Remote IT Operations Leader: Cloud, MSP & Security

OUTDOOR LIVING SUPPLY LLC; Milton (MA); Remote; USD 115,000 - 130,000; Full time

Benefits offered by this job

Medical, Dental, and Vision Insurance

Company-paid Life Insurance

Company-paid Long-Term Disability (LTD

Legal/ID Shield Coverage

Paid Time Off and Company Holidays

Job summary

Outdoor Living Supply LLC is seeking a hands-on Manager, IT Operations to lead our technology infrastructure, outsourced IT support, and service providers across our growing U.S. footprint.

You will oversee networks, Wi‑Fi, servers, cloud infrastructure, Microsoft 365, identity management, and security initiatives, while partnering with location teams to improve reliability and cost efficiency. This role reports to the CIO and requires strong collaboration and vendor management.

Qualifications

• 10+ years IT experience including IT operations, infrastructure, service delivery, and leadership.
• Broad knowledge of enterprise networking, cloud infrastructure, Microsoft 365, identity management, and operations.
• Experience managing outsourced IT services, MSPs, and third-party vendors.
• Strong incident management, service delivery, performance metrics, and improvement skills.
• Bachelor’s degree preferred; equivalent experience accepted; IT certifications are a plus.

Responsibilities

• Keep services reliable, secure, and efficient across all locations; drive technology improvements.
• Oversee networks, Wi‑Fi, servers, cloud infrastructure, and telecommunications.
• Manage Microsoft 365, identity management, collaboration tools, and MSP IT management.
• Identify risks and coordinate improvements for reliability, efficiency, and scalability.
• Lead infrastructure initiatives with project management and external providers.
• Manage relationships with MSPs, SaaS admins, security providers, and consultants.
• Set service expectations and monitor vendor performance; enforce accountability.
• Develop service standards and reporting on quality and issues.
• Support incident coordination and escalation with responsible teams.
• Partner with security providers to implement effective security measures.
• Advise CIO on planning, vendor performance, and cost efficiency.
• Build cross-functional relationships to drive improvements.

Skills

IT operations leadership

Infrastructure management

Vendor management

Incident management

Service delivery optimization

Microsoft 365 administration

Networking & cloud infrastructure

Identity management

Education

Bachelor’s degree preferred

Tools

Microsoft 365 admin tools

Job description

Outdoor Living Supply LLC is seeking a hands-on Manager, IT Operations to lead our technology infrastructure, outsourced IT support, and service providers across our growing U.S. footprint.

You will oversee networks, Wi‑Fi, servers, cloud infrastructure, Microsoft 365, identity management, and security initiatives, while partnering with location teams to improve reliability and cost efficiency. This role reports to the CIO and requires strong collaboration and vendor management.