System Administrator and Security Analyst (MSP)

We are a well-established MSP / MSSP in Chicago’s West Loop is hiring a System Administrator and Security Analyst to support a mix of Commercial Real Estate, Residential, and Vacation Rental clients. This is a small and highly collaborative team where everyone wears multiple hats, learns quickly, and leverages modern cloud and security tooling. The role is ideal for someone who enjoys frontline support, real security responsibilities, and the chance to grow in multiple directions.

You will handle daily MSP tickets, lead frontline security response, and work extensively inside Datto RMM, Microsoft 365, Windows, and endpoint protection platforms. Responsibilities include resolving user issues, managing onboarding and offboarding, responding to phishing and malware alerts, maintaining patching through Datto RMM, applying Intune and Entra ID templates, running KnowBe4 campaigns, and helping senior engineers maintain secure and stable client environments. Occasional onsite visits may occur which is why this person must live in the Chicagoland area.

Requirements

• Two or more years of hands on MSP experience

• Strong Microsoft 365 and Windows troubleshooting skills

• Experience with Datto RMM or similar RMM platforms

• Experience with SentinelOne or similar endpoint security tools

• Comfort handling phishing, malware, and basic incident response

• Curious and security minded with a willingness to learn

• Confident communicating with clients at a foundational level

• Self starter who enjoys problem solving

Key Outcomes

• Resolve MSP tickets efficiently and accurately

• Own security alerts and contribute to incident response

• Maintain healthy RMM monitoring, patching, and remediation

• Support secure client environments using Intune and Entra ID templates

• Contribute to security awareness efforts through KnowBe4

• Collaborate closely with senior engineers and grow cross functionally

Benefits

• Health and dental coverage

• Retirement plan

• Small, tight knit team with a customer first culture

• Significant exposure to security operations

• Hands on experience with modern MSP tools and cloud technologies