Chief of Staff, Office of the CEO

Zipline•South San Francisco, CA

1d•$125,000 - $300,000•Onsite

About The Position

Zipline is scaling quickly, and the highest-leverage company decisions need to become clear, well-owned, and executed at speed. We are hiring a Office of the CEO for someone who can operate at extremely high standards, absorb ambiguity fast, and turn leadership priorities into crisp decisions, operating rhythm, and follow-through. We care less about whether you have held one specific title before and more about whether you have been trained in environments with extreme standards: high-stakes decisions, demanding leaders, compressed timelines, sensitive information, and no room for sloppy follow-through. This is not a generic support function, a coordination layer, or a place to learn executive operating basics. The right people have exceptional judgment, extreme ownership, and the ability to move from board-level strategy to execution detail without losing speed or quality. You will work closely with Keller and the executive team on the company’s most important operating, communication, and leverage problems, especially when ownership is unclear, cross-functional, sensitive, or high-stakes.

Requirements

A background that trained you to operate close to high-stakes decisions, demanding principals, and unforgiving execution environments (e.g., mission operations, military leadership, investment banking, restructuring, elite legal practice, political campaigns, founder or CEO offices, private equity operations, luxury or fashion operations, live production, high-performance sports).
Exceptional performance in one of the following areas: executive support at the highest level, executive operations / Chief of Staff work, communications / narrative leadership, business operations, strategy and operations, program leadership, consulting, investing, founder's office, or another high-context operating role.
A track record of being trusted with ambiguous, sensitive, high-leverage work where the answer was not obvious, the context changed quickly, and weak execution had real consequences.
Outstanding written and verbal communication skills; ability to turn messy context into a sharp decision memo, recommendation, agenda, narrative, or follow-up plan with very little hand-holding.
Elite discipline in work that creates CEO leverage: calendar and time architecture, executive materials, leadership cadences, ownership tracking, communications, hiring loops, planning processes, and cross-functional project management.
Very high judgment, discretion, and maturity with sensitive leadership, talent, compensation, and organizational topics.
High agency, low ego, and unusually strong follow-through; ability to not wait for perfect direction, hide behind process, or confuse activity with impact.
Comfort switching altitude quickly: from board-level narratives to executive-team follow-up, from calendar detail to company operating rhythm, from sensitive communications to urgent cross-functional execution.
A serious appetite for intensity; desire to be close to hard, important company problems and energized by being held to a very high bar.

Responsibilities

Force clarity around critical CEO and executive-team decisions by separating signal from noise, framing tradeoffs, pressure-testing options, and driving follow-through until decisions become outcomes.
Run executive operating cadences with a very high bar for usefulness, ensuring meetings, offsites, materials, moderation, follow-up, and information flow make the company faster and sharper.
Take on high-priority projects that sit between functions, require executive alignment, or do not naturally fit within an existing team’s scope, moving these efforts from ambiguity to concrete plans, owners, deadlines, decisions, and measurable progress.
Extend the CEO's operating capacity across one of three lanes: executive leverage and time architecture, cross-functional operating execution, or communications and narrative, knowing when the CEO needs to be directly involved, when to protect their time, and when to create leverage by pushing others to own the work.