Systems and Security Administrator (MSP)

We are a tight knit, growth focused Managed Service Provider supporting a mix of commercial real estate, residential, and vacation rental clients. The team is small, highly collaborative, and known for a white glove customer first approach using modern cloud and security tools. This is a place where you will wear multiple hats, learn fast, and make a real impact quickly.

We are hiring a Tier 2 Systems and Security Administrator with MSP experience who is comfortable jumping into tickets while also owning day to day security tasks. If you enjoy a blend of frontline support and real security work, this role gives you hands on exposure without being siloed.

What You Will Do

• Triage and resolve Tier 2 tickets across Microsoft 365, Windows, onboarding and offboarding, and basic networking

• Own security alerts and first response for phishing, malware, and endpoint threats

• Work daily in Datto RMM for patching, monitoring, alert response, and remote remediation

• Support endpoint security tooling including SentinelOne and Microsoft Defender

• Follow established templates for Intune and Entra ID policies and help with day to day administration

• Run KnowBe4 campaigns and support security awareness efforts

• Occasionally assist with small projects or rare onsite visits, about once per quarter

What You Bring

• 2 plus years of hands on MSP experience

• Strong Microsoft 365 and Windows troubleshooting skills

• Experience with Datto RMM preferred, Kaseya or NinjaOne also relevant

• SentinelOne experience strongly preferred

• Interest in security with a curiosity driven mindset and willingness to learn

• Comfortable communicating with clients and providing clear updates

• Self starter who focuses on solving problems, not just closing tickets

Location, Pay, and Benefits

• Chicago based, mostly remote with a small collaborative team

• Strong exposure to security operations and MSP tooling

• Broad role with learning from senior engineers and room to take on more over time

• Health and dental benefits plus an upcoming retirement plan

• Stable role with growth opportunity