Define and lead the strategy, operating model, and evolution of SQUIRE’s centralized enablement function
Lead a team of Enablement Managers and serve as a strategic advisor to executive leadership
Own onboarding, product and launch readiness, skills development, coaching frameworks, communications, knowledge management, and AI-powered productivity systems
Define and own KPIs tied to quota attainment, ramp time, win rates, product adoption, lifecycle expansion, and execution consistency

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

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

Director, GTM Enablement

Key skills