Chief of Staff, R&D

Headway is building a new mental healthcare system everyone can access. R&D — Engineering, Product, Design and Data — is Headway's largest investment and the engine of our growth. 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.

Responsibilities

Own the R&D rhythm of business: leadership staff meetings, product & tech reviews, quarterly planning, R&D all-hands, board meeting prep etc; 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.

Requirements

You must have supported a product or engineering executive (or both) as their chief of staff; You have 10+ years across strategy, business operations, management consulting, product management, engineering leadership, or prior Chief of Staff roles; You have 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; You're a genuinely excellent writer. You can take a complex, contested topic and produce the brief, memo, or deck that moves a decision — and you can write in someone else's voice when the moment calls for it; You're technical enough to be credible. You don't need to write code, but you need to hold your own in a conversation about architecture, technical risk, and engineering trade-offs, and earn the trust of senior engineers; You operate through influence rather than authority, and you've built the standing to do it before — with peers who didn't report to you and executives who didn't have to listen; You bring structure to ambiguity without smothering speed, and you have the judgment to know which of those two matters more in a given week; You're AI-native in how you work — you've 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 have

healthcare, marketplace, or other multi-stakeholder business experience; time inside a company scaling through 1,000 people

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