Executive Assistant to the CPO & CTO

Headway.co; New York (NY); On-site; USD 110,000 - 170,000; Full time

Benefits offered by this job

Equity RSUs

Medical Insurance

Dental Insurance

Vision Insurance

HSA/FSA

401K

Work-from-Home stipend

Therapy Reimbursement

16 weeks parental leave

Carrot Fertility

13 paid holidays

Flexible PTO

EAP

Professional development

Job summary

Headway is hiring an Executive Assistant to the Chief Product Officer and Chief Technology Officer in New York. This high-leverage role partners with two top executives, ensuring their time, attention, and preparation focus on product, technology, people, and decisions that matter most.

You will build structure, anticipate needs, and own work through resolution, translating executive styles into tailored support. The role requires proactive problem-solving and a strong sense of accountability.

Qualifications

• Experience supporting C-suite executives is preferred.
• Strong written and verbal communication skills.
• Ability to build structure and anticipate needs.

Responsibilities

• Time & Calendar: manage calendars end-to-end and shield time for priority work.
• Executive Operations: create systems for two executives, handle travel and logistics.
• Meeting Preparation: coordinate context and materials for important meetings.
• Team & R&D Operations: plan leadership offsites and events, coordinate team moments.
• Communications & Follow-Through: manage email/Slack and track commitments.
• Executive Partnership: learn executives deeply and provide proactive, independent support.

Skills

Ownership mindset

Independent judgment

Executive learning

Cross-functional collaboration

Operations & logistics

Job description

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 75,000 providers across all 50 states run their practice on our software, serving over 1 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. 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 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, escal…

• 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.

Compensation & Benefits

Comprehensive total rewards package including equity, health/wellness benefits, and retirement savings.

Benefits include: Equity Compensation (RSUs) Medical, Dental, Vision HSA/FSA 401K Work-from-Home Stipend Therapy Reimbursement 16-week parental leave Carrot Fertility 13 paid holidays + Holiday Break (Dec 25–31) Flexible PTO EAP Training and professional development

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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