Executive Assistant to the CPO & CTO at Headway in New York, NY

Job description

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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, Spark Capital, 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. About the Role The Executive Assistant to the Chief Product Officer and Chief Technology Officer is a high-leverage role at the center of Headway’s R&D organization. This role will partner closely with Jake Poses, Chief Product Officer, and Arnaud Ferreri, Chief Technology Officer, to maximize their effectiveness — ensuring their time, attention, and preparation are focused on the product, technology, people, and decisions that matter most. The role extends well beyond traditional executive support. A great Executive Assistant anticipates what’s needed, builds structure where it’s missing, exercises sound judgment, and owns work through resolution. They deeply learn how each executive operates and translate that understanding into tailored support - creating leverage without requiring every need or next step to be explicitly defined. Working closely with Jake, Arnaud, and the R&D Chief of Staff, this person will help create a seamless operating environment around R&D leadership. Ultimately, success is measured by outcomes, not tasks: Jake and Arnaud are focused on their highest-impact work, consistently prepared for important moments, and supported by an EA whose effectiveness and ownership compound as their context and trust deepen. What You'll Own • Time & Calendar | You'll own Jake and Arnaud's calendars end-to-end — aligning time to their highest-priority work, protecting focus and preparation, filtering and reshaping requests, and navigating competing demands across two executives. • Executive Operations | You'll build the systems that keep both executives running effectively - across priorities, tasks, follow-up, information flow, travel, and day-to-day logistics - tailored to how each works and continuously improved as you learn them. • Meeting Preparation | You'll ensure Jake and Arnaud are prepared for the moments that matter - coordinating context and materials, engaging the right stakeholders early, protecting preparation time, and anticipating what they need before they walk into the room. • Team & R&D Operations | You'll support the operating needs of two large, fast-growing organizations — planning leadership and team offsites, coordinating events and key team moments, and owning the logistics that enable Product and Engineering to operate effectively. • Communications & Follow-Through | You'll help manage communication and coordination across email, Slack, and key stakeholders - ensuring important information gets to the right place, commitments are tracked, and loops are reliably closed. • Executive Partnership | The connective tissue across all of the above. You'll deeply learn how Jake and Arnaud each operate, anticipate where support is needed, exercise independent judgment, and take ownership without waiting for every next step to be defined You'd Be a Great Fit If… • You t