We're looking for a Systems Technologist to shape how AI is woven into our customer support operation. This is a hands-on, systems-minded role at the center of how Customer Operations functions: integrating external tools and internal platforms, building workflow automation, and enabling self-help. LLM-driven tools, agents, and automations are providing new and powerful opportunities to reshape all of these functions, and you'll be empowered as a technologist with more tools at your disposal than ever before. While we work closely with dedicated core product and engineering teams, we need someone who sits directly within Operations to move fast. You won't be building our core SaaS product; instead, you'll own the AI logic, the custom tools, and the integrations that empower our support agents and improve our customer experience, from the chatbot that talks to customers to the internal automations that take work off our agents' plates. If you're excited about putting LLMs into production, thinking end to end about how systems fit together, and seeing the immediate impact of your work on daily operations, this is the role for you. You'll Get To... Tooling & Custom Development Build and maintain custom Zendesk Apps for agent-facing data visibility Own the technical configuration of our AI chatbot (Assembled): API scripting, JSON parsing, conversation flow design Administer Custom Objects, Liquid Markup, and Dynamic Content Use AI coding tools to ship production code faster, with sound judgment on when generated code is ready Build quality checks and fallback paths so chatbot logic fails safely, not silently Integrations & Automation Connect our support tools to internal systems (Slack, Jira) and third-party vendors, using scripting and low-code platforms Ensure data flows correctly between our support frontend and backend services Own what you ship: build maintainable, well-tested solutions, and define how you'll know it's working in production Strategic Collaboration Translate Customer Operations needs into technical requirements and API specs for partner engineering teams Decide when a solution stays in Support Platform scope versus needs a scalable infrastructure project Who we're looking for... AI / LLM Integration: Experience building or configuring AI-powered features in production, chatbot logic, LLM API integrations, prompt design, and orchestration (Assembled, Ada, Ultimate.ai, or similar) AI-Assisted Development: Fluent with modern AI coding tools, with the judgment to know when generated code is production-ready API Fluency: Strong grasp of REST APIs, Webhooks, and JSON, including OAuth/API key auth Support Ecosystem Experience: Administering or developing for Zendesk (Zendesk Support, Guide, and App Framework) is highly preferred. Chatbot/AI Logic: Configuring chatbot logic and API integrations within chat flows (Assembled, Ada, Ultimate.ai, or similar) Low-Code Familiarity: Comfortable using Zapier, Make, or Workato when custom code isn't necessary. End-to-End Ownership: Track record of taking ambiguous problems to shipped, reliable solutions with minimal oversight Nice to Haves Liquid Markup Experience writing PRDs or technical specs Frontend knowledge (HTML/CSS) for internal tooling Production JavaScript (Node.js) and/or Python, building tools others depend on, not just scripting Benefits & Perks Health insurance with 100% covered premiums for you, your spouse or partner and your dependent children including medical, dental, and vision Life and Income Protection Fertility and adoption benefits Headspace mindfulness app subscription Global Employee Assistance Program Pension benefits with employer match Flexible paid time off 26 weeks paid maternity leave & 12 weeks paid paternity leave 2 weeks paid family care leave Annual Tax-Free Stipend Education reimbursement Employee donation match to community organizations 7 Global Employee Resource Groups (ERGs) Free lunch and snacks Close proximity to cultural landmarks such as Dublin Castle and St. Patrick's Cathedral Cash Compensation Range: €56,500 - €86,900 EUR 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 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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers. 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