AI and Automation Lead

Summary

Join Squarespace as a high-impact AI & Automation Lead in the Customer Operations department. As the primary AI program owner, you will define how AI transforms customer service and empowers teams. This individual contributor role involves crafting the AI roadmap, leading complex implementations, ensuring ethical deployment, and measuring impact on the customer journey. You will work with various stakeholders, including SLT, Product, Engineering, and Data Science teams. The role requires strong program leadership, AI/ML expertise, and excellent communication skills. This remote position reports to the Director of Strategy & Optimization.

Requirements

• 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

Responsibilities

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

Benefits

• 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)