Executive Compressed Jobs (NOW HIRING)

Zipline is scaling quickly, and the highest-leverage company decisions need to become clear, well-owned, and executed at speed. We are hiring a Chief of Staff into the Office of the CEO, looking 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.

• You will force clarity around critical CEO and executive-team decisions. You will separate signal from noise, frame the real tradeoffs, pressure-test the options, and drive follow-through until decisions become outcomes.
• You will run executive operating cadences with a very high bar for usefulness. Meetings, offsites, materials, moderation, follow-up, and information flow should make the company faster and sharper, not create process theater.
• You will take on high-priority projects that sit between functions, require executive alignment, or do not naturally fit within an existing team's scope. You will move these efforts from ambiguity to concrete plans, owners, deadlines, decisions, and measurable progress.
• You will extend Keller's operating capacity across one of three lanes: executive leverage and time architecture, cross-functional operating execution, or communications and narrative. In every lane, you will know when Keller needs to be directly involved, when to protect his time, and when to create leverage by pushing others to own the work.

• A background that trained you to operate close to high-stakes decisions, demanding principals, and unforgiving execution environments. We are open to non-traditional paths: 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, or other environments where judgment, pace, discretion, and follow-through are non-negotiable.
• Exceptional performance in one of the lanes we are hiring for: 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; you can turn messy context into a sharp decision memo, recommendation, agenda, narrative, or follow-up plan with very little hand-holding.
• Elite discipline in the 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; you do 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. These roles are for people who want to be close to hard, important company problems and are energized by being held to a very high bar.

This will be an in-office role based out of our South San Francisco HQ. Must be able to travel up to 30% of the time both nationally and internationally.

The starting cash range for this role is $125,000 - $330,000; please note that this is a target, starting cash range for a candidate who meets the minimum qualifications for this role. We are always open to negotiation. The final cash pay for this role will depend on a variety of factors, including a specific candidate's experience, qualifications, skills, working location, and projected impact. The total compensation package for this role may also include: equity compensation; overtime pay; discretionary annual or performance bonuses; sales incentives; benefits such as medical, dental and vision insurance; paid time off; and more.

Zipline is an equal opportunity employer and prohibits discrimination and harassment of any type without regard to protected characteristics.

We value diversity at Zipline and welcome applications from those who are traditionally underrepresented in tech. If you like the sound of this position but are not sure if you are the perfect fit, please apply!