Squarespace is seeking a Sales & Customer Success Enablement Manager to design, launch, & scale a new function dedicated to empowering our B2B Sales & Customer Success teams. Your mission: help our GTM teams deliver best-in-class customer experiences while driving revenue, retention, & 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, & accelerate our revenue-facing teams. Were looking for a strategic enablement leader who combines facilitation & instructional design expertise with commercial acumensomeone who thrives at both leading workshops for senior GTM professionals & building scalable onboarding & training programs in a fast-paced, high-growth environment.

You'll Get To...

Build a World-Class Enablement Engine

• Design & deliver onboarding programs for Sales & CS that combine live facilitation, e-learning, & on-the-job applicationhelping new hires ramp quickly & effectively. Take full ownership of early ramp success, ensuring new team members hit the ground running with confidence & clarity.
• Create scalable playbooks, talk tracks, certification programs, & enablement assets that evolve alongside our product roadmap & GTM strategy.
• Leverage adult learning principles & instructional design best practices to develop engaging, learner-centered training experiences.
• Deliver live facilitation of workshops, certifications, & enablement sessions for Sales & CS teams across multiple segments.

Act as a Strategic Partner to GTM Teams

• Partner with Sales & CS leaders to identify skill gaps, process friction, & knowledge needs, then design targeted enablement solutions.
• Serve as a trusted advisor to GTM leadership by surfacing insights from the field & translating them into actionable content & programs.
• Ensure Sales & CS teams are armed with the latest competitive intelligence, product positioning, & customer insights.
• Embed within team rhythms (pipeline reviews, QBRs, customer journey workshops) to stay connected to performance & evolving challenges.

Measure & Iterate Enablement Impact

• Define & track enablement KPIs, such as time-to-ramp, attainment, & program adoption, & tie them directly to pipeline health, revenue productivity, & customer outcomes.
• Use performance data & learner feedback to continuously optimize enablement strategy, delivery formats, & content effectiveness.
• Partner with Sales Ops & Product Marketing to maintain a centralized enablement hub as the single source of truth.
  
  

Who Were 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 & delivering onboarding, training, & enablement programs that measurably improve ramp time, productivity, & retention.
• Strong expertise in facilitation & learning design, grounded in adult learning principles & proven instructional methodologies.
• Exceptional communication & presentation skills; comfortable facilitating at all levels, from new hires to executives.
• Proficiency with enablement & learning tools (CRM, LMS, & sales enablement platforms such as Salesforce, Gong, Highspot, Seismic, Salesloft, or Avarra).
• A builder mindsetenergized by ambiguity, skilled at creating clarity, & proven at designing scalable programs from the ground up.
• Deep empathy for Sales, CS, & 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 & creative platform, is a strong plus.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility & 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
• 20 weeks for parental leave & up to 12 weeks to care for an ill family member
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 8 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $125,000 - $201,250 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, & location, among other factors. 

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Our Commitment 

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & celebrate the diversity of our customer base, but we also strive for the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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