Executive Assistant & Head of EA Program

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%) 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) EA Program Team (30%) 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 You'd be a great fit if... You are based in the NY area and are excited to be in the office 3-4 days / week 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 arou ... (truncated, view full listing at source)