Team Lead, Customer Success

Squarespace is seeking a Customer Success Manager (CSM) Team Lead to launch and scale our Customer Success function from the ground up. This role is instrumental in shaping the early strategy and operations of a team that will engage directly with our most strategic, high-value users to improve retention, expand product adoption, and deliver measurable business outcomes. You’ll manage a team of CSMs, build scalable playbooks, and collaborate cross-functionally to define the future of CS at Squarespace.

This role reports to the VP of Sales and is based out of Squarespace's NYC Headquarters (hybrid).

Customer Success Strategy & Execution

• Design, launch and manage a Customer Success program focused on driving product adoption, retention, and account health for high-value customers. Key metrics of success include growing net recurring revenue and minimizing churn. 
• Create and implement success plans, outreach cadences, and key touchpoints across the customer journey, from onboarding to renewal
• Work with your team to define and monitor customer health signals and deliver proactive, value-based engagement
• Serve as a senior voice in building CS playbooks, QBR templates, risk mitigation tactics, and cross-team coordination flows

Team Leadership & Coaching

• Recruit, onboard, and mentor a team of Customer Success Managers (CSMs)
• Foster a high-performance culture focused on customer outcomes, operational rigor, and personal growth
• Set clear team KPIs and own weekly team rhythms, reporting, and internal updates
• Collaborate on account plans with Customer Success Managers to identify opportunities to increase customer value

Cross-Functional Collaboration

• Partner with Product, Support, Analytics, Sales, and Operations teams to centralize insights, surface risks, and improve lifecycle touchpoints
• Own the retention forecast of our strategic customers, reporting risks, and their mitigation statuses
• Help identify and prioritize data and tooling requirements to support long-term program scaling
• Represent the CS function in internal strategic conversations and senior leadership reviews

Operational Design & Measurement

• Help define health scoring models, success criteria, and reporting dashboards
• Identify repeatable systems and tools to scale engagement to future cohorts
• Track and report key pilot metrics (e.g. NRR, feature adoption, CSAT, retention)

• 6+ years in Customer Success or Account Management, SMB experience preferred
• 3+ years of experience managing customer-facing teams (CSMs, AMs)
• Experience launching or growing CS or AM programs from early-stage to maturity
• Strong understanding of customer lifecycle management, success planning, and churn prevention
• Proven ability to lead cross-functional initiatives with Product, Support, and RevOps
• Data- and outcomes-oriented: comfortable setting goals and measuring success through dashboards, CRM tools, and customer signals
• Comfortable working in ambiguity; capable of building structure from scratch
• Experience using CS tooling such as Gainsight, Catalyst, or Totango is a plus
• Familiarity with Squarespace product is a plus

• A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
• Supplemental Life and Disability Insurance plans
• Fertility and adoption benefits
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 20 weeks for parental leave and 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 and snacks
• Private rooftop
• Hack week twice per year

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and 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.

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

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward 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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