SQUIRE is the only management platform built exclusively for barbershop owners. Scheduling, payments, staff, and marketing - under one roof. Trusted by 5,000+ shops. Backed by Y Combinator, CRV and ICONIQ.
About the role
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 Found on 1752vc Careers, the job board for startup and VC roles.
What they're looking for
- 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
More about this role
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.
Type : Full-time
Strategy & Revenue Alignment
Build deep expertise in SQUIRE’s GTM strategy,...
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