IT Systems Administrator

At Lovingly, we're pioneering an AI-first approach to transform the gifting experience into something extraordinary. 🎁 By leveraging cutting-edge AI technology with a commitment to meaningful moments, we're redefining how gifts—especially floral gifts—are personalized, optimized, and shared. Our AI-powered platform connects a network of over 1,500 talented local florists, ensuring every gift delivers the data-driven personalization and emotional intelligence that our customers value. ✨

Our mission is to set a new standard in gifting through innovative AI technology, making each gesture meaningful, personal, and effortlessly delivered. 🚀 While Lovingly embraces a hybrid work model for many roles, this is a full-time, on-site position at our Hopewell Junction, NY headquarters. You'll be embedded in the heart of our AI operations, working hands-on with intelligent systems, predictive infrastructure, and a team committed to AI-enhanced excellence.

👩‍💻 Who you are

• 🧠 An AI-empowered IT expert who thrives in dynamic, technology-forward environments. You don't just maintain systems—you leverage AI to anticipate issues, automate solutions, and continuously optimize performance.
• 💡 Passionate about implementing AI-driven approaches to managing IT systems and infrastructure, seeing AI as a strategic partner rather than just another tool.
• 📊 A leader in using predictive analytics and machine learning models to transform IT operations from reactive to proactive, preventing issues before they impact business.
• ⚙️ Skilled at leveraging AI tools like ChatGPT, Claude, and custom LLMs to script advanced solutions, automate routine troubleshooting, and enhance security protocols.
• 📈 Driven by data-backed decisions, continuously experimenting with AI implementations that deliver measurable improvements to system reliability and efficiency.
• 🤝 An advocate for ethical AI deployment, ensuring that automation enhances human capabilities rather than replacing them.

This role isn't for those comfortable with traditional, manual IT approaches. It's for innovators ready to embrace AI as a force-multiplier that transforms what a single administrator can accomplish. ⚡

🔧 What you'll do

In this AI-first position, you'll use intelligent automation to accomplish the work of an entire team. Key responsibilities include:

• 🤖 AI-Powered Automation: Design and implement next-generation solutions using LLMs, ChatGPT, Claude, PowerShell scripting, and Power Automate to create self-healing systems and predictive maintenance workflows.
• ☁️ Intelligent Microsoft 365 Administration: Deploy AI tools to manage and optimize Entra, Intune, Exchange, and SharePoint, implementing machine learning for anomaly detection and security enhancement.
• 🌐 AI-Enhanced Network Management: Leverage predictive analytics to optimize network performance across multiple locations, using AI to identify potential bottlenecks before they impact operations.
• 🔒 Zero-Trust Security with AI: Implement advanced AI-powered security systems that continuously learn from threats, automatically adjust security postures, and provide real-time vulnerability management.
• 📱 Smart Device and Application Lifecycle: Deploy AI models to predict hardware failures, optimize application performance, and automate resource allocation for critical systems like Salesforce and Zendesk.
• 🔍 AI-Augmented Troubleshooting: Utilize custom-trained AI models to diagnose complex issues, recommend solutions, and build an ever-improving knowledge base that enhances company-wide technical resilience.
• 🏗️ Physical Infrastructure Optimization: Apply IoT sensors and AI analytics to maintain optimal conditions for physical systems, predicting maintenance needs before failures occur.

If you're not excited about pioneering AI applications in systems administration, transforming traditional IT into an intelligent, largely self-maintaining environment, this role isn't for you. 🚫

Requirements

We're looking for an AI-first professional with:

• 🕒 At least 7 years of progressive, hands-on experience in IT systems administration, with demonstrated success in implementing AI solutions in mixed Windows and Mac environments.
• 🔝 Advanced expertise in:
• Using AI tools (ChatGPT, Claude, custom LLMs) for IT automation and problem-solving
• Microsoft 365 administration with AI-enhanced management
• AI-powered network monitoring and security optimization, particularly with Ubiquiti equipment
• Cloud platforms like Azure, with experience in machine learning operations (MLOps)
• 💻 Proficiency in:
• Building and deploying AI-enhanced automation scripts (PowerShell and Python)
• Creating custom GPTs or AI agents for specific IT management functions
• Implementing predictive analytics for system performance and security
• ⚡ Demonstrated success in high-pressure environments where AI-driven uptime prediction and intelligent security are non-negotiable.
• 🏆 Certifications including:
• Microsoft 365 Certified: Enterprise Administrator Expert
• Networking certification (e.g., CCNA)
• AI/ML certification (preferred)
• ✅ Preferred qualifications include experience with:
• Production AI/ML implementations in IT operations
• AI-enhanced e-commerce platforms
• ITIL processes optimized through artificial intelligence

Benefits

💰 Salary Range

• This position offers a salary between $76,000 and $90,000 per annum, based on AI expertise, technical experience, and background.

🎁 Benefits

• 🏖️ 22 days PTO—use them however you want!
• 🎉 12 paid holidays
• 🏥 Comprehensive benefits, including health, dental, and vision
• 💸 401k with guaranteed 3% salary contribution
• 🧠 AI learning and certification stipend
• 🛠️ Access to premium AI tools and platforms for professional development
• 📚 Ongoing development opportunities, plus a 25% tuition discount at Marist College (including online AI programs)