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MSP Manager Chicago, IL HIPAA PSA/RMM USA Job level: Lead Department: Development Department Employment type: Full-time,B2B at OLSYS

Rakuten

OLSYS All vacancies (5)

Based on
Founded in

Details

Publication date

May 24, 2026

Closing date

June 24, 2026

Кар'єрний рівень

Lead

Освіта

Bachelor


ABOUT THE PROJECT

We are looking for a skilled and business-minded MSP Manager who combines strong technical expertise in IT support with leadership, process development, and client-facing soft skills. This role is critical for scaling our MSP operations, formalizing service offerings, shaping go-to-market strategies, and supporting business growth through market awareness and client engagement. This is a player-coach role where you’ll spend approximately: 40%

Strategic planning, process development, and team leadership 30% Client-facing activities (senior escalations, relationship management, pre-sales) 20% Hands-on technical work and mentoring 10%

Business development and marketing collaboration Requirements: Proven experience in IT support or MSP environments (minimum 5 years). Hands-on technical background (preferably with Windows environments and general infrastructure). Experience with PSA/RMM tools (ConnectWise, Datto, N-able, etc.), The current tool is ManageEngine.

Microsoft and Google ecosystems expertise (M365, Active Directory, Intune, Azure, Google Suite, GCP). Network infrastructure familiarity (firewalls, VPNs, VLANs, SD-WAN). Cybersecurity frameworks and tools (NIST, CIS Controls).

Backup/DR solutions (Veeam, Datto, etc.). Experience with compliance requirements (HIPAA, SOC 2, PCI-DSS). Strong understanding of business continuity, disaster recovery, security best practices.

Excellent communication and interpersonal skills ability to build rapport with clients and internal teams. Leadership experience, including mentoring and managing technical teams.

Commercial mindset with experience supporting growth initiatives, market analysis, or client-facing pre-sales activities. Ability to think strategically and contribute to pricing and marketing initiatives. Familiarity with AI-driven documentation tools is a plus.

Preferred Traits: Microsoft certifications (Azure Administrator, M365) CompTIA certifications (Security+, Network+) ITIL Foundation certification Proactive mindset with a desire to improve processes and scale operations. Comfortable navigating ambiguity and building structure from the ground up. Balanced skill set: strong technical base + business acumen + soft skills.

RESPONSIBILITIES
  • Team Leadership &amp
  • Operations Lead and mentor team of IT engineers and support staff
  • Define and formalize internal roles, processes, and escalation paths
  • Develop training programs and documentation practices
  • Client Management Act as

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