Chief of Staff, R&D

Headway • New York, NY

2d • Remote

About The Position

R&D — Engineering, Product, Design and Data — is Headway's largest investment and the engine of our growth. By early 2027 we expect to be a [500]-person R&D team, and we're rebuilding how the org works now that AI has changed what a team can do. As Chief of Staff, R&D, you own the operating system that lets this organization decide fast and stay aligned. You’ll run the operations of the R&D org from quarterly/annual planning to headcount prioritization to improving our ways of working on a continuous basis. You'll run the rhythm of the org, turn strategy into plans with named owners and real dates, surface the trade-offs that leaders need to see before they choose. You will be the connective tissue across Product, Engineering, Data, and Design, and the person who notices misalignment a month before it becomes a missed quarter. This is a Director-level individual contributor role. This is not an administrative coordinator role, and it is not a shadow VP of Product or Engineering. You won't own a roadmap or tell teams what to build. You'll own how work moves.

Requirements

• Supported a product or engineering executive (or both) as their chief of staff.
• 10+ years across strategy, business operations, management consulting, product management, engineering leadership, or prior Chief of Staff roles.
• Deep fluency in how R&D organizations actually work: the product development lifecycle, org structures, capacity planning, and the perennial gap between a roadmap and the people available to build it.
• Genuinely excellent writer. Can take a complex, contested topic and produce the brief, memo, or deck that moves a decision — and can write in someone else's voice when the moment calls for it.
• Technical enough to be credible. Don't need to write code, but need to hold your own in a conversation about architecture, technical risk, and engineering trade-offs, and earn the trust of senior engineers.
• Operate through influence rather than authority, and have built the standing to do it before — with peers who didn't report to you and executives who didn't have to listen.
• Bring structure to ambiguity without smothering speed, and have the judgment to know which of those two matters more in a given week.
• AI-native in how you work — have rebuilt your own workflows around these tools and have a real point of view on what they change about how an R&D org should operate.

Nice To Haves

• Healthcare, marketplace, or other multi-stakeholder business experience
• Time inside a company scaling through 1,000 people

Responsibilities

• Own the R&D rhythm of business: leadership staff meetings, product & tech reviews, quarterly planning, R&D all-hands, board meeting prep etc. Build the minimum process each one needs and no more.
• Run the R&D planning cycle end to end — draft the guidance, coordinate team-level plans across Product, Engineering, and Design, and land a set of commitments the company can hold us to.
• Surface trade-offs rather than resolve them quietly. Bring leaders options, costs, and a recommendation so that prioritization calls are explicit and visible.
• Write for the leadership team: board materials, strategy reviews, decision memos, and R&D-wide communications. Turn a messy debate into two pages that make the decision obvious.
• Act as connective tissue across the org, spot misalignment early and help leaders converge on direction, trade-offs, and next steps.
• Take on the highest-priority, least-owned problems: org design, capacity and roadmap-resourcing alignment, how we operate now that AI has changed the work, whatever is most broken and least claimed. You'll be handed problems, not projects.
• Partner with Finance and People on the R&D headcount plan, capacity model, budget governance, and senior onboarding.
• Improve escalation discipline — build the path by which a risk reaches the right leader fast, and make sure follow-through actually happens.
• Represent R&D leadership in rooms they can't be in.

Benefits

• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed