Executive Assistant & Head of EA Program

Headway•New York, NY

12h•$200,000 - $250,000•Hybrid

About The Position

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.

Requirements

You are based in the NY area and able to come into the office in a hybrid capacity
You have 8+ years of experience supporting C-suite executives at high-growth technology companies — and you genuinely love being an EA. This isn't a stepping stone; it's the career you've chosen and you want to be exceptional at it
You have experience managing other EAs — hiring, coaching, giving direct feedback, and building a team culture of excellence
You manage your executive, not the other way around — you're comfortable being vocal, direct, and decisive with a senior leader, and you make independent judgment calls and see three steps ahead
Your written and verbal communication is flawless — grammar, punctuation, tone, and clarity are non-negotiable. You represent your executive in every interaction
You build strong relationships cross-functionally — other leaders and EAs trust you, enjoy working with you, and see you as someone who makes things easier, not harder
You thrive in fast-paced, high-standards environments — Headway operates at an Olympic performance standard, and you're energized by that, not intimidated
You are excited by our mission to rewire mental healthcare for access and affordability

Responsibilities

Own the COO's calendar end-to-end — not just scheduling, but making hard prioritization decisions about what gets Rob's time and what doesn't
Design schedules for deep work, energy, and presence — not just efficiency
Prep Rob for every meeting with full context on attendees, purpose, relevant documents, and key decisions needed — he should never walk into a meeting cold
Own travel logistics end-to-end, including events and personal travel
Manage key relationships on Rob's behalf — knowing who to prioritize, who to push, and when to escalate
Track action items and commitments across Rob's portfolio so nothing falls through the cracks
Support personal and family logistics where relevant — including protecting boundaries that matter (like being offline for family time in the evenings)
Define what exceptional EA performance looks like at Headway — set the operating model, tools, rituals, and standards for the function
Hire, manage, and coach EAs supporting the CEO and other executives
Own performance management, career development, and onboarding for the EA team
Build an EA-specific leveling framework and ensure compensation, expectations, and growth paths are clear and competitive

Benefits

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development