Sales & Customer Success Enablement Manager

Squarespace is seeking a Sales & Customer Success Enablement Manager to design, launch, and scale a new function dedicated to empowering our B2B Sales and Customer Success teams. Your mission: help our GTM teams deliver best-in-class customer experiences while driving revenue, retention, and growth.

This is a high-visibility, high-impact individual contributor role reporting to our Director of Sales & GTM Operations, with direct ownership over how we train, enable, and accelerate our revenue-facing teams. We're looking for a strategic enablement leader who combines facilitation and instructional design expertise with commercial acumen-someone who thrives at both leading workshops for senior GTM professionals and building scalable onboarding and training programs in a fast-paced, high-growth environment.

You'll Get To...

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.

Who We're Looking For

* 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. Familiarity with the Squarespace platform, or other commerce and creative platform, is a strong plus.

Benefits & Perks

* 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

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