# Chief of Staff, R&D

**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** New York, NY
**Role:** Business Operations
**Salary:** $230k – $300k/yr
**Experience:** 10+ years
**Skills:** Product Development Lifecycle, Capacity Planning, Headcount Planning, Budget Governance, Roadmap Planning, Organizational Design, Technical Risk, Architecture, AI Tools, Strategy Reviews, Decision Memos, Board Materials, Data, Product Management
**Posted:** 2026-08-18

> Leads the operating system for a large R&D organization, coordinating planning, prioritization, headcount, governance, executive communications, and cross-functional alignment across Product, Engineering, Data, and Design. Requires prior executive Chief of Staff experience, 10+ years of relevant experience, strong writing, technical fluency, and influence without authority.

## Job Description

## Responsibilities
- Own the R&D rhythm of business, including leadership staff meetings, product and technology reviews, quarterly planning, R&D all-hands, and board meeting preparation.
- Run the R&D planning cycle end to end, coordinating team-level plans across Product, Engineering, and Design and establishing company-level commitments.
- Surface prioritization trade-offs with options, costs, and recommendations.
- Write board materials, strategy reviews, decision memos, and R&D-wide communications.
- Connect Product, Engineering, Data, and Design; identify misalignment early and help leaders converge on direction and next steps.
- Address high-priority, under-owned problems such as organization design, capacity and roadmap-resourcing alignment, and adapting operations to AI-enabled work.
- Partner with Finance and People on headcount planning, capacity modeling, budget governance, and senior onboarding.
- Improve escalation discipline and ensure risks reach the right leader quickly with follow-through.
- Represent R&D leadership in relevant meetings.

## Requirements
- Experience supporting a product or engineering executive as a Chief of Staff.
- 10+ years across strategy, business operations, management consulting, product management, engineering leadership, or Chief of Staff roles.
- Deep understanding of R&D organizations, including product development lifecycles, organizational structures, capacity planning, and roadmap-resourcing alignment.
- Excellent writing skills, including the ability to turn complex and contested topics into concise briefs, memos, or presentations that enable decisions.
- Technical fluency sufficient to discuss architecture, technical risk, and engineering trade-offs with senior engineers.
- Ability to influence without formal authority and build trust with peers and executives.
- Ability to structure ambiguity while maintaining speed and sound judgment.
- AI-native working practices and a clear perspective on how AI changes R&D operations.

## Nice to Have
- Experience in healthcare, marketplaces, or other multi-stakeholder businesses.
- Experience at a company scaling through 1,000 employees.

## Compensation and Benefits
- Expected base pay range: **$230,000-$300,000**.
- Equity compensation.
- Medical, dental, and vision coverage.
- HSA/FSA.
- 401(k).
- Work-from-home stipend.
- Therapy reimbursement.
- 16-week parental leave for eligible employees.
- Carrot Fertility annual reimbursement and membership.
- 13 paid holidays and a holiday break during the week between December 25 and December 31.
- Flexible PTO.
- Employee Assistance Program (EAP).
- Training and professional development.

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