IT Support Specialist - Contractor

Flex is a growth-stage, NYC-headquartered FinTech company creating the best rent payment experience. We enable users to pay rent throughout the month on a schedule that fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense.

About the role

Flex is seeking IT Support contractors to serve as the front line for tier 1 & 2 IT requests for our Customer Success organization. This contract role focuses on hands-on execution against documented procedures, with an emphasis on account provisioning, access management, and rapid troubleshooting. The role sits within the IT function, reports to the IT Manager, and works closely with the CS Tools & Technology team on tool-level escalations and cross-functional workflows.

The ideal candidate is a strong technical generalist with a service-delivery mindset, comfortable working in a high-volume ticket environment, and disciplined about executing sensitive access changes accurately.

Engagement Details: Contract (W2), initial 6-month engagement with possibility of extension. 30+ hours/week during standard business hours (ET). In-office at Flex HQ (NYC) 4 out of 5 days. Reports to IT Manager.

Responsibilities

• Own tier 1 & 2 IT support for the CS organization: account provisioning, access upgrades, password resets, MFA and SSO issues, and general troubleshooting. Resolve directly or escalate 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 account creation, group membership, permission changes, and license assignment.
• Partner with the CS Tools & Technology team on Zendesk, Amazon Connect, and CSAT tool issues requiring 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, ensuring consistency as request volume scales.
• Escalate cleanly on issues outside documented scope, and flag documentation gaps or recurring pain points to the IT Manager.

Requirements

• 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.
• Working knowledge of macOS (primary), Windows, iOS, and Android in a business environment.
• Experience with Google Workspace administration at the user level (account management, group membership, drive sharing).
• Comfort working in ticketing platforms (Jira Service Management preferred; Zendesk experience a plus) and adhering to defined SLAs.
• Strong attention to detail and process discipline. This role handles sensitive access changes that need to be done right the first time.
• Comfortable working directly with a technical IT team and translating between end-user, CS, and IT contexts.
• Strong written communication for chat and ticket-based support; ability to translate technical issues into plain language.
• Ability to work independently against documented procedures and escalate appropriately when unclear.
• AI-forward mindset; comfortable using AI tools to work faster on drafting, summarization, and routine configuration while verifying accuracy against SOPs and system data.

Nice-to-Haves

• 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.

Pay

Pay range is $40–$50 USD per hour for candidates located in Tier 1 (NYC/Bay Area) markets. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside these areas, your starting pay will be adjusted to align with the market conditions of your specific geographic zone.

Benefits

For full-time U.S. employees:

• Competitive medical, dental, and vision
• Company equity
• 401(k) plan with company match
• Unlimited paid time off + 13 company paid holidays
• Parental leave
• Free Flex subscription

For full-time non-U.S. employees:

• Competitive compensation + company equity
• Unlimited PTO