Chief of Staff, Office of the CEO

About Zipline Zipline is the world’s largest and most experienced drone delivery service. We are on a mission to serve all humans equally by ensuring access to food, medicine and essential goods anytime, anywhere. We design, build, and operate the world’s largest autonomous logistics system, delivering critical supplies quickly and reliably. Today, Zipline operates on four continents, makes a delivery somewhere in the world every 30 seconds, and has completed millions of deliveries to date, including blood, vaccines, medical supplies, food, and retail products.  Our customers include the world’s largest and most prominent healthcare systems, governments, retailers, restaurants and global businesses who rely on us to save lives, reduce emissions, increase economic opportunity, and provide delivery from point A to point B as fast as possible. The drone is only 15% of what we’ve built to enable seamless, reliable, global operations. Our system strengthens supply chains, reduces congestion, and gives people time back. With more than 140 million commercial autonomous miles safely flown, Zipline is redefining access to healthcare, consumer products, and food across the globe. We operate at a global scale and are looking for practical problem solvers who thrive on real-world challenges and rapid growth. Our team is motivated by building systems that have a direct, meaningful impact on people’s lives and by scaling the future of logistics. We are seeking people who sculpt from first principles, enjoy facing adversity, and can do the impossible at record breaking speeds. About You & the Role 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. What You’ll Do 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. What You’ll Bring 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.