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Squarespace · 2 weeks ago

Sales & Customer Success Enablement Manager

New York, NY

Full-time

Onsite

Senior Level

$154K/yr - $249K/yr

5+ years exp

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online, and they are seeking a Sales & Customer Success Enablement Manager to empower their B2B Sales and Customer Success teams. The role involves designing and delivering training programs, acting as a strategic partner to GTM teams, and measuring the impact of enablement initiatives.

Developer ToolsE-Commerce PlatformsPublishingSoftwareWeb Design

Comp. & Benefits

Responsibilities

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

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

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

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

Qualification

Sales EnablementCustomer Success EnablementInstructional DesignFacilitation SkillsB2B SaaS ExperienceTraining Program DevelopmentLearning Tools ProficiencyCommunication SkillsEmpathy for CustomersBuilder MindsetPerformance Data Analysis

Required

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

Experience supporting agency partners, channel sales, or partner ecosystems with scalable enablement programs