Executive Assistant to the CPO & CTO

Headway•New York, NY

3d•$143,200 - $179,000•Remote

About The Position

Headway is a Series D company with over $325M in funding, aiming to fix the mental healthcare system by making it accessible to everyone. They have automated the administrative work involved in insurance for mental health providers, and over 75,000 providers use their software. The company is building tools for therapists, improving the experience of finding a therapist, and investing in platform foundations to scale their services. This role of Executive Assistant to the Chief Product Officer and Chief Technology Officer is a high-leverage position within the R&D organization, focused on maximizing the effectiveness of these two executives. The EA will partner closely with the CPO and CTO to ensure their time and preparation are focused on critical areas. This role goes beyond traditional executive support, requiring anticipation of needs, building structure, exercising sound judgment, and owning tasks through resolution. The EA will deeply learn the executives' operating styles to provide tailored support and create leverage. Working with the R&D Chief of Staff, the EA will help create a seamless operating environment for R&D leadership, with success measured by the executives' effectiveness and focus on high-impact work.

Requirements

Takes ownership instinctively and sees problems through to resolution.
Exercises independent judgment and knows when to act, ask, escalate, or push back.
Quickly learns executives' thinking, working styles, and priorities to adapt support.
Builds business and R&D context rapidly to make informed decisions.
Enjoys supporting large, fast-moving teams with complex calendars, leadership rhythms, offsites, and events.
Measures success by executive effectiveness rather than tasks completed.
Comfortable challenging initial asks when a different approach might yield better outcomes.

Responsibilities

Own Jake and Arnaud's calendars end-to-end, aligning time to high-priority work, protecting focus and preparation, filtering requests, and navigating competing demands.
Build systems for executive operations, including priorities, tasks, follow-up, information flow, travel, and logistics, tailored to each executive's working style.
Ensure executives are prepared for important meetings by coordinating context and materials, engaging stakeholders, protecting preparation time, and anticipating needs.
Support the operating needs of large, fast-growing organizations by planning leadership and team offsites, coordinating events, and managing logistics for Product and Engineering.
Manage communication across email, Slack, and with key stakeholders, ensuring information reaches the right place, commitments are tracked, and loops are closed.
Act as connective tissue by deeply learning executive operating styles, anticipating support needs, exercising independent judgment, and taking ownership without explicit direction.