IT Systems Administrator

Who we are 

 Lovingly pairs our passion for creating meaningful moments with cutting-edge technology to redefine how gifts—especially floral gifts—are sent today. We believe gifting should be intentional, personal, and deeply meaningful. 

Our mission is to set a new standard in gifting through innovative technology, ensuring that every gift is effortlessly delivered to those who matter most to you. With a network of over 1,500 talented local florists nationwide, we guarantee your gift will stand out. 

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 operations, working hands-on with systems, infrastructure, and a team committed to excellence. 

Who you are 

• A hands-on IT expert who thrives in dynamic, technical environments. You’re not just a strategist—you’re someone who rolls up their sleeves and gets to work solving complex issues in real time. 

• Passionate about managing and optimizing IT systems and infrastructure, not delegating these tasks to others. 

• Comfortable being the first call when something goes wrong—and taking ownership of critical systems. 

• Dive deep into technical troubleshooting, whether it’s configuring a VPN, scripting a solution in PowerShell, or managing security protocols. 

• A proactive problem-solver with a strong sense of accountability. You don’t wait for instructions; you anticipate issues, propose solutions, and make improvements happen. 

• Driven to learn and adapt quickly to new tools, technologies, and challenges. 
  

This role isn’t for those who prefer a high-level, purely strategic approach. It’s for someone who wants to get their hands dirty—every single day. 

What you’ll do 

 This isn’t a position where you’ll manage a team of others to do the work; you are the team that gets things done. Key responsibilities include: 

• AI Automation: Creating solutions with tools like Zapier, LLMs, PowerShell, and Power Automate to streamline workflows and improve efficiency. 

• Microsoft 365 Administration: Managing and optimizing systems like Entra, Intune, Exchange, and SharePoint, with a focus on scalability and security. 

• Network Infrastructure: Designing, maintaining, and troubleshooting networks across multiple locations, including Ubiquiti equipment and site-to-site VPNs. 

• Cloud and Security Systems: Managing Azure cloud environments, implementing zero-trust architectures, and ensuring compliance with security best practices. 

• Device and Application Management: Overseeing the lifecycle of all Windows and Apple computers/devices and ensuring business-critical applications (like Salesforce and Zendesk) perform optimally. 

• Hands-On Problem Solving: Jumping in to troubleshoot, resolve, and prevent technical issues across the organization. 

• Physical Infrastructure: Maintaining physical systems, including cabling, hardware, and access controls.
   

If you don’t enjoy taking a hands-on approach to these kinds of responsibilities, this role isn’t for you. 

Requirements

We’re looking for a seasoned professional with: 

• At least 7 years of progressive, hands-on experience in IT systems administration in a mixed windows and mac environment. 

• Advanced expertise in:  

• Microsoft 365 administration. 

• Networking and security, particularly with Ubiquiti equipment. 

• Cloud platforms like Azure. 

• Proficiency in automation and scripting (PowerShell and Python preferred). 

• Demonstrated success in high-pressure environments where uptime and security are non-negotiable. 

• Certifications including:  

• Microsoft 365 Certified: Enterprise Administrator Expert. 

• Networking certification (e.g., CCNA). 

Preferred qualifications include experience with AI/ML implementations, e-commerce platforms, and ITIL processes. 

Salary Range 

 This position offers a salary between $76,000 and $90,000 per annum, based on skills, experience, and background. 

Benefits

• 22 days PTO—use them however you want! 

• 12 paid holidays. 

• Comprehensive benefits, including health, dental, and vision. 

• 401k with a guaranteed 3% salary contribution. 

• Ongoing professional development, including a 25% tuition discount at Marist College (online programs included).
   

Equal Opportunity Statement 

 We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or veteran status.