Senior Executive Assistant to the CPO & CTO

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the Role

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.

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.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.