Executive Assistant to the CPO & CTO

Join Headway as an Executive Assistant to the Chief Product Officer and Chief Technology Officer. In this high-leverage role, you will partner closely with the executives to maximize their effectiveness and create a seamless operating environment around R&D leadership. Your responsibilities will include managing their calendars, building systems for effective operations, preparing for important meetings, supporting team and R&D operations, managing communications, and exercising independent judgment. Success will be measured by the effectiveness of the executives, not just tasks completed.

• Assurer la gestion complète des calendriers de Jake et Arnaud, en alignant leur temps sur leurs travaux prioritaires.
• Construire et améliorer les systèmes qui permettent aux deux dirigeants de fonctionner efficacement, en adaptant les priorités, les tâches et les suivis.
• Préparer Jake et Arnaud pour les moments importants en coordonnant le contexte et les matériaux, en engageant les bonnes parties prenantes.

• You take ownership instinctively - you see what needs to happen, step into gaps, and stay with problems through resolution
• 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 build business and R&D context quickly and use it to make better decisions, not just become more informed
• 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 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
• You exercise independent judgment without overstepping — and know when to act, ask, escalate, or push back