AI and Automation Lead (Remote)

Squarespace is seeking a high-impact AI & Automation Lead to join our Customer Operations department. As our primary AI program owner and subject matter expert, this role will be instrumental in defining how AI will transform how we serve our customers and empower our frontline teams. In this pivotal individual contributor role, you will define the future of AI within our customer operations, from crafting the roadmap and leading complex implementations to ensuring ethical deployment and measurable impact on the customer journey.

This role reports to the Director of Strategy & Optimization on the Customer Operations team, based remotely.

You'll Get To...

Program Strategy & Vision

• Work with SLT to define and own the roadmap for AI & Automation within Customer Operations.
• Identify and prioritize high-impact automation opportunities across the customer journey.
• Partner with stakeholders to align AI initiatives with broader business goals.

Cross-Functional Leadership

• Act as the primary liaison with Product, Engineering, Data Science, Legal, Security, and vendors on CustOps AI/Automation matters.
• Facilitate alignment across teams to ensure AI tools are designed for real-world operational needs.
• Upskilling contributors from other teams regarding AI tools and features, keeping teams informed about the current state of the industry and technology.

Implementation & Delivery

• Ensure delivery of AI and automation projects (e.g., chatbots, AI-driven triage & case routing, Agent-facing AI tools).
• Manage pilots, rollouts, change management, and feedback loops.
• Ensure adoption and usability of tools by frontline teams.

Data, Measurement, & Optimization

• Define KPIs for automation (e.g., deflection rate, handle time reduction, accuracy, CSAT impact).
• Continuously track performance, identify gaps, and iterate on solutions.
• Work with COA to facilitate reporting dashboards and regular updates for leadership.

Governance & Ethics

• Work with GRC to ensure responsible AI use: monitor for bias, ensure transparency, and comply with data privacy regulations.
• Develop processes for human-in-the-loop systems where needed.

Training & Change Management

• Collaborate with enablement teams to train staff on new tools.
• Foster a culture of innovation and adoption within the support organization.

Who We're Looking For...

• At least five years of experience in program or project leadership, ideally within customer support or operations
• 3-5 years of direct experience focused on AI/ML-driven products or initiatives, specifically within a customer-facing or support context
• Degree or certification specific to AI or an AI-related field; track record of seeking to expand skills and knowledge in the AI field, specifically directed toward support.
• Strong understanding of AI/ML tools and service automation technologies
• Experience in identifying strategic opportunities for AI to improve customer experience, operational efficiency, and agent effectiveness in a support setting
• Familiarity with tools like Zendesk, Salesforce, and generative AI platforms
• Excellent stakeholder management and communication skills
• Strong analytical skills to interpret support data (e.g., ticket volumes, resolution times, customer feedback) and identify areas where AI can drive significant improvements.
• Understanding of data governance & privacy: Awareness of the importance of data quality, data privacy (e.g., GDPR, CCPA), and ethical data use in AI applications for support.

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
• 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
• $100 per month remote Stipend
• Access to supplemental insurance plans for additional coverage
• Education reimbursement
• Employee donation match to community organizations
• 8 Global Employee Resource Groups (ERGs)

Cash Compensation Range: $115,500 - $203,550 USD

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.

About Squarespace

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.

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.

#LI-Remote