Head of Strategy & Operations, Office of the COO

Headway•New York, NY

About The Position

Headway is building a new mental healthcare system to make care more accessible. Its platform helps providers manage practice administration and supports patients, providers, and payers. The company reports serving more than 90,000 providers across all 50 states and more than 2.6 million patients, and is a Series D company. Headway is seeking a Head of Strategy & Operations for the Office of the COO to partner closely with COO Rob Sadow as a senior individual contributor and trusted point of leverage. Reporting directly to the COO, this role runs core company operating processes, translates key priorities into action, strengthens executive-team operations, and helps ensure that important decisions and initiatives progress with clarity and accountability. The role has significant exposure to the executive team and broader business, and works closely with the COO’s Executive Assistant to focus the COO’s time and attention on critical decisions and priorities. The role owns company planning, OKRs, and other operating cadences; drives execution through weekly company OKR reviews; manages the decision queue; and resolves high-stakes cross-functional initiatives that lack a clear owner. In partnership with HRBP and Finance teams, it also supports organizational health and productivity, including organization design, key-role scoping and hiring, and staffing alignment. The successful candidate has operated at executive level, led company-wide processes, worked directly with senior executives through significant company growth, and is skilled at writing, analysis, decision-making, hiring, and using AI and automation to reduce manual work.

Requirements

Experience operating at executive level and owning outcomes, such as as a COO or Head of Operations at an earlier-stage company, or a VP, Senior Director of Strategy & Operations, or GM at a larger company.
Ability to identify and describe results for which you were accountable.
Experience running a company-wide process end to end, such as annual or quarterly planning, goal-setting, or business reviews, and distinguishing useful process from overhead.
Experience working directly with a CEO, COO, or executive team at a company that at least doubled in revenue during your tenure.
Experience being trusted to attend meetings for an executive and make decisions on their behalf.
Experience hiring senior people through a rigorous process and building or rebuilding a team.
Strategic problem-solving ability, including breaking problems into parts and helping a team develop a vision and execution plan.
Exceptional writing skills, including the ability to explain a complex, high-stakes issue in one page with a clear trade-off and recommendation.
Ability to quickly identify what matters in a messy situation, gather information from people and data closest to the problem, form a point of view, and present options with a clear recommendation.
Experience owning board or investor materials, including narrative and analysis.
Ability to use AI and automation to reduce manual work rather than add staff.

Nice To Haves

Chief of Staff experience.
Consulting experience.
MBA.

Responsibilities

Run key company operating processes, including planning, OKRs, and other important operating cadences, keeping them lightweight and automating work that does not require human judgment.
Own the weekly company OKR review and its outputs; investigate issues using data and direct conversations, develop a diagnosis and recommendation, and identify an owner.
Serve as the first stop for decisions that would otherwise go to the COO; make decisions within agreed decision rights and route others to functional owners.
Bring decisions requiring the COO’s input with options, a recommendation, and a deadline, and ensure every decision has an owner and resolution date.
Resolve high-stakes cross-functional problems without a clear owner by defining the problem, aligning stakeholders, and driving it to resolution or transferring it to a permanent owner.
Partner with HRBP and Finance to support organizational health and productivity, including organization structure, scoping and hiring for key roles, and staffing-ratio alignment.
Work with the COO’s Executive Assistant to focus the COO’s time and attention on important decisions and priorities.
Use AI and automation to remove manual work from processes.
Own board or investor materials, including their narrative and supporting analysis.