging Technology
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)
- 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
Experience
Leadership & Capabilities
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] and someone on our team will respond to your request.
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.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.
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. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.
E-Verify Participation
SQUIRE participates in E-Verify. Learn more about E-verify here.
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The Company
What We Do
SQUIRE is the world’s leading and fastest-growing software technology platform for barbershops, a hundred-billion-dollar global industry. We provide a one-stop solution that helps small business entrepreneurs run and grow their businesses. SQUIRE is also the premiere booking engine that connects people with great barbers nationwide. We make it easy to discover and book the best barbers wherever you are, in just a few taps. With headquarters in New York and a presence in major cities in the United States, U.K. and Canada, SQUIRE is the market leader in technology solutions for the barbershop industry. SQUIRE is a Series D company and has raised over $165M to date. For more information, please visit getSquire.com or download the SQUIRE app from the App or Play Store.
Why Work With Us
We're not just another start-up; we're a community of innovators, drivers, and achievers driven by our mission - to elevate, celebrate and empower the barbering community. Check out our Culture Book to learn more - https://handbooks.getsquire.com/recruiting.
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