Chief of Staff, R&D

About

Headway is building a new mental healthcare system, rewired for access and affordability. The company is a Series D startup with $325M+ in funding, aiming to make therapy more accessible and affordable by solving the biggest barriers such as insurance and administrative challenges using software.

About This Role

As Chief of Staff, R&D, you will own the operating system that allows the organization to decide quickly and stay aligned. This Director-level individual contributor role involves running operations for the R&D org including quarterly and annual planning, headcount prioritization, escalation processes, organizational design, budget governance, and more. This role is critical to cross-functional alignment across Product, Engineering, Data, and Design teams and requires solving high-priority, ambiguous problems through influence rather than authority.

You Will

• Own the R&D rhythm of business including leadership staff meetings, product & tech reviews, quarterly planning, R&D all-hands, board meeting preparation.
• Manage the R&D planning cycle end to end coordinating across teams and setting commitments.
• Surface trade-offs to leadership with clear options and recommendations.
• Create board materials, strategy reviews, decision memos, and communications for the leadership team.
• Act as connective tissue across the org, spotting misalignment early and helping leaders converge on direction.
• Tackle highest-priority, least-owned problems such as org design and capacity alignment.
• Partner with Finance and People on headcount planning, capacity modeling, and budget governance.
• Improve escalation discipline to ensure risks are escalated and managed appropriately.
• Represent R&D leadership when they cannot be present.

You'd Be a Great Fit If...

• You have supported product or engineering executives as Chief of Staff.
• Have 10+ years of experience across strategy, business operations, management consulting, product management, engineering leadership, or Chief of Staff roles.
• Deep fluency in R&D organizations including product development lifecycle and capacity planning.
• Excellent writing skills to produce clear memos and communications for leadership.
• Technical credibility enough to engage with engineering discussions on architecture and trade-offs.
• Operate through influence rather than authority and have built strong peer and executive relationships.
• Ability to bring structure to ambiguity while maintaining speed and judgment.
• AI-native in work style with a strong point of view on its impact on R&D organizations.
• Bonus: healthcare, marketplace experience or experience at companies scaling through 1,000 people.

Compensation and Benefits

The expected base pay range for this position is $230,000-$300,000 annually, depending on qualifications, experience, and location. The role may be eligible for equity grants. Headway offers a comprehensive total rewards package including health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity.