IT Support Specialist - Contractor

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? 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. 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. Engagement Details: 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) Location: In-office at Flex HQ (NYC) - Required to be in office 4 out of 5 days. Reports to: IT Manager Partners with: CS Tools & Technology team on tool-adjacent work Compensation: Pay range is in USD as an hourly basis Key Responsibilities: 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. Qualifications: 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. Compensation Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location. Tier 1 (NYC/Bay Area) $40 — $50 USD Life at Flex We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace. Offices Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program. Benefits For full-time U.S. employees we offer: 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, we offer: Competitive compensation + company equity Unlimited PTO