Senior MSP Engineer – IT Strategy & Systems (Client-Facing)
Full-Time | Hybrid WFH | Skokie, IL | $115,000–$130,000
We’re a boutique Managed Services Provider (MSP) that helps small and mid-sized businesses align technology with real business outcomes. Our team combines technical depth with strategic thinking—and we’re growing.
We’re looking for a Senior System Administrator with a background working for MSPs and strong client-facing experience to serve in a hybrid Senior System Administrator / vCIO capacity. This is a hands-on, high-impact role focused on systems, cloud, and IT strategy. If you enjoy solving complex technical problems while advising clients on how to scale and secure their infrastructure, this could be a great fit.
What You’ll Do:
- Design and present strategic IT roadmaps that align with each client’s business goals
- Lead technology projects—migrations, network upgrades, virtualization—from planning through deployment
- Serve as the primary point of contact for strategic IT decisions across multiple clients
- Administer and support Microsoft 365, Azure (VMs, Entra ID), and Intune environments
- Provide high-level support for Windows Server, networking (firewalls, VLANs, VPNs), and endpoint security tools
- Collaborate with internal engineers to troubleshoot issues, resolve escalations, and ensure high service quality
- Ensure all deployments and services follow MSP best practices and documentation standards
- Help clients improve their cybersecurity posture, infrastructure resilience, and cloud adoption
What You Bring:
- 1 year minimum of experience in a Managed Services Provider (MSP) environment
- Experience in client-facing roles such as vCIO, Sr. Systems Engineer, or Technical Account Manager
- Strong technical background across Microsoft 365, Azure, Intune, and virtualization platforms (VMware, Hyper-V)
- Familiarity with firewalls (Fortinet, Meraki), switches, VLANs, and VPN configuration
- Strong written and verbal communication skills with the ability to explain tech to business leaders
- Knowledge of cybersecurity principles and compliance frameworks (HIPAA, NIST, etc.) is a plus
- Proven success managing IT transformation projects or cloud migrations
- Highly organized, self-directed, and comfortable juggling multiple clients and priorities
Compensation:
- Competitive salary: $115,000–$130,000 (depending on experience)
- 100% employer-paid medical, dental, and vision coverage (with premium plan options)
- 401(k) with 3% company match
- 15 PTO days + all federal holidays + your birthday off
- Paid certification training and ongoing career development
- Gym membership reimbursement
- Mileage reimbursement for any client travel
- Hybrid flexibility: 1 day onsite, 4 days remote (after 30-day onboarding period)
