Remote Technical Support Engineer (Freelance / On-Call)

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We are seeking an experienced and highly skilled Remote Technical Support Engineer to provide on-demand support for our growing team. You should be available for approximately 5–10 hours per month, with the flexibility to take on additional project-based work as needed. The ideal candidate will have in-depth knowledge of email and domain management, experience supporting both Windows and Mac environments, and a proven track record diagnosing and resolving complex IT issues. Key Responsibilities: Immediate Project: • Develop and implement a comprehensive migration plan to move email services from Intermedia to Outlook, ensuring no workflow disruptions or data loss. • Deliver a scope of work (SOW) by 3pm EST on 3/12 that outlines the timeline, resources, and potential challenges for this migration. Ongoing Support & Projects: • Provide remote technical support and troubleshooting via phone, email, and remote desktop tools. • Set up and configure new user accounts, distribution lists, shared drives, and shared calendars (on both Windows and Mac machines). • Diagnose and resolve issues related to Outlook connectivity, folder syncing, and account management (including archiving, shared mailboxes, and advanced configuration). • Manage DNS records and domain configurations (MX records, A records, SPF, DKIM, etc.) for email services. • Investigate and resolve storage, backup, and security concerns (e.g., Carbonite backup errors, data migration, spam deliverability, network connectivity). • Collaborate with internal staff or external vendors (e.g., Intermedia) to troubleshoot escalated issues and optimize workflows. • Document all solutions, processes, and best practices to streamline ongoing support efforts. Required Skills & Qualifications: Technical Expertise: • Proven experience with email migrations (preferably Intermedia to Outlook/Office 365). • Proficiency with both Windows (10/11) and macOS environments, including Microsoft Office 365 suite and/or Exchange-based services. • Solid understanding of domain and DNS management (especially for email deliverability and hosting integrations). • Familiarity with remote support tools (e.g., TeamViewer, Remote Desktop, etc.) and basic network troubleshooting. Communication & Collaboration: • Comfortable leading phone/Zoom sessions, asking clarifying questions, and guiding less-technical stakeholders through complex processes. • Strong written communication skills for documentation and clear status updates. Problem-Solving: • Ability to diagnose and solve advanced technical issues in a systematic and efficient manner. • Resourceful, self-starter mentality; able to handle unexpected challenges without a lot of oversight. Nice-to-Have Experience: • Exposure to backup solutions such as Carbonite or similar platforms. • Knowledge of cloud collaboration tools (e.g., Google Workspace, Calendly integrations, Slack, or Asana). • Familiarity with older or specialized software (e.g., Microsoft Silverlight) and solutions for compatibility in modern browsers. • Basic web maintenance or CMS familiarity (e.g., occasional website DNS record checks, SSL certificate troubleshooting).

Keyword: Customer Support

Contractor Tier: Hourly: $18.00 - $31.00

Price: $18.0

Desktop & Laptop Support Email Support End User Technical Support Technical Support Microsoft Windows macOS Bug Reports Incident Management Troubleshooting System Configuration