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
Work type: remote
Location: New York, New York, United States
Salary: $200,000 – $250,000/yr
Type: Full-time
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.
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.
1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.
Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.This is not a traditional EA role.
You'll be a force multiplier to the COO of a category-defining healthcare company — and the architect of how executive support works across the entire organization. In a year, you won't just be running the COO's calendar. You'll have built the function that makes Headway's leadership team operate at its best.
The Role
We're hiring an Executive Assistant / Head of EA Program to partner directly with Rob Sadow, our Chief Operating Officer, in a high-impact, high-visibility role. You'll own Rob's calendar, commitments, and operating rhythm — ensuring his time and energy are consistently focused on the highest-leverage priorities across a portfolio that spans CX, Operations, Legal, Compliance, Accounting, Finance, and the Executive Team.
But this role goes beyond supporting one executive. Headway is scaling rapidly, and we need someone to define what world-class executive support looks like here — setting the standard, building the team, and ensuring every senior leader at Headway gets exceptional EA support.
What You'll Own
COO Time, Energy & Focus (70%)
The expected base pay range for this position is $200,000 - $250,000, based on a variety of factors including qualifications and experience. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.