Headway Senior Executive Assistant to the CPO & CTO at Headway supporting R&D leadership. Manage calendars, executive operations, and meeting preparation for two executives.
Responsibilities
The Senior 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.
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.
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.
