AI and Automation Lead
@ Squarespace

Hybrid
$159,525
Hybrid
Full Time
Posted 18 hours ago

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XXXXXXXX XXXXXXXXXXXXX XXXXXXXXXX***** @squarespace.com
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Job Details

Overview

Squarespace is seeking a high-impact AI and Automation Lead to join our Customer Operations department. In this pivotal individual contributor role, you will define the future of AI within customer operations by crafting the roadmap, leading complex implementations, and ensuring ethical deployment with measurable impact on the customer journey.

Program Strategy & Vision

Work with the Senior Leadership Team to define and own the roadmap for AI and Automation. Identify and prioritize high-impact automation opportunities and align initiatives with broader business goals.

Cross-Functional Leadership

Act as the primary liaison with Product, Engineering, Data Science, Legal, Security, and vendors. Facilitate cross-team alignment and upskill contributors on the latest AI tools and industry trends.

Implementation & Delivery

Manage pilots, rollouts, change management, and feedback for AI projects such as chatbots and AI-driven triage. Ensure the adoption and usability of these tools by frontline teams.

Data, Measurement & Optimization

Define KPIs like deflection rate and handle time reduction. Continuously track performance, identify gaps, and iterate on solutions in collaboration with the reporting team.

Governance & Ethics

Collaborate with GRC to ensure responsible AI use by monitoring bias, maintaining transparency, and ensuring data privacy. Develop processes for human-in-the-loop systems where necessary.

Training & Change Management

Work with enablement teams to train staff on new tools and foster a culture of innovation within the support organization.

Qualifications

- At least five years of experience in program or project leadership, ideally within customer support or operations. - 3-5 years of direct AI/ML-driven product experience in a customer-facing context. - Degree or certification in an AI-related field. - Strong understanding of AI/ML tools, automation technologies, and data governance. - Excellent stakeholder management, communication, and analytical skills.

Benefits & Perks

Includes competitive medical plans, HSA funding, fertility and adoption benefits, flexible paid time off, parental leave, a remote stipend, education reimbursement, and more.

About Squarespace

Squarespace is a design-driven platform that supports entrepreneurs in building brands and businesses online. With over 1,500 employees globally and headquarters in New York City, Squarespace empowers millions worldwide.

Key skills/competency

AI, Automation, Strategy, Customer Operations, Implementation, Leadership, Data Analysis, Governance, Training, Change Management

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How to Get Hired at Squarespace

🎯 Tips for Getting Hired

  • Tailor resume: Highlight AI and automation experience.
  • Customize cover letter: Emphasize customer operations expertise.
  • Research Squarespace: Understand its culture and products.
  • Prepare for interviews: Practice discussing cross-functional leadership.

📝 Interview Preparation Advice

Technical Preparation

Review AI/ML implementation case studies.
Practice using automation tools like Zendesk and Salesforce.
Refine skills in data analysis and KPI measurement.
Study AI ethics and compliance requirements.

Behavioral Questions

Describe a challenging project coordination experience.
Explain your stakeholder communication style.
Discuss a time you led change management.
Share how you resolved team conflicts.

Frequently Asked Questions