Squarespace

Compensation

Full Description

About the position Responsibilities • Build a World-Class Enablement Engine • Design and deliver onboarding programs for Sales and CS that combine live facilitation, e-learning, and on-the-job application—helping new hires ramp quickly and effectively. • Take full ownership of early ramp success, ensuring new team members hit the ground running with confidence and clarity. • Create scalable playbooks, talk tracks, certification programs, and enablement assets that evolve alongside our product roadmap and GTM strategy. • Leverage adult learning principles and instructional design best practices to develop engaging, learner-centered training experiences. • Deliver live facilitation of workshops, certifications, and enablement sessions for Sales and CS teams across multiple segments. • Act as a Strategic Partner to GTM Teams • Partner with Sales and CS leaders to identify skill gaps, process friction, and knowledge needs, then design targeted enablement solutions. • Serve as a trusted advisor to GTM leadership by surfacing insights from the field and translating them into actionable content and programs. • Ensure Sales and CS teams are armed with the latest competitive intelligence, product positioning, and customer insights. • Embed within team rhythms (pipeline reviews, QBRs, customer journey workshops) to stay connected to performance and evolving challenges. • Measure & Iterate Enablement Impact • Define and track enablement KPIs, such as time-to-ramp, attainment, and program adoption, and tie them directly to pipeline health, revenue productivity, and customer outcomes. • Use performance data and learner feedback to continuously optimize enablement strategy, delivery formats, and content effectiveness. • Partner with Sales Ops and Product Marketing to maintain a centralized enablement hub as the single source of truth. Requirements • 5+ years of experience in Sales Enablement, Customer Success Enablement, or related Learning & Development roles in high-growth, high-velocity B2B SaaS environments. • Proven success in designing and delivering onboarding, training, and enablement programs that measurably improve ramp time, productivity, and retention. • Strong expertise in facilitation and learning design, grounded in adult learning principles and proven instructional methodologies. • Exceptional communication and presentation skills; comfortable facilitating at all levels, from new hires to executives. • Proficiency with enablement and learning tools (CRM, LMS, and sales enablement platforms such as Salesforce, Gong, Highspot, Seismic, Salesloft, or Avarra). • A builder mindset—energized by ambiguity, skilled at creating clarity, and proven at designing scalable programs from the ground up. • Deep empathy for Sales, CS, and the customer journey, with the ability to translate frontline challenges into impactful enablement. Nice-to-haves • Experience supporting agency partners, channel sales, or partner ecosystems with scalable enablement programs. • Familiarity with the Squarespace platform, or other commerce and creative platform, is a strong plus. Benefits • A choice between medical plans with an option for 100% covered premiums • Fertility and adoption benefits • Access to supplemental insurance plans for additional coverage • Headspace mindfulness app subscription • Global Employee Assistance Program • Retirement benefits with employer match • Flexible paid time off • 12 weeks paid parental leave and family care leave • Pretax commuter benefit • Education reimbursement • Employee donation match to community organizations • 8 Global Employee Resource Groups (ERGs) • Dog-friendly workplace • Free lunch and snacks • Private rooftop • Hack week twice per year