Main Sail, LLC

Lead Project Technician (Remote)

Main Sail, LLC • $90K — $120K *
US-AnywhereRemote in Chesterland, OH
Information Technology
5 - 7 years of experience
5 days ago
Job Overview by Ladders

Qualifications

  • 5+ years in systems engineering or M365 administration
  • Experience with Microsoft 365 deployment and management
  • Preferred experience in GCC and GCC High environments
  • Strong skills in Active Directory, networking, and Windows Server
  • Familiarity with CMMC, NIST 800-171 compliance frameworks is advantageous
  • Proficiency in PowerShell or similar scripting languages
  • Excellent documentation and organizational skills

Responsibilities

  • Perform SharePoint Online migrations with a focus on data integrity
  • Lead or participate in network builds and server configurations
  • Support deployment of security solutions across various environments
  • Assist in advanced troubleshooting for escalated support issues
  • Mentor lower-tier tech team members as needed
  • Aid in CMMC compliance and documentation during client onboarding
  • Contribute to standard operating procedures and technical documentation

Benefits

  • Opportunities for mentorship and professional growth
  • Exposure to leading technologies in cloud and on-premises environments
  • Ability to influence process improvement initiatives
  • Collaborative team-driven work environment
Full Job Description
About the Job

Lead Project Technician - (Exchange Online, on-premises Exchange, third-party systems).

  • Perform SharePoint Online migrations, ensuring data integrity and user access continuity.


Project Execution:

  • Participate in or lead infrastructure projects such as network builds, workstation migrations, server builds, and tenant reconfigurations.
  • Support the deployment and configuration of security and compliance solutions across environments.


Support Collaboration:

  • Assist the Support Department with escalations that require advanced troubleshooting or project-level expertise.
  • Mentor Tier I and Tier II team members when needed.


CMMC Support:

  • Assistance with CMMC/Client On-Boarding.
  • Working with clients as tenant is built through implementation phases.
  • Support ongoing CMMC compliance activities, including system maintenance, audit preparation, and documentation updates.
  • Implement and maintain required security controls and configurations in client environments.


Process Improvement:

  • Contribute to the creation and refinement of standard operating procedures, automation scripts, and technical documentation to improve efficiency and consistency.


Qualifications & Skills:

  • 5+ years of hands-on experience in systems engineering, infrastructure projects, or M365 administration.
  • Proven experience deploying and managing Microsoft 365 (Exchange Online, SharePoint Online, Intune, Entra ID/Azure AD).
  • Experience with GCC and GCC High environments highly preferred.
  • Strong background in Active Directory, networking, and Windows Server environments.
  • Familiarity with CMMC, NIST 800-171, or other compliance frameworks is a plus.
  • Proficiency in PowerShell or other scripting languages for automation.
  • Excellent documentation, organization, and communication skills.
  • Ability to manage multiple projects simultaneously and work effectively in a team-driven environment.


Preferred Certifications:

  • Microsoft 365 Certified: Enterprise Administrator Expert.
  • Microsoft Certified: Security Administrator Associate.
  • CompTIA Security+ or equivalent cybersecurity certification.
  • Any CMMC, NIST, or compliance-related certification (preferred).

About Main Sail, LLC

Main Sail, LLC is a hospitality company that provides vacation rental management services. The company was founded in 2014 and is based in Austin, Texas. Main Sail's platform allows property owners to list their properties on various vacation rental websites, such as Airbnb and VRBO, and manage their bookings and reservations. The company also provides cleaning and maintenance services for vacation rental properties. Main Sail's mission is to help property owners maximize their rental income and provide a seamless vacation rental experience for guests.
Learn more about Main Sail, LLC
Size
100 employees
Industry
Hospitality & Recreation
* Ladders Estimates

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