Sr. Help Desk Technician

About Curative Curative is building the future of health insurance with a first-of-its-kind employer-based plan designed to remove financial barriers and make care truly accessible: one monthly premium with $0 copays and $0 deductibles*. Backed by our recent $150M in Series B funding and valuation at $1.275B , Curative is scaling rapidly and investing in AI-powered service, deeper member engagement, and a smart network designed for today’s workforce. Our north star guides everything we do: healthcare only works when people can actually use it . That belief drives every decision we make: from how we design our plan, support our members, to how we collaborate as a team. If you want to do meaningful work with a team that moves fast, experiments boldly, and cares deeply, Curative is the place to do it. We’re growing fast and looking for teammates who want to help transform health insurance for the better. Position Summary We are seeking a Senior Help Desk Technician with strong operational and automation experience to help scale and modernize IT support services. This role is designed for a highly capable technician who can both resolve complex support issues and build sustainable systems (including Agentic AI-powered workflows) that reduce manual effort across the help desk function. The ideal candidate has approximately 4+ years of progressive IT support experience, including hands-on ownership of help desk tooling, workflow automation, knowledge management, endpoint administration, and service process optimization. This individual will help transform support operations from reactive ticket handling into scalable, automation-driven service delivery. This is a highly technical, process-oriented role focused on improving operational efficiency, reducing repetitive work, and enabling the broader IT organization to scale effectively. Key Responsibilities: Occasional Tier 1 support, especially to understand opportunities for automation. Provide Tier 2/Tier 3 support for complex hardware, software, endpoint, identity, and SaaS-related issues. Build, maintain, and improve internal AI-driven support tools and automation systems, including monitoring performance, updating workflows, and helping optimize end-user support experiences. Troubleshoot and support Windows and macOS operating systems in a business environment. Support collaboration, productivity, and cloud-based business applications. Serve as an escalation point for unresolved support requests and critical incidents. Identify repetitive support tasks and implement workflow improvements and automation, including AI agents, to reduce manual effort. Improve onboarding, offboarding, provisioning, ticket routing, and knowledge management processes. Assist with developing scalable self-service and support solutions. Contribute to operational documentation, process standardization, and service improvement initiatives. Utilize ticketing and IT service management platforms to manage support requests, escalations, and workflow tracking. Ensure accurate ticket documentation, prioritization, escalation, and resolution tracking. Assist with SLA management, service reporting, and operational metrics. Analyze recurring issues and recommend long-term improvements to reduce support volume and increase efficiency. Mentor junior technicians and contribute to overall team development. Collaborate with infrastructure, security, and engineering teams to improve operational workflows and end-user experience. Deliver exceptional customer service while communicating technical concepts clearly to non-technical users. Qualifications & Experience: Minimum of 4 years in IT support, help desk, or desktop support roles. Experience supporting both Windows and macOS environments in a business setting. Experience working within structured help desk or IT operations environments. Hands-on experience improving operational workflows, service processes, or support efficiency initiatives. Experience with Google Workspace and Microsoft Entra administration. Technical Skills: Proficiency supporting cloud-based productivity and collaboration platforms. Experience with endpoint management and device administration tools. Experience with user provisioning and lifecycle management processes. Strong troubleshooting experience across hardware, software, networking, and SaaS applications. Experience with AI-enabled support tools, n8n workflows, Google Apps Script, Slack integrations, Jira automation, Claude Code, and Github (or similar systems). ITSM & Operations: Familiarity with ITSM frameworks and IT service best practices. Experience contributing to workflow automation, service improvements, or operational scaling initiatives. Strong understanding of support documentation and knowledge management practices. Communication & Problem-Solving: Strong verbal and written communication skills. Excellent organizational and interpersonal skills. Strong analytical and troubleshooting abilities with a proactive approach to issue resolution. Ability to prioritize tasks and manage multiple requests in a fast-paced environment. Education: Bachelor’s degree in Information Technology, Computer Science, or a related field, or equivalent professional experience. What We Offer: Competitive salary and benefits package. Opportunities for professional development and career growth. A collaborative and inclusive work environment. If you are a proactive and innovative thinker who thrives in a fast-paced environment, we would love to hear from you! Please submit your resume and a cover letter detailing your relevant experience. Perks & Benefits Curative Health Plan (100% employer-covered medical premiums for you and 50% coverage for dependents on the base plan.) $0 copays and $0 deductibles (with completion of our Baseline Visit ) Preventive and primary care built in Mental health support (Rula, Televero, Two Chairs, Recovery Unplugged) One-on-one care navigation Chronic condition programs (diabetes, weight, hypertension) Maternity and family planning support 24/7/365 Curative Telehealth Pharmacy benefits Comprehensive dental and vision coverage Employer-provided life and disability coverage with additional supplemental options Flexible spending accounts Flexible work options: remote and in-person opportunities Generous PTO policy plus 11 paid annual company holidays 401K for full-time employees Generous Up to 8–12 weeks paid parental leave, based on role eligibility.