About This Role

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.

You Will

• 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.

You'd Be a Great Fit If...

• 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.

Compensation and Benefits:

The expected base pay range for this position is $230,000-$300,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
  
  • 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