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At Squarespace, Customer Operations empowers users to give voice to their ideas and make it easy for them when they need help. Our team runs 24/7 with about 400 people between New York, Dublin and a remote workforce. Customer Success Specialists work with our customers every day through email and live chat support interactions to ensure that they are achieving success with our platform and reaching their desired goals.

We are looking for a seasoned leader that is passionate and knowledgeable about all aspects of running an online business in the SMB space. The Manager of Customer Success will play a pivotal role in creating a results-driven framework that shifts ideologies from reactive to proactive. In this role, you will be responsible for developing and executing cross-sell and upsell tactics, increasing product engagement and usage of product add-ons and services, and ensuring customer satisfaction and retention for existing customers remains high. In addition to this, you will monitor the effectiveness of the greater Customer Success team and support Team Leads in forming a high performance team culture. 

You will report to the Director of Customer Support. 


  • Manage and oversee the operations for a team of Customer Success Team Leads and Specialists. Provide coaching, motivation, support, and expertise to help teams achieve their key performance targets.
  • Optimize the customer experience by shifting the team’s approach from a reactive support operation to a proactive results-driven mindset.
  • Segment the customer base to identify opportunities for upselling and cross-selling based on customer needs and behavior.
  • Facilitate relationships with Marketing, Help Center and Analytics teams to accurately size new opportunities and identify prospects and implement new initiatives. 
  • Implement strategies to drive revenue by increasing sales of product add-ons and product engagement to existing customers.
  • Partner with Customer Operations Analytics to build robust KPIs to attribute conversions and product adoption to Customer Success Specialists’ performance. 
  • Prepare reports for Senior Leadership and Finance to demonstrate measurable results with incremental ROI, product adoption rates, and customer satisfaction scores.
  • Create and manage a new results-based incentive plan to reward specialists for their impact.
  • Refine the customer contact flow and proactive outreach to create meaningful customer interactions.
  • Explore sales engines and Customer Relationship Management tools that map trends, report statistics, and make predictions for specialists. 


  • 5+ years of people leadership experience including managing managers and driving results through team performance
  • 3+ years of Customer Success experience, ideally in early stage growth companies
  • Experience increasing engagement and retention for small and medium sized businesses
  • Ability to articulate how technology solutions can improve the effectiveness of the Customer Success team
  • Expert communication skills and the ability to lead conversations that drive business for both parties and move the relationship forward.
  • Proven ability to develop strategies, translate them into initiatives and track successful delivery
  • Demonstrated operational excellence in analytical thinking, process development and improvement, problem solving, communication, delegation and planning

Benefits & Perks

  • A choice between medical plans with an option for 100% covered premiums
  • Health Savings Account with Squarespace funding
  • Fertility and adoption benefits
  • Supplemental Insurance plans
  • Headspace mindfulness app subscription
  • Retirement benefits with employer match
  • Flexible paid time off
  • Up to 20 weeks of paid family leave
  • Equity plan for all employees
  • $100 per month remote Stipend
  • Access to supplemental insurance plans for additional coverage
  • Education reimbursement
  • Employee donation match to community organizations
  • 6 Global Employee Resource Groups (ERGs)

Cash Compensation Range: $102,000 - $173,500 USD

The base salary for this position will vary based on job-related criteria including relevant skills, qualifications, 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), all Squarespace employees are eligible to receive equity in the company as part of their total compensation.

About Squarespace

Squarespace (NYSE: SQSP) 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, creating and managing social media presence with Bio Sites and Unfold, and hospitality business management via Tock. Our team of more than 1,700 is headquartered in bustling New York City, with offices in Chicago, Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and Australia. For more information about our company culture, visit

Our Commitment

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 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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