Executive Assistant to the CPO & CTO

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 take ownership instinctively - you see what needs to happen, step into gaps, and stay with problems through resolution.

• You exercise independent judgment without overstepping — and know when to act, ask, escalate, or push back.

• You learn your executives quickly — how they think, work, and prioritize — and adapt your support without needing every preference or next step spelled out.

• You build business and R&D context quickly and use it to make better decisions, not just become more informed.

• You enjoy supporting large, fast-moving teams — from complex calendars and leadership rhythms to offsites, events, and the details that make an organization run smoothly.

• You measure success by Jake and Arnaud’s effectiveness, not tasks completed — and are comfortable challenging an initial ask when you believe a different approach will produce a better outcome.

Compensation & Benefits

Comprehensive total rewards package including equity, health/wellness benefits, and retirement savings.

Benefits include: Equity Compensation (RSUs) · Medical, Dental, Vision · HSA/FSA · 401K · Work-from-Home Stipend · Therapy Reimbursement · 16-week parental leave · Carrot Fertility · 13 paid holidays + Holiday Break (Dec 25–31) · Flexible PTO · EAP · Training and professional development