Executive Assistant & Head of EA Program at Headway

This isn’t a typical administrative role; it is a leadership position for a career Executive Assistant who wants to build a department. The ideal candidate has 8+ years of C-suite support experience in high-growth tech and genuinely loves the craft of executive partnership. You must be comfortable managing "up" to a COO while simultaneously acting as a functional lead who hires, coaches, and sets the standard for the entire EA team. The compensation is highly competitive ($200k–$250k) and includes equity at a Series D company backed by top-tier VCs like a16z and Accel. While the role is listed as remote, it requires a hybrid presence in New York City to partner effectively with leadership. Standout perks include 16 weeks of parental leave, a week-long year-end holiday break, and specialized benefits like therapy and fertility reimbursement. **You might be a good fit if you...** * See yourself as a "force multiplier" who can proactively manage a COO’s energy and priorities, not just their calendar. * Have prior experience managing other EAs and building career ladders or leveling frameworks. * Work with "Olympic-level" standards and possess flawless written communication skills. * Are based in NYC and want to combine high-level administrative work with organizational design.