IT & Systems Administrator

About benefitbay®

benefitbay is a leading SaaS company dedicated to the delivery of personalized benefits to the modern workforce. Our innovative platform simplifies the deployment/delivery of Individual Coverage Health Reimbursement Arrangements. Our platform also offers robust analysis and banking tools to support employers transitioning to ICHRA model of employee benefits.

Role Overview

We are seeking a hands-on IT & Systems Administrator to own and scale our internal technology environment. This individual will be responsible for delivering reliable, high-quality IT support while building a modern, secure, and scalable foundation for a growing organization.

This is a highly impactful role that blends day-to-day IT support, endpoint and identity management, and systems ownership. Over time, this role will expand to support and optimize key business platforms, including HubSpot and SharePoint.

Key Responsibilities

IT Support & Operations

· Serve as the primary point of contact for all internal IT support needs across ~80

employee users today and rapid expansion in next 6 months.

· Provide hands-on troubleshooting for hardware, software, and access issues

(macOS/Windows environments)

· Manage onboarding and offboarding processes, including device provisioning and access controls

· Maintain IT documentation, knowledge base, and support workflows

· Establish SLAs and continuously improve support responsiveness and employee

experience

· Occasional after-hours availability expected for critical incidents

Endpoint & Identity Management

· Own and administer endpoint management tools (e.g., Addigy, Microsoft Entra)

· Manage device compliance, patching, software deployment, and security configurations

· Administer identity and access management, including SSO, MFA, and role-based access controls

· Oversee device lifecycle management (procurement, configuration, inventory,

decommissioning)

Systems Administration

· Administer Microsoft 365 (O365), including Exchange, Teams, SharePoint, and user management

· Manage VPN access and configuration

· Maintain and optimize cybersecurity tooling (endpoint protection, monitoring,

access controls)

· Partner with leadership to ensure systems are secure, compliant, and scalable

Cybersecurity & Risk Management

· Implement and maintain security best practices across endpoints and systems

· Monitor and respond to security alerts and incidents

· Support compliance initiatives (e.g., SOC 2, HIPAA, or similar frameworks if

applicable)

· Drive security awareness and training across the organization

· Work with our security team to ensure security and reporting needs are met

HubSpot & SharePoint (Growth Area)

· Provide Tier 1–2 support for HubSpot and SharePoint users

· Troubleshoot user issues, permissions, and basic workflows

· Partner with teams to improve system usability and data integrity

· Develop increasing ownership of HubSpot and SharePoint administration over

time

· Evaluate and support additional tools as the business scales

Qualifications

Required

· 5+ years of hands-on IT support or systems administration experience

· Experience replacing or working alongside an MSP in a growing company environment

· Strong experience with:

o Endpoint management tools (e.g., Addigy, Intune, etc.)

o Identity management platforms (Microsoft Entra / Azure AD or

equivalent)

o Microsoft 365 administration

· Experience managing VPNs, endpoint security tools, and access controls

· Strong troubleshooting skills across hardware, OS, and SaaS applications

· Ability to operate independently in a fast-paced, scaling environment

· Ability to observe a PTO blackout period from November – January

Preferred

· Experience with HubSpot and SharePoint administration or support

· Exposure to SaaS business environments and GTM systems

· Experience supporting compliance frameworks (SOC 2, HIPAA, etc.)

· Familiarity with automation tools and IT workflows (e.g., scripting, Power Automate, etc.)

Why Join benefitbay®

· Join a fast-growing company that is entering a high-growth stage

· Build an internal IT function from scratch as we transition off our MSP

· Work alongside a team deeply invested in service, data integrity, and innovation

Location: Remote ~ Hybrid, with emphasis on location in Kansas City, MO

Department: Operations

How to Apply: Send cover letter and resume to HR@BENEFITBAY.COM

benefitbay® is an equal opportunity employer and makes employment decisions without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability status, or any other status protected by law.

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IT & Systems Administrator