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.
1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.
But we're going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. 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.