H
Executive Assistant to the CPO & CTO
Headway
Overview
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, a
Benefits, from the posting itself
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Equity Compensation (RSUs)receipt ⟳
“Equity Compensation (RSUs)”
Medical, Dental, Visionreceipt ⟳
“Medical, Dental, Vision”
HSA/FSAreceipt ⟳
“HSA/FSA”
401Kreceipt ⟳
“401K”
Work-from-Home Stipendreceipt ⟳
“Work-from-Home Stipend”
Key Responsibilities
- 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.
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