Job Description

About Employee Navigator

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.

Here’s What you’ll do day-to-day:

• 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

Minimum Qualifications

• 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

The expected hiring range for this position is $60,000-$95,000 p/year. This range represents the company’s good-faith estimate of the salary at the time of posting. The actual pay may vary based on factors such as the candidate’s experience, skills, qualifications, and location, as well as internal equity.

We offer a comprehensive benefits package designed to support our employees’ professional growth and personal well-being. Our benefits include paid time off, Volunteer Time Off, 401(k) with company match, medical, dental, and vision insurance, disability coverage, educational reimbursements, and paid parental leave. To learn more about our benefits, visit our careers page

Employee Navigator does not discriminate based on race, religion, sex, sexual orientation, age, disability, or any other protected characteristic under applicable law.

Maryland Salary Range $80,000—$100,000 USD