IT Systems Engineer

Summary

Join Ditto, a fast-growing startup, as an IT Systems Engineer to manage and enhance core internal infrastructure. You will be responsible for macOS endpoint fleet management, network configuration and maintenance, infrastructure support in specialized environments, and global device procurement. This role involves developing automation scripts, overseeing secure access management, partnering with security teams, and supporting software audits. You will also contribute to documentation and self-service resource creation. This is a project-heavy role focused on scalable solutions, not routine support, reporting directly to the IT Manager.

Requirements

• 5+ years of hands-on experience in Systems Administration or IT infrastructure roles
• Deep expertise with macOS and MDM tooling (Mosyle, Kandji, or Jamf), including scripting and automation
• Strong knowledge of networking fundamentals: VLANs, VPN, firewalls, DNS, DHCP, QoS
• Experience with Unifi systems and remote/branch office infrastructure
• Experience with procurement systems and lifecycle planning (Zip experience is a plus)
• Solid understanding of SaaS ecosystems, SSO, RBAC, endpoint security, and compliance tooling
• Comfortable scripting in Bash, Python, or similar for task automation
• Excellent documentation hygiene and cross-functional communication skills
• A builder’s mindset and bias toward clarity, autonomy, and iteration

Responsibilities

• Manage macOS endpoint fleet using Mosyle or similar MDM (e.g., Kandji, Jamf), including zero-touch setup and policy enforcement
• Own configuration, expansion, and maintenance of Unifi-based Wi-Fi, VLANs, firewalls, VPN, and remote access systems
• Build and support infrastructure in specialized environments supporting our product
• Administer and secure a smaller set of non-Mac systems (Linux, iOS, Android, occasional Windows)
• Develop automation scripts for provisioning, deprovisioning, patching, and configuration
• Oversee global device procurement and own a global equipment retrieval and distribution process for remote hires, offboarding, RMAs, and replacements
• Maintain reliability of network and CI/CD-adjacent services across physical and virtual systems
• Support secure access management workflows via Okta, Google Workspace, and other SaaS tooling
• Partner with Security to maintain compliance tools like Drata & SentinelOne
• Support quarterly software audits to reduce SaaS waste and shadow IT
• Develop tooling/scripts to streamline routine SaaS and identity tasks
• Act as escalation point for complex issues (networking, provisioning, systems failures)
• Write and maintain SOPs, runbooks, and process documentation
• Contribute to service cataloging and self-service resource creation to reduce support friction

Preferred Qualifications

• Experience working with on-prem CI/CD hardware environments
• Familiarity with SOC 2 / ISO27001 readiness
• Experience designing asset workflows across multiple geographies
• Federal or high-compliance environment exposure

Benefits

• Competitive salaries
• Stock options
• Medical, dental, vision, life, and disability coverage
• Flexible spending account (FSA)
• Flexible vacation policy
• 401(k) plan