IT Desktop Support & Systems Standardization Assistant

IT Desktop Support & Systems Standardization Assistant Remote | Part-Time | Long-Term Potential | Law Firm / Professional Services Environment Key Details Role Type: Remote independent contractor Hours: 20-35 hours per week Compensation: $5/hour (rate may be reduced by 10% if assistant is not available to work at least 20 hours/week if requested by the firm) Future Raises: position eligible for consideration for $1/hour raise on January 1 for someone who proves precise, reliable, and capable of working independently. Schedule: Part-time, with required availability during U.S. Pacific Time sync hours Mandatory Sync Hours: 7:00 AM – 2:00 PM Pacific Time, as scheduled and needed Location: Fully remote; international candidates are welcome Time Tracking: Upwork hourly contract with required time tracking, accurate work diary entries, activity tracking, and periodic screenshots Communication Tools: Zoom, Zoom Chat, ClickUp, Microsoft 365 Primary Systems: Microsoft 365, Windows 11 Pro, Dell business PCs, Surface laptops, NetDocuments, OneDrive, SharePoint, ClickUp, Zoom, browser-based SaaS tools, and approved security/endpoint tools Position Overview We are looking for a detail-oriented IT Desktop Support & Systems Standardization Assistant to help support, document, and improve the technology setup used by a fully remote U.S.-based business law firm. This role will begin with a specific project: helping coordinate and document the setup of a new primary desktop workstation for the firm owner. The workstation will likely be a Dell Pro Micro Plus Desktop with three external monitors, Windows 11 Pro, Microsoft 365, NetDocuments, OneDrive, SharePoint, ClickUp, Zoom, and other SaaS tools used by the firm. The broader goal is to create a repeatable, standardized IT setup process that can be used for future computer purchases and setups across the firm. This person will not replace our existing IT vendor or internal IT support. Instead, this person will help coordinate implementation, create checklists, document configurations, test workflows, and ensure that technology setups are completed with precision and follow-through. We are looking for someone who is careful, organized, coachable, security-conscious, and willing to take ownership of details. Core Mission The mission of this role is to help ensure that firm technology is: • Properly configured; • Secure; • Well-documented; • Standardized across users where appropriate; • Easy for attorneys and staff to use; • Reliably connected to the firm’s cloud-based systems; • Not dependent on files or settings that live only on one local computer. The ideal candidate will help us move from ad hoc computer setup to a more mature, repeatable endpoint setup and support process. Initial Project: Firm Owner Desktop Workstation Setup The first major project will involve assisting with the setup plan for a new desktop workstation for the firm owner’s home office. Expected setup includes: • Dell Pro Micro Plus Desktop or similar business-class Windows desktop; • Windows 11 Pro; • Three external monitors; • Hardwired Ethernet connection; • Wi-Fi enabled for mobile hotspot backup; • Bluetooth configured for approved peripherals; • Microsoft 365 Apps; • Outlook; • OneDrive for Business; • SharePoint access; • NetDocuments / ndOffice; • ClickUp; • Zoom and Zoom Chat; • PDF software; • legal research and AI-related browser tools; • approved browser profiles and bookmarks; • password manager or approved credential workflow; • endpoint security, device encryption, and update controls; • clean file-location rules so important files do not live only on the local device. The selected candidate will help turn the workstation requirements into practical setup checklists, implementation steps, testing procedures, and documentation. Longer-Term Role After the initial workstation project, this role may expand into ongoing support for firmwide IT standardization. Longer-term projects may include: • Creating a standard computer setup checklist for new team members; • Creating standard configurations for future laptop and desktop purchases; • Helping document recommended Dell / Surface / Windows configurations; • Maintaining a software access checklist by role; • Helping standardize Microsoft 365, OneDrive, SharePoint, NetDocuments, ClickUp, and Zoom setup expectations; • Coordinating with the firm’s existing IT vendor; • Helping prepare new computers for attorneys and staff; • Assisting with basic desktop support questions; • Creating troubleshooting documentation; • Auditing local file storage risks; • Helping ensure that firm data is stored in approved systems rather than only on individual devices; • Helping maintain a list of hardware, warranties, service tags, and support coverage; • Supporting rollout of endpoint setup standards across a remote team. Responsibilities Desktop and Laptop Setup Support • Assist with planning and documenting setup for Windows desktops and laptops. • Help create checklists for new computer deployment. • Verify that required software is installed and configured. • Confirm that Microsoft 365, Outlook, OneDrive, SharePoint, NetDocuments, ClickUp, Zoom, and other SaaS tools are accessible. • Help document display, keyboard, mouse, webcam, microphone, headset, printer/scanner, Ethernet, Wi-Fi, Bluetooth, and hotspot configurations. • Support testing of three-monitor workstation setups. • Help confirm that Windows display arrangements survive restart, sleep/wake, and normal daily use. SaaS and Cloud Workflow Configuration • Help document how firm software should be accessed and configured. • Support browser profile setup and SaaS bookmark organization. • Help distinguish which systems are the source of record for different types of work: o NetDocuments for client legal work product; o OneDrive for personal business working files; o SharePoint for shared operational files; o ClickUp for tasks, assignments, and workflows; o Outlook / Microsoft 365 for email, calendar, and contacts. • Help identify and reduce local-only file storage risks. Microsoft 365 / Windows Support Coordination • Support implementation of Windows 11 Pro user setup. • Help document Microsoft 365 application configuration. • Help verify OneDrive sync and Known Folder backup settings where appropriate. • Help document SharePoint library access and selective sync. • Help verify that BitLocker, MFA, endpoint protection, and update policies are in place, subject to the direction of the firm’s authorized IT administrator. • Do not independently modify tenant-level security settings unless specifically authorized. Documentation and Standardization • Create clear checklists, SOPs, and setup guides. • Document hardware standards for future purchases. • Maintain a standard software setup list by role. • Track service tags, warranty information, ProSupport coverage, and device ownership details. • Help prepare “definition of done” checklists for each setup. • Create simple end-user guides for attorneys and staff. • Document common troubleshooting steps. Coordination • Coordinate with internal team members and the firm’s existing IT vendor. • Track tasks in ClickUp. • Provide concise updates. • Escalate issues when administrative rights, vendor intervention, or security decisions are required. • Avoid making unsupported changes without approval. Required Qualifications • Experience providing Windows desktop or laptop support. • Familiarity with Windows 11 Pro. • Familiarity with Microsoft 365, Outlook, OneDrive, and SharePoint. • Ability to troubleshoot basic hardware, software, display, network, and peripheral issues. • Ability to write clear setup documentation and checklists. • Strong attention to detail. • Strong written English. • Reliable availability during agreed Pacific Time hours. • Comfortable working through Zoom, Zoom Chat, ClickUp, and remote support workflows. • Able to follow security and confidentiality requirements. • Comfortable asking clarifying questions when requirements are unclear. • Able to work independently while respecting escalation boundaries. Preferred Qualifications • Experience supporting remote professional services teams. • Experience with law firms, accounting firms, consulting firms, or other document-heavy businesses. • Experience with Dell business desktops or laptops. • Experience with Microsoft Surface laptops. • Experience with NetDocuments or another document management system. • Experience with ClickUp. • Experience with Microsoft Intune, Entra ID, Defender, BitLocker, or endpoint management. • Experience documenting SOPs for IT support. • Experience supporting multi-monitor workstation setups. • Experience working with SaaS-heavy environments. • Experience coordinating with a third-party IT vendor or managed service provider. Work Structure and Expectations This is a remote, part-time role of approximately 20 hours per week. The selected candidate must be available for scheduled overlap during 7:00 AM – 2:00 PM Pacific Time. Some work may be done flexibly outside those hours, but responsiveness during scheduled sync windows is required. The candidate will work through Upwork using hourly time tracking. Accurate time logging, work diary entries, and activity tracking are required. The candidate will communicate through Zoom, Zoom Chat, and ClickUp. We do not use Slack for this role. Communication Standards We expect clear, concise, and proactive communication. The candidate should: • Provide regular status updates; • Identify blockers early; • Document assumptions; • Ask precise questions; • Avoid silent delays; • Escalate security or administrative issues; • Keep implementation work organized in ClickUp; • Confirm completion against checklists rather than simply saying something is “done.” Confidentiality and Security This role may involve access to sensitive firm systems, internal business information, and potentially client-related technology environments. The candidate must agree that they will not: • Disclose firm or client information; • Retain copies of firm or client materials; • Use firm information for personal purposes; • Share credentials; • Store firm information in unauthorized systems; • Publish, distribute, or discuss firm information externally; • Make tenant-level, security, or administrative changes without authorization. All work product created for the firm belongs to the firm. The candidate must follow firm-approved security practices and use only approved systems. AI Usage Expectations The firm uses AI tools in its business, but AI use must be careful, confidential, and verified. The candidate may use AI tools only if permitted for the specific task and only in compliance with confidentiality rules. Any AI-assisted documentation, checklist, SOP, or recommendation must be reviewed and verified before being relied upon. The candidate may not place confidential firm or client information into unauthorized AI tools. Role Boundaries This is not a senior IT administrator role. The candidate will not be expected to independently control the firm’s Microsoft tenant, security architecture, endpoint management policies, or vendor relationships. The candidate’s role is to support, document, coordinate, test, and help standardize IT setup processes under the direction of authorized firm leadership and/or the firm’s IT vendor. The candidate should escalate issues that require: • Microsoft tenant administration; • security policy changes; • endpoint management changes; • user permission changes; • vendor-level access; • legal or compliance judgment; • purchase decisions; • credential or password resets requiring administrator approval. What We Are Not Looking For We are not looking for someone who: • Gives vague technical advice without documentation; • Says “done” without testing; • Makes unauthorized changes; • Ignores security risks; • Treats local computer storage as the main filing system; • Cannot work inside a structured task-management system; • Needs constant supervision for basic checklist-driven work; • Is careless with details; • Is uncomfortable documenting processes; • Overstates their technical abilities; • Wants to redesign the entire IT environment without first understanding current systems. Candidate Fit This role is a strong fit for someone who enjoys: • Desktop support; • Windows configuration; • Microsoft 365; • SaaS tools; • remote support; • documentation; • checklists; • process improvement; • helping non-technical professionals work more efficiently; • making technology feel simple and reliable for end users. The right candidate will be organized, patient, precise, and practical. Rose Law Firm Core Values The candidate should be able to work in a way that reflects the firm’s core values: Integrity Handle systems, credentials, documentation, and confidential information responsibly. Excellence Complete work carefully, test thoroughly, and document clearly. Coachability Accept feedback, learn our systems, and improve over time. Ownership Follow through on details, identify gaps, and help solve problems rather than merely reporting them. Teamwork Coordinate respectfully with attorneys, staff, leadership, and outside IT support. About Rose Law Firm Rose Law Firm is a fully remote, business-oriented law firm serving sophisticated business clients. The firm uses a distributed team model and relies heavily on cloud-based systems, structured workflows, Microsoft 365, document management, project management, and secure remote collaboration. We are building more scalable internal systems and are looking for team members who can help us create repeatable, professional infrastructure rather than ad hoc fixes. Long-Term Opportunity This role may grow over time for the right candidate. Possible growth areas include: • broader endpoint setup support; • recurring IT documentation; • device inventory tracking; • SaaS access audits; • onboarding and offboarding checklists; • workstation standardization; • support for attorneys and staff; • coordination with IT vendors; • support for related business operations. Performance-based advancement may be available for a candidate who demonstrates reliability, judgment, documentation skill, and careful execution. Application Requirements To apply, please provide: 1. A brief summary of your Windows desktop support experience. 2. Your experience with Microsoft 365, OneDrive, SharePoint, and Outlook. 3. Any experience with Dell business desktops, Surface laptops, or multi-monitor workstations. 4. Any experience documenting IT setup processes or SOPs. 5. Your availability during 7:00 AM – 2:00 PM Pacific Time. 6. Confirmation that you are comfortable using Upwork hourly tracking. 7. Confirmation that you can work approximately 20 hours per week. 8. Your internet reliability and backup internet plan. Required Work Sample Please respond to the following scenario: We are setting up a new Windows 11 Pro desktop for a law firm owner. The desktop will have three external monitors, Microsoft 365, Outlook, OneDrive, SharePoint, NetDocuments, ClickUp, Zoom, PDF software, Ethernet, Wi-Fi, Bluetooth, and phone hotspot backup. Please provide a short checklist of the steps you would take to make sure this computer is properly configured, secure, documented, and ready for daily use. Your answer does not need to be long, but it should be specific, organized, and practical.