Senior Operations Associate at Headway

This role is ideal for mid-career professionals with 3–5 years of experience in high-intensity environments like management consulting, investment banking, or high-growth startup operations. It suit "systems thinkers" who enjoy moving between high-level strategy and hands-on execution. You should be comfortable using data to drive decisions and have an interest in navigating the complexities of the US healthcare system. The position offers a fully remote environment with a competitive salary up to $112,000, plus equity—a significant perk for a Series D company backed by top-tier VCs like a16z. Standout benefits include specialized perks like therapy reimbursement, fertility support (Carrot), a work-from-home stipend, and a dedicated company-wide break between Christmas and New Year’s. **You might be a good fit if you...** * Have a background in consulting or finance and want to transition into a product-first tech environment. * Are highly data-driven and capable of performing complex analyses to find process bottlenecks. * Enjoy building automation-led solutions rather than just managing manual workflows. * Want to work at the intersection of logistics, insurance, and mental health accessibility.