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Sales & Customer Success Enablement Manager
About the position
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.
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
- 7 Global Employee Resource Groups (ERGs)
- Dog-friendly workplace
- Free lunch and snacks
- Private rooftop
- Hack week twice per year
