IT Support Technician (Contractor)

Overview 

UPSTACK is the leading full-service technology advisory firm, transforming how businesses design, source, implement, support, and optimize IT infrastructure. Clients benefit from decades of expertise, enhanced support, and UPSTACK’s proprietary technology—delivering faster deployments, cost savings, and streamlined access to critical solutions.

Our expertise includes: data center colocation, network connectivity, SD-WAN, unified communications, cloud contact center, CX-AI, private/public cloud, security, mobility, business continuity, and IoT.

Under the leadership of Founder and CEO Christopher Trapp, UPSTACK is committed to exceptional customer experiences, serving 6,500+ clients—from SMBs to enterprises—and managing over $550M in annual technology spend across industries.

About the Role

We’re looking for a full-time IT Support Technician (Contractor) to join our distributed technology team. In this critical role, you will provide high-quality, proactive technical support to end-users and executives across the organization. Your mission is to ensure seamless day-to-day operations in a remote-first environment through your technical expertise, customer service mindset, and problem-solving abilities. You’ll play a key part in maintaining productivity by troubleshooting issues, managing devices, and implementing IT best practices across our systems.

Key Responsibilties

• Provide first and second-line remote IT support for end-users and executives, troubleshooting hardware, software, and network issues. 
• Manage user accounts and access permissions using Okta and M365, including onboarding and offboarding processes. 
• Administer and support Apple and Windows devices through JAMF and Intune, including deployment, configuration, and ongoing management. 
• Respond to, document, and resolve support tickets via our IT service desk platform, ensuring timely and effective solutions. 
• Deliver white glove support to executives and leadership, understanding the unique requirements and urgency of executive IT needs. 
• Assist in the rollout of updates, patches, and security enhancements across all managed devices and software platforms. 
• Maintain up to date documentation for IT procedures, user guides, and knowledge base articles. 
• Monitor system alerts and proactively address issues in a remote environment. 
• Manage multiple requests, tasks, and projects simultaneously, prioritizing workload according to business impact and deadlines. 
• Collaborate with cross functional teams to support new technology initiatives and continuous improvement of IT services. 

Required Qualifications

• Proven experience in remote IT support, with a strong track record supporting distributed teams. 
• Hands on expertise with Okta, M365 (Exchange Online, Teams, SharePoint, OneDrive, etc.), JAMF, and Intune for device and identity management. 
• Demonstrated ability to support both MacOS and Windows environments. 
• Exceptional troubleshooting and analytical skills for both hardware and software issues. 
• Experience providing high-level support to executives, including discretion, professionalism, and responsiveness. 
• Strong multitasking and time management abilities; adept at handling competing priorities in a fast-paced setting. 
• Excellent verbal and written communication skills; ability to translate technical concepts for non-technical users. 
• Familiarity with ticketing systems, remote assistance tools, and knowledge base maintenance. 
• Experience with security applications such as SentinelOne, Zscaler, Microsoft Defender, and Abnormal Security is helpful. 

Tool Proficiency

Must Know:

• Support the following tech stack
  • Okta
  • M365
  • Zoom
  • Atlassian (Jira) 
• Supported MacOS and Windows in a remote-first environment.
• MDM administration experience (e.g., JAMF, Intune). 
• Helpdesk ticketing system experience 
• Strong understanding of IT security protocols and standards
• Proficiency in implementing and adhering to IT security frameworks

Nice to know: 

• Zscaler 
• SentinelOne 
• Abnormal Security 
• Microsoft Defender 
• RMM Tools (NinjaOne or something similar) 
• Scripting experience (Bash or PowerShell) 

Contract Details

• Position Type: Full-time (40 hours/week)

• Employment Type: W9 Contractor

• Contract Duration:  Ongoing

• Target Start Date: August 1, 2025 (or sooner)

• Interview Process: 1 phone/ 3 video interviews

• Application Requirement: Please include your monthly rate when applying

We’re moving quickly and looking to make a decision soon—if this sounds like the right fit, we’d love to hear from you.

Interview Process

• 30-minute phone screen to discuss your background, experience, and interest in the role
• 60-minute technical interview with the IT Admin
• 60-minute interview with the Director of IT
• 30-minute conversation with the SVP, Product & Technology

Closing

UPSTACK is an Equal Opportunity Employer and does not discriminate based on race, gender, ethnicity, religion, national origin, age, disability, veteran status, gender identity/expression, sexual orientation, or on any other basis prohibited by law. Consistent with applicable state and local law, UPSTACK will consider employment for all qualified applicants.

UPSTACK is committed to providing reasonable accommodations to individuals with disabilities as required by applicable law. Accommodations may include adjustments to the application, interview, or assessment process, as well as modifications to the work environment or job duties to enable individuals to perform the essential functions of the role. Requests for accommodations will be evaluated on a case-by-case basis and provided unless they impose an undue hardship on the organization.

At this time, UPSTACK will not sponsor a new applicant for employment authorization for this position.

We endeavor to make the application process accessible to all applicants. If you would like to contact us regarding accessibility and/or need assistance completing the application process, please contact us at recruiting@upstack.com.