Executive Assistant & Head of EA Program

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 deci