IT Support Specialist (Contractor)

• Flex is in search for IT Support contractors to serve as the front line for tier 1 & 2 IT requests for our Customer Success organization
• This is a contract role that will have hands-on execution against documented procedures, with an emphasis on account provisioning, access management, and rapid troubleshooting
• The role sits within the IT function and reports to the IT Manager, and works in close partnership with the CS Tools & Technology team on tool-level escalations and cross-functional workflows
• Own tier 1 & 2 IT support for the CS organization: account provisioning, access upgrades, password resets, MFA and SSO issues, and general troubleshooting. Resolving directly or escalating with clean context to senior IT staff
• Execute CS agent onboarding and offboarding against established runbooks, including account creation, group and role assignments, hardware and tooling access, and clean deprovisioning on separation
• Serve as the day-to-day IT point of contact for the CS org, keeping account and access requests moving without needing manager involvement
• Support CS IT help desk requests via Slack, Zoom, phone, and in-person on hardware, software, account, and connectivity issues
• Handle user-level administration for Google Workspace, Slack, Jira, and Confluence. Including but not limited to account creation, group membership, permission changes, and license assignment
• Partner with the CS Tools & Technology team on Zendesk, Amazon Connect, and CSAT tool issues that require IT-side access or account intervention, escalating tool configuration work to their team
• Triage and resolve tickets, keep the queue clean, and meet defined SLAs
• Identify recurring, repetitive requests (onboarding, access changes, common resets) and propose lightweight automations using tools like Zapier or Superblocks to reduce manual handling
• Document and maintain SOPs and runbooks in Notion for IT support processes affecting BPO and CS, so the process stays consistent as request volume scales
• Escalate cleanly on issues outside documented scope, and flag documentation gaps or recurring pain points to the IT Manager
• Reports to: IT Manager
• Partners with: CS Tools & Technology team on tool-adjacent work
• Type: Contract (W2)
• Duration: Initial engagement of 6 months with possibility of extension based on business need and performance
• Hours: 30+/week during standard business hours (ET)

Benefits

• Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
• Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
• NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
• 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
• Flex Giving: ‍Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
• Employee Assistance Fund: ‍Confidential financial support to teammates facing unexpected hardships or emergencies.
• Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter.
• Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
• Free Flex Subscription: As a Flex employee, you’ll have full access to our services without charge.
• GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead.- The ideal candidate is a strong technical generalist with a service-delivery mindset, comfortable working in a high-volume ticket environment, and disciplined about doing sensitive access changes right the first time
• Comfort working in ticketing platforms (Jira Service Management preferred; Zendesk experience a plus) and adhering to defined SLAs
• Strong written communication for chat and ticket-based support; ability to translate technical issues into plain language
• 1–3 years in an IT support, help desk, or technical CS/support operations role
• Hands-on experience with account provisioning and access management: onboarding, offboarding, password resets, and permission changes
• AI-forward mindset; comfortable using AI tools to work faster on drafting, summarization, and routine configuration while verifying accuracy against SOPs and system data
• Strong attention to detail and process discipline. This role handles sensitive access changes that need to be done right the first time
• Ability to work independently against documented procedures and escalate appropriately when unclear
• Experience with Google Workspace administration at the user level (account management, group membership, drive sharing)
• Working knowledge of macOS (primary), Windows, iOS, and Android in a business environment
• Comfortable working directly with a technical IT team and translating between end-user, CS, and IT contexts
• Prior experience supporting a vendor-agent environment at scale
• Experience with Google Workspace, Slack, or Zendesk at the user administration level
• Familiarity with SSO/SCIM concepts (Okta, Google as IdP) at the end-user provisioning level
• Hands-on experience with Zapier, Superblocks, or similar workflow automation tools
• Familiarity with an MDM platform (Hexnode, Kaseya, Jamf, Intune, or similar)
• Exposure to UniFi or comparable network hardware for basic Wi-Fi troubleshooting
• CompTIA A+, Network+, or similar certifications