Head of Strategy & Operations, Office of the COO

Headway•New York, NY

3d•$251,200 - $314,000

About The Position

Headway is seeking a Head of Strategy & Operations, Office of the COO, to partner closely with COO Rob Sadow. This high-trust, high-impact individual contributor role reports directly to the COO and serves as a point of leverage for the executive team. The role runs core company operating processes, turns important priorities into action, strengthens executive-team operations, and helps ensure critical decisions and initiatives proceed with clarity and accountability. The position also works closely with the COO’s Executive Assistant to focus the COO’s time and attention on key decisions and priorities. The role owns company operating processes such as planning, OKRs, and other operating cadences, keeping them lightweight and automating work that does not require human judgment. It owns the weekly company OKR review and its follow-through, investigates problems using data and stakeholder input, and brings diagnoses, recommendations, and accountable owners. It serves as the first stop for decisions that would otherwise go to the COO, resolving matters within agreed decision rights and escalating others with options, recommendations, deadlines, owners, and resolution dates. It also takes on critical cross-functional initiatives without clear owners, defining problems, aligning stakeholders, and driving resolution or transitioning work to a permanent owner. In partnership with HRBP and Finance teams, the role supports organizational health and productivity, including aligning organizational structure with business needs, scoping and hiring key roles, and ensuring staffing ratios are aligned with talent competitors. The successful candidate has operated at an executive level, owned consequential outcomes, run company-wide processes, worked directly with senior executives during significant growth, and demonstrated strong strategic problem-solving, writing, hiring, board/investor materials, and use of AI and automation.

Requirements

Executive-level operating experience with accountability for 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.
Experience running an end-to-end company-wide process such as annual or quarterly planning, goal-setting, or business reviews, and ability to distinguish useful process from overhead.
Experience working directly with a CEO, COO, or executive team at a company that at least doubled in revenue during the candidate’s tenure.
Experience being trusted to attend meetings in an executive’s place 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 down complex problems and helping a team develop a vision and execution plan.
Exceptional writing ability, including communicating a complex, high-stakes issue and a clear recommendation in one page.
Ability to identify what matters in a messy situation, go to the 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 the narrative and supporting analysis.
Ability to use AI and automation to remove manual work from processes rather than adding people.

Nice To Haves

Prior Chief of Staff experience.
Consulting experience.
An MBA.

Responsibilities

Run 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 follow-through; investigate issues using data and stakeholder input, then provide a diagnosis, recommendation, and named owner.
Serve as the first stop for decisions that would otherwise go to the COO, making decisions within agreed decision rights and routing others to functional owners.
Bring decisions requiring the COO’s involvement with options, a recommendation, and a deadline, and ensure each decision has an owner and resolution date.
Resolve high-stakes, cross-functional initiatives that lack a clear owner by defining the problem, aligning stakeholders, and driving resolution or transitioning the work to a permanent owner.
Partner with HRBP and Finance teams to support organizational health and productivity, align organizational structure with business needs, scope and hire key roles, and assess staffing ratios.
Work closely with the COO’s Executive Assistant to focus the COO’s time and attention on important decisions and priorities.