Independent Contractor Opportunity: Fractional IT Manager (1099)

We are seeking an experienced Fractional IT Manager to serve as the primary technology advisor and support resource for our growing insurance agency. This is a 1099 Independent Contractor opportunity for a self-directed IT professional who can provide ongoing technology management, cybersecurity oversight, Microsoft 365 administration, and responsive user support.

The ideal contractor will be available during normal business hours to respond to support requests, proactively manage our technology environment, and recommend improvements that help our business operate efficiently and securely.

Salary Range: $40.00 - $60.00 per hour


Benefits

Hourly Base Salary Based on Experience

Flexible Schedule

Work from Home


Responsibilities

Microsoft 365 Administration:

  • Administer and maintain Microsoft 365 services including:
  • Exchange Online
  • Microsoft Teams
  • OneDrive
  • Microsoft Entra ID (Azure Active Directory)
  • Microsoft Intune (preferred)
  • Manage user accounts, licensing, permissions, and security groups.
  • Configure and maintain Multi-Factor Authentication (MFA), Conditional Access, and security policies.
  • Support onboarding and offboarding of employees.

IT Support:

  • Provide remote support during normal business hours with same-day response for routine support requests.
  • Troubleshoot Windows PCs, Microsoft Office applications, printers, networking, and Internet connectivity.
  • Coordinate hardware replacement and repairs with vendors when necessary.
  • Schedule on-site visits as needed for equipment installations or complex issues.

Remote Operations & Communications Support:

  • Provide ongoing technical support for a small team of remote virtual agents based in the Philippines.
  • Administer and troubleshoot the agency's POPP Communications phone system and related call center technologies.
  • Coordinate user setup, access, and troubleshooting for remote staff, including Microsoft 365 accounts, email, Teams, and other business applications.
  • Ensure reliable connectivity between the home office, remote agents, and cloud-based business systems.
  • Support call quality, headset configuration, softphone applications, and remote workstation issues.
  • Coordinate with POPP Communications and other technology vendors to resolve service interruptions and technical issues.
  • Assist with onboarding and offboarding remote employees, including provisioning and deprovisioning user accounts and equipment.
  • Recommend and implement technology improvements that enhance productivity, communication, and customer service for the remote team.

Cybersecurity:

  • Monitor and improve the agency's cybersecurity posture.
  • Ensure systems are updated with security patches.
  • Manage endpoint protection and backup solutions.
  • Recommend and implement security best practices.
  • Assist with employee cybersecurity awareness.
  • Resolve any cybersecurity issues in a timely fashion.

Network & Infrastructure:

  • Maintain office network equipment, wireless access points, firewalls, and Internet connectivity.
  • Coordinate with Internet service providers and technology vendors.
  • Monitor system performance and recommend infrastructure improvements.

Technology Planning:

  • Serve as the agency's trusted technology advisor.
  • Recommend hardware and software upgrades.
  • Develop technology standards and documentation.
  • Assist with annual technology budgeting and planning.
  • In partnership with the Office Manager, manage and optimize agency technology services billing.
  • Maintain disaster recovery and business continuity documentation.

Vendor Management:

  • Manage relationships with software, telecommunications, and technology vendors.
  • Oversee software licensing and renewals.
  • Evaluate and recommend new technology solutions.

Requirements

Must be able to come into the office on an as needed basis. Fully remote candidates need not apply.

Preferred Qualifications:

  • Minimum 5 years of experience supporting small business IT environments
  • Advanced knowledge of Microsoft 365 administration
  • Experience with Windows 11 and Microsoft Office
  • Knowledge of networking, VPNs, firewalls and wireless system
  • Experience implementing cybersecurity best practices
  • Excellent troubleshooting and communication skills
  • Strong documentation and organizational skills
  • Experience supporting financial services or insurance organizations is preferred

Marketing Experience (Preferred):

  • Experience supporting or collaborating with marketing initiatives is a plus, including:
  • Website management and hosting
  • Answer Engine Optimization (AEO)
  • Social media platform support
  • CRM (AgencyBloc) and marketing automation systems

Notice to Third-Party Agencies:

Please do not contact us regarding this position. Unsolicited resumes sent to our company or employees will be considered property of the company, and no agency fees will be paid under any circumstances.


Remote

Skills:
Authentication, Automation Systems, Best Practices, Billing, Budgeting, Business Solutions, Business Support, Call Centers, Cloud Computing, Communication Skills, Computer Workstations, Customer Relationship Management (CRM), Customer Support/Service, Disaster Recovery, Documentation, Endpoint Security, Equipment Maintenance/Repair, Financial Services, Firewalls, Hardware Repair, Hardware Upgrades, Identify Issues, Information Technology & Information Systems, Insurance, Internet Security, Internet Service Providers, Licensing, Management of Information Systems/Technology (MIS), Marketing, Marketing Automation Software, Microsoft Access Database, Microsoft Active Directory, Microsoft Exchange Server, Microsoft Office, Microsoft Product Family, Microsoft Windows Azure, Microsoft Windows Operating System, Network Administration/Management, Network System Hardware, Office Equipment, Office Management, Onboarding, Operational Communications, Operational Support, Organizational Skills, Performance Analysis, Problem Solving Skills, Productivity Management, Relationship Management, Security Patches, Small Business, Social Media, Software Licenses, Software Upgrades, Standards Development, Systems Maintenance, Technical Leadership, Technical Support, Telecommunications, Time Management, User Account Administration, VPN (Virtual Private Network), Vendor/Supplier Management, Web Hosting, Website Management, Wireless Communications, Work From Home


CAL Financial, Inc.



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