Automations Engineer, Post Sales Systems

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 JOB SUMMARY As a Support Automation Engineer on the Post Sales Systems team, you will design, build, and maintain the automation and AI systems that power ClickUp's post-sales support organization. You'll be responsible for translating business workflows in Zendesk and related CX platforms into scalable, intelligent automations that reduce manual effort, improve customer experience, and free up our support team to focus on high-value interactions. This role sits at the intersection of engineering rigor and customer empathy. You'll partner closely with the Support and Success organizations, GTM Systems Leadership, and cross-functional stakeholders to automate away toil, surface insights through AI, and build systems that adapt to how support teams actually work. The kind of person who thrives here moves fast, takes full ownership of what they build, and is genuinely excited about applying AI to real operational problems. This role is a direct contributor to GTMSOE's broader mission of operational excellence across the GTM org. KEY RESPONSIBILITIES AI-POWERED AUTOMATION DESIGN & DEVELOPMENT - Design and build automations in Zendesk that reduce repetitive support work: ticket routing, field population, note summarization, escalation logic, and customer outreach workflows. - Develop AI-driven workflows using Zendesk AI, custom LLM integrations, and ClickUp Super Agents to automate tasks like ticket summarization, sentiment analysis, knowledge base matching, and response suggestions. - Architect low-code/no-code automation solutions using Workato, Zapier, and similar integration platforms to connect Zendesk with Salesforce, ClickUp, Maven chatbot, and other tools. - Own the full lifecycle of an automation: discovery, design, build, testing, deployment, and ongoing optimization based on usage and feedback. CX SYSTEMS INTEGRATION & DATA FLOW - Ensure seamless data flow between Zendesk, Salesforce, ClickUp, Chili Piper, Maven AGI chatbot, and other tools in the support tech stack. - Design integration patterns that keep data clean, up-to-date, and accessible to downstream systems without creating maintenance nightmares. - Build and maintain reporting dashboards and data pipelines that surface support health, automation impact, and team productivity metrics. - Partner with the Support org to identify pain points, bottlenecks, and opportunities where AI and automation can deliver measurable value. AI CAPABILITY EXPANSION - Experiment with emerging AI/LLM capabilities (agents, RAG, fine-tuning) and determine which are production-ready for support workflows. - Build reusable AI templates and patterns that other CX Systems team members can leverage, promoting consistency and reducing duplication. - Collaborate with the broader GTM Systems Engineering team to share learnings and align on AI strategy across post-sales, sales, and finance domains. - Log AI/automation work in the team's AI Excellence registry to promote transparency and cross-team learning. RELIABILITY & CONTINUOUS IMPROVEMENT - Monitor automation health, error rates, and SLAs; proactively identify and resolve issues before they impact support operations. - Gather feedback from support teams and stakeholders; iterate on existing automations to improve accuracy, reduce false positives, and adapt to evolving business needs. - Maintain documentation and runbooks so that support and CX teams understand how automations work and when to escalate issues. - Help simplify and modernize existing architecture in Zendesk and connecting systems to improve long-term maintainability. CROSS-FUNCTIONAL COLLABORATION - Work closely with GTM Support teammates and leadership on intake, prioritization, and task execution. - Partner with the Support and Success organizations and key stakeholders to translate business requirements into technical specifications. - Contribute to the GTM Systems Engineering operating model: maintain task hygiene and communicate proactively on large initiatives. QUALIFICATIONS EXPERIENCE - 3–5+ years in systems administration, business systems engineering, or customer support platform work. - Demonstrated experience building automations or integrations that have shipped to production and delivered measurable business value. - Hands-on experience with CX platforms, particularly Zendesk at an admin level or higher. - Experience in a high-velocity, collaborative environment where you wear multiple hats and adapt quickly. - Optional but valued: experience with ClickUp, Maven/chatbots, GTM systems, or support-focused SaaS operations. SKILLS & COMPETENCIES Technical - Zendesk expertise: Hands-on experience with automations, triggers, business rules, and configuration (admin-level proficiency or higher). - Integration & API work: Comfortable with REST APIs, webhooks, and integration platforms (Retool, Workato, Zapier, or similar low-code tools). - AI & LLMs: Familiarity with prompt engineering, LLM APIs (OpenAI, Claude, etc.), MCP, and how to safely integrate AI into production workflows. You don't need to be an ML engineer, but you should understand when and how to apply AI to solve real problems. - Data & scripting: Comfortable working with JSON, SQL, or light scripting (Python, JavaScript) to build data pipelines and transform data between systems. - Salesforce integration: Understanding of Zendesk-to-Salesforce sync workflows, object relationships, and common integration patterns. Operational & Mindset - Ownership: You take full responsibility for the systems you build—reliability, documentation, and continuous improvement included. You don