Senior IT Support Technician - Flexible Scheduling

We're an early-stage startup building an exciting new IT support platform for small businesses. We’re looking for experienced IT support professionals who care as much about how they interact with people as what they fix. We're looking for independent, critical thinkers, so please do not waste either your or my time with a reply that is LLM-generated. It will be immediately discarded without further consideration. The Role You’ll work as an independent contractor, accepting support jobs through our in-house dispatching system. You'll effectively set your own hours, accepting only those jobs that work with your schedule. Initially, support may involve more direct customer interaction (live sessions, screen sharing), with the expectation that over time, more issues may become asynchronous as our software matures. This is a startup, so details will evolve as we learn. We’re upfront about that and value technicians who can work comfortably in a system that’s improving in real time. ⸻ What You’ll Help With (Examples) Typical issues include the kinds of problems MSP technicians see every day, such as: • Microsoft 365 issues (Outlook, OneDrive sync, licensing, account access) • Wi-Fi or basic network troubleshooting • Printer setup and connectivity issues • Performance issues, disk space cleanup, basic security concerns • Helping non-technical users understand what’s going on and what to do next Technical competence matters, but calm, clear, human communication matters even more, especially early on. ⸻ What We’re Looking For Required • 3–5+ years of IT support / helpdesk experience (MSP experience strongly preferred) • Excellent people skills: patient, clear, and comfortable interacting directly with end users • Strong written and spoken communication • Ability to explain your troubleshooting approach step-by-step • Good listener; customers shouldn’t need to repeat themselves • Reliable and punctual when you accept a support session • Comfortable following structured support flows and documenting outcomes • US-based with native-level English fluency Strongly Preferred • Willingness to offer candid, constructive feedback to improve our processes • Interest in contributing to troubleshooting documentation (what worked, what didn’t) • Located in or near Austin or NYC (optional; may enable on-site work in the future) ⸻ Flexibility, Pay & Structure • Contractor role • You choose when to accept jobs • Compensation will start hourly while we establish baselines and gather data No guaranteed hours initially, so this opportunity is best suited for experienced technicians who may already have a roster of their own clients and are looking for interesting, additional work. ⸻ Trial Process (Paid) Shortlisted candidates will complete a paid live trial: • A realistic support scenario • Live interaction and troubleshooting • Focused on communication, judgment, and problem-solving, not speed or memorization This helps ensure a good mutual fit before ongoing work. ⸻ Who This Is Not For • Entry-level or script-only support roles • High-volume, low-touch ticket grinding • Technicians who dislike customer interaction or documentation • Anyone uncomfortable with evolving systems in an early-stage product To confirm you read the full post, please include the phrase “clear communication” somewhere in your application. ⸻ How to Apply Please include: 1. A brief summary of your IT support experience (especially MSP work) 2. One example of a support issue where communication with the user mattered as much as the fix 3. Your typical availability (roughly) 4. (Optional) What you think most IT support systems get wrong today