Senior Systems Administrator

Job DetailsJob Location: Winter Park - Winter Park, FL 32789Position Type: Full TimeEducation Level: 4 Year DegreeSalary Range: $125,000.00 - $145,000.00 Salary

About Rifle Paper Co:

At Rifle Paper Co, we believe that details matter from the artwork on the page to the technology and systems that help bring our products to life. What began as hand-printed illustrations has grown into a lifestyle brand carried by retailers around the world. As we continue to grow, our technology infrastructure plays a critical role in supporting our teams, operations, and business.

About the Role:

We’re looking for a hands-on and proactive Senior Systems Administrator to lead and support our hybrid cloud and on-premises infrastructure. Reporting to technology leadership, this role will be responsible for ensuring the reliability, security, scalability, and performance of our technology environment while partnering closely with the business to drive operational excellence.

This position is ideal for an infrastructure leader who enjoys solving complex technical challenges, improving operational maturity, mentoring others, and building scalable, secure technology solutions that support a rapidly growing business.

We believe great work can happen in different places, so this roles offers flexibility in where you work. You can be based in either our Winter Park, Florida or New York, New York Office, or remotely if you reside in one of the following states: Michigan, Texas, North Carolina, South Carolina, Virginia, and Tennessee.

The anticipated salary range for this role is $125,000 to $145,000 annually. Final compensation offered will be determined based on factors such as relevant experience, qualifications, skills, and geographic location.

What You Will Do:

• Design, implement, administer, and support secure, scalable cloud and on-premises infrastructure.
• Manage and maintain AWS and Microsoft Azure environments, Windows Server infrastructure, and core networking components.
• Administer switches, routers, wireless infrastructure, VPNs, firewalls, storage, and endpoint management platforms.
• Support a hybrid Windows, macOS, iOS, and mobile device environment.
• Monitor system performance, reliability, capacity, availability, and security while proactively identifying opportunities for improvement.

• Lead infrastructure projects from planning and design through implementation, documentation, and ongoing support.
• Troubleshoot complex infrastructure, networking, cloud, and systems issues to minimize downtime and business impact.
• Develop and maintain infrastructure documentation, operational procedures, technical standards, and knowledge resources.
• Implement automation and monitoring solutions that improve operational efficiency, reliability, and scalability.
• Partner with vendors to ensure successful delivery and support of infrastructure services.

• Administer Windows Server, Active Directory, Azure Active Directory, Microsoft 365, and related enterprise systems.
• Support secure networking services including TCP/IP, DNS, DHCP, VPN, routing, switching, and wireless connectivity.
• Build and improve user onboarding, offboarding, device lifecycle, endpoint management, and asset management processes.
• Support security, patching, monitoring, access management, and infrastructure best practices across the technology environment.

• Support integrations between ERP, eCommerce, WMS, CRM, and third-party SaaS platforms.
• Develop and troubleshoot integrations using REST APIs, webhooks, JSON/XML, OAuth authentication, and related technologies.
• Support EDI transactions and trading partner integrations, including 850, 855, 856, 810, 940, and 945 transactions.
• Partner with business and technology teams to troubleshoot application integrations and ensure reliable data flow between systems.

• Partner closely with technology leadership and business stakeholders to understand requirements, prioritize initiatives, and communicate project status.
• Communicate technical concepts, risks, dependencies, and recommendations clearly to both technical and non-technical audiences.
• Mentor Tier 1 support staff by providing technical guidance, knowledge sharing, troubleshooting assistance, and best practices.
• Partner with vendors, consultants, and managed service providers to coordinate technical initiatives and resolve issues.
• Stay current on emerging technologies and recommend solutions that align with business objectives.

QualificationsWhat We Are Looking For:

• Bachelor’s degree in Information Technology, Computer Science, Network Engineering, or a related technical field preferred.
• 5+ years of experience administering enterprise infrastructure, distributed systems, or hybrid cloud environments.
• Strong hands-on experience with AWS, Microsoft Azure, Windows Server, Active Directory/Azure Active Directory, and Microsoft 365.
• Strong understanding of enterprise networking, including TCP/IP, DNS, DHCP, switching, routing, wireless networking, VPNs, and firewalls.
• Excellent troubleshooting, systems analysis, and problem-solving skills, with the ability to diagnose complex issues across infrastructure, networking, cloud, and business systems.
• Experience leading technical projects and working independently in a fast-paced, growing environment.
• Strong communication skills and the ability to collaborate effectively with both technical and business teams.

Experience with the follow is a plus:

• Infrastructure-as-code and automation using Terraform, Ansible, PowerShell, Python, Bash, or JavaScript.
• DevOps and CI/CD practices using Git or GitLab.
• Containerization and orchestration technologies such as Kubernetes or OpenShift.
• Virtualization platforms such as VMware ESXi, Hyper-V, or KVM.
• Integration platforms such as Boomi, Celigo, MuleSoft, Jitterbit, Zapier, or similar technologies.
• Designing and supporting integrations between ERP, eCommerce, WMS, CRM, and SaaS platforms.
• EDI transactions and trading partner integrations, including 850, 855, 856, 810, 940, and 945.
• REST APIs, webhooks, JSON/XML, OAuth, and Postman.
• Microsoft SQL Server and T-SQL, particularly in support of SAP Business One or other SQL-based business applications.
• Endpoint and device management platforms such as Addigy and Pulseway.
• UniFi networking, including switching, routing, and wireless infrastructure.
• Business and collaboration platforms including Google Workspace, Slack, Zoom, and Power BI.

The Technology You will work with

• Cloud & Infrastructure: AWS, Microsoft Azure, Windows Server, Microsoft 365, Active Directory/Azure Active Directory, virtualization, storage, monitoring, and hybrid cloud infrastructure.
• Networking & Security: UniFi networking, Azure VPN, switching, routing, wireless, firewalls, DNS, DHCP, TCP/IP, and endpoint security.
• Automation & DevOps: Git/GitLab, Terraform, Ansible, PowerShell, Python, Bash, CI/CD, and container technologies.
• Business Systems & Integrations: SAP Business One, SQL Server, Power BI, Boomi, Celigo, REST APIs, webhooks, JSON/XML, OAuth, and EDI.
• Endpoint & Collaboration: Windows, macOS, iOS, Addigy, Pulseway, Microsoft 365, Google Workspace, Slack, and Zoom.

We don’t expect every candidate to have experience with every technology listed above. We’re most interested in strong infrastructure fundamentals, excellent problem-solving skills, a willingness to learn, and the ability to work across a broad and evolving technology environment.