Chief of Staff, R&D at Headway · LumiJobs

Responsibilities

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.
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.

Chief of Staff, R&D

Responsibilities

Qualification

Required

Benefits

Company

Headway

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