Remote Tech Jobs in Kennebunk, ME (NOW HIRING)

WIN Waste Innovations is seeking a Senior Systems Administrator to support its corporate office and facilities. This role will focus on Microsoft cloud infrastructure and Microsoft Entra, including Office 365, Exchange Online, and Intune for endpoint management, as well as systems administration and automation. Key responsibilities will include software packaging, endpoint deployments, user support, management of Azure services (such as Teams and SharePoint), vendor management, and oversight of Microsoft licensing.

This role requires both independent and collaborative work, encompassing systems and cloud administration, infrastructure design, and project management. Duties include planning for service outages, resolving infrastructure issues, maintaining servers and workstations, performing system backups, providing disaster processes, and ensuring security and integrity of systems and data.

The Senior Systems Administrator will follow established best practices, improve IT policies, evaluate new technologies, and provide technical support locally and remotely. Additionally, the role includes educating IT professionals and end users, documenting procedures, monitoring systems for anomalies, and maintaining operating system security. The position demands senior-level expertise and the ability to handle a range of assigned tasks.

Responsibilities

• Act as a subject matter expert for Microsoft 365 and Azure AD services, including Exchange Online, Teams, SharePoint, and OneDrive, delivering advanced support and guidance to both end users and IT staff.
• Manage, maintain, and improve the Microsoft 365 environment, including user accounts, permissions, licensing, security, compliance, and legal hold activities.
• Support for identity and access management includes Entra ID Connect, MFA, Conditional Access, and synchronization with on-premises Active Directory.
• Administer endpoints and devices using Intune and related MDM tools, including imaging, software packaging, deployment, and lifecycle management.
• Support for on-premises, cloud, and remote infrastructure, which includes servers, workstations, and essential enterprise services.
• Ensure the security, reliability, and integrity of systems and data by supporting email security, conducting backups, managing vulnerabilities, and triaging cybersecurity events.
• Provide second-level and escalation support to Service Desk agents and other staff for issues that require deeper troubleshooting or urgent resolution.
• Develop and maintain automation processes and improvements using PowerShell scripting, Power Automate, and other related Microsoft tools.
• Document the systems, configurations, and procedures thoroughly. Create clear documentation for both users and IT support.
• Assess, test, and implement emerging technologies to enhance Microsoft 365 and enterprise systems.
• Work collaboratively with vendors, internal teams, and business stakeholders to provide reliable and scalable IT services.
• Be available for after-hours support and travel to company facilities as needed.
• This role is not hybrid or fully remote; you are primarily expected to be on-site to support users and systems, although we do offer some flexibility for remote work.

Skills, Qualifications, & Experience

• A Bachelor's degree in an IT-related field or 5+ years of equivalent experience.
• Minimum of five years of experience in a senior technical support role.
• Familiarity with ITIL processes and methodologies.
• Strong technical background.
• Excellent analytical and troubleshooting skills.
• Ability to work under pressure.
• Excellent leadership and mentorship skills.
• Strong customer service skills.
• Experience with Microsoft Office 365 core suite of applications.
• Experience with computer software license management and asset controls.
• Familiarity with Windows computer deployment practices (i.e., Intune).

Personal Attributes

• A disciplined self-starter capable of completing projects with minimal direction.
• An effective team player who collaborates well with clients and colleagues.
• Strong organizational and time management skills, able to manage multiple tasks simultaneously.
• Excellent communication and documentation abilities.
• Ability to thrive under pressure in a fast-paced environment with strong prioritization skills.

What You'll Enjoy:

• Competitive annual bonus
• Industry leading benefits
• Multiple and flexible medical plans
• Outstanding PTO program
• Floating Holidays
• Strong 401k program and company match
• Tuition reimbursement plan
• College loan reimbursement
• College scholarship program for dependents
• Parental Leave Program
• Inclusive culture
• Employee engagement events
• Employee resource groups

WIN Waste Innovations is a waste management company committed to delivering essential waste management solutions to customers and communities supported by our team of 2,300 employees. We believe in preserving our environment for future generations while providing for today's needs. WIN Waste Innovations is a vertically integrated business with a platform of 50 strategically located collection, transfer, and disposal assets. These include waste-to-energy facilities, transfer stations, ash monofills, landfills, and fleets of rail cars and collection vehicles. We process more than 11 million tons of waste annually, converting 6.7 million tons of waste into clean, renewable energy that powers 340,000 homes. We recycle more than 234,000 tons of plastic, paper, and metals from the waste stream.

At WIN Waste Innovations, each eligible employee receives a competitive total compensation package including Medical, Dental, Vision, Life Insurance and Short-Term Disability. As well as Company match on 401K, and more! Our employees also receive Paid Vacation, Holidays, and Personal Days. Please note that benefits may vary by site. Equal Opportunity Employer Minorities/Women/Protected Veterans/Disabled.