Entry Level Redbird Jobs (NOW HIRING)

Redbird Security is a security-first MSP that serves one industry: independent insurance agencies across the United States. We keep agencies running, protect them from threats, and support their people with technology that works.

We are hiring a Technical Support Specialist for our service desk. This is a strong fit for an early-career IT professional who enjoys solving problems, helping people, and learning quickly.

Most companies would call this a Tier 1 role. We do not run rigid tiers. You will work alongside experienced technicians who value communication, documentation, and ownership.

What You Will Do:

Respond to client requests by phone, email, ticket, and remote session

Troubleshoot Windows 11, Microsoft 365, workstations, printers, mobile devices, and connectivity

Administer Microsoft 365 and Entra ID: accounts, password resets, MFA, licensing, groups, and access

Support secure remote access, endpoint protection, and application control with guidance from senior techs

Learn agency technology: Applied Epic, HawkSoft, AMS360, and related line-of-business applications

Work daily in PSA, RMM, remote control, and documentation tooling

Document clearly, follow SOPs, build the knowledge base, and own client communication through escalation

Support is delivered remotely from our Menomonee Falls office. Client-site travel is very limited.

What You Bring:

Clear verbal and written communication with a client-first mindset

Working knowledge of Windows 11, Microsoft 365, hardware, and basic networking

Organization and the judgment to prioritize in a fast-moving queue

Curiosity, humility, and follow-through

What Will Help You Succeed:

CompTIA A+, Network+, or Security+ certifications; experience in a service desk, MSP, technical support, or customer-facing environment; familiarity with Microsoft 365 technologies such as Entra ID, Intune, Defender, Exchange Online, SharePoint, and Teams; a solid understanding of networking fundamentals including TCP/IP, DNS, DHCP, wireless, firewalls, and secure remote access; and hands-on experience with EDR, application control, PSA, or RMM platforms.

What We Offer:

Pay based on experience, certifications, and demonstrated ability

Health, dental, and vision insurance

Retirement plan with company match

Certification reimbursement and real professional development

A team that values learning, accountability, and doing the work right

A clear path into Microsoft 365 administration, systems administration, project work, security operations, or service leadership

Redbird Security helps independent insurance agencies reduce downtime, strengthen security, support their teams, and keep the business moving without the constant drag of IT problems, vendor confusion, or preventable risk.
We combine managed IT, managed security, help desk support, Microsoft 365 protection, cyber risk reduction, and practical IT strategy into one clear plan built around your agency’s daily operations.

Our focus is simple:
Fewer disruptions so your team can stay productive.
Stronger protection for your users, devices, systems, and sensitive client data.
Better support from a team that takes ownership instead of leaving you stuck between vendors and unanswered tickets.
We understand the agency systems and vendor relationships that shape daily operations, including platforms like Applied Epic, HawkSoft, and AMS360. That helps us solve problems faster, improve workflows, and reduce pressure on your team.
For agencies that cannot afford downtime, weak security, or IT guesswork, Redbird Security provides the structure, protection, and support to keep the business moving.