Executive Assistant & Head of EA Program

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%) 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 around — you're comfortable being vocal, direct, and dec