IT Systems Administrator

Employee Navigator•Bethesda, MD

2d•$60,000 - $95,000

About The Position

Employee Navigator is a rapidly growing and highly profitable $100M ARR SaaS insurance & HR technology company that works with the nation’s leading insurance carriers, payroll companies & insurance brokers. Our products are designed to make it easier for our customers to manage the complexity of employee benefits & HR including benefits administration, employee onboarding and much more. Employee Navigator is the leading broker-centric benefits administration and HR platform in the US serving over 175,000 companies. We’ve been recognized as one of The Washington Post’s Top Workplaces for eight consecutive years — and in 2025, we proudly earned our first Top Workplace award in Salt Lake City in our very first year of eligibility. Join us to help carry on our award-winning culture and be part of building something new and meaningful here! About the Role Data security and efficient IT operations are important to us and as a result we are looking for a sharp candidate with a strong IT troubleshooting and systems administration background to support our growing organization and help strengthen our IT practices. The IT Systems Administrator will support our organization in a number of ways including Microsoft 365 and Azure administration, device management through Intune and Apple MDM, improving IT workflows, and managing hardware logistics. Our ideal candidate will be a critical thinker who consistently seeks to improve processes and their own knowledge, strives for high-quality work, genuinely wants to help others, and is looking for a long-term place to grow their career. We’re looking for individuals to join the team who very much want to know why something happened in addition to just that it happened. We have a lot of ideas but are hopeful your perspective will push us forward together to deeper understanding.

Requirements

3–5 years of experience in IT administration, systems support, or similar technical roles
Experience working in an ITSM tool or ticketing system
Strong hands-on experience with Microsoft 365 and Azure AD administration, including identity management and security configuration
Experience managing devices at scale using Intune, Apple Business Manager, and MDM platforms (macOS and Windows)
Proficiency with PowerShell for automation, reporting, and system configuration
Experience supporting and troubleshooting macOS and Windows hardware, conferencing tools, and peripherals
Ability to mentor and guide IT Specialists and elevate the team's overall technical capability
Strong customer service and communication skills, including the ability to support executives with a polished, white-glove approach and to understand needs even when not expressed directly
Willingness to assist with basic tasks when needed while maintaining focus on broader system and process improvements
Ability to learn new technologies quickly and adapt processes accordingly
Solid understanding of RBAC, IAM, MFA, conditional access, and modern identity and access security
Proven ability to identify opportunities for automation, process improvement, and workflow optimization
Working knowledge of IT security principles, risk vectors, and common vulnerabilities

Responsibilities

Take ownership of IT operations, systems administration, and technical projects for the Bethesda office, with a focus on improving and maturing operational processes
Serve as an escalation point for remote and on-site technical issues, supporting IT Specialists and guiding them through complex troubleshooting
Lead management of Intune, Apple Business Manager, and other MDM platforms, including device compliance, configuration policies, and deployment workflows
Develop and refine device provisioning processes for macOS and Windows, leveraging automation, scripting, and modern management practices
Provide advanced support through the ticketing system, focusing on root-cause analysis, long-term remediation, and documenting solutions for the broader team
Oversee onboarding and offboarding workflows, improving account creation, access provisioning, and device setup
Maintain and enhance hardware lifecycle management, including inventory systems, procurement processes, and device retirement plans
Administer corporate Microsoft 365 and Azure environments, including user identity, access controls, conditional access, licensing, and security configuration
Create, update, and improve IT documentation, playbooks, and technical standards to support a consistent and scalable IT environment
Research and evaluate new tools, technologies, and best practices; propose and implement improvements to enhance security, reliability, and efficiency
Support office infrastructure such as networking, cabling, Wi-Fi troubleshooting, and AV systems, stepping in for more complex or advanced tasks
Assist with configuration and maintenance of enterprise switches, firewalls, and network appliances as needed
Support office expansions or relocations by helping plan and coordinate IT infrastructure setup, device deployment, and connectivity requirements
Assist with projects at other office locations (occasional travel required)
Collaborate closely with Security, Engineering, HR, and other teams on cross-functional initiatives, providing system expertise and guidance