Strategic EA to CPO & CTO — R&D Ops

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

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.