Department: Office of the CEO Reports to: CEO Location: Remote (US, CT or ET preferred) Employment type: Full-time About Dapple Dapple is the Enterprise OS Cloud, a new category of AI infrastructure between the public cloud and the private data center. We give regulated enterprises and high-growth digital natives dedicated, in-country, single-tenant capacity to run production AI, extending the cloud ecosystems they already use rather than asking them to leave. We are an early-stage, venture-backed company moving quickly. About the role The Executive Assistant keeps the CEO's world running. Reporting to the CEO, this role owns her calendar, inbox, travel and day-to-day, freeing her to focus on the highest-leverage work at a company moving very fast. This is a senior, experienced EA role. The right person is an exceptional gatekeeper who knows which meetings matter and which do not, manages a complex calendar with judgment, and protects the CEO's time without being asked. They are organized, discreet and proactive, and the people around them are more effective because of them. Beyond supporting the CEO directly, this role helps keep the company's rhythm and culture intact, owning the things that matter but have no natural home, such as the offsite, team events and swag. Key responsibilities Executive support to the CEO: Own the CEO's calendar, inbox and travel, with the judgment to prioritize, decline and reschedule on her behalf. Be an exceptional gatekeeper: protect her time, surface what needs attention and keep her a step ahead of what is coming. Prepare her for meetings with agendas, materials, briefing notes and follow-ups. Handle scheduling, expenses, documents and the day-to-day so nothing slips. Plan and coordinate company programs and team moments, including the annual offsite, team events and swag. Keep the small but important things that hold the company together from falling through the cracks. Support broader executive and team coordination as needed Qualifications 5 or more years as an executive assistant to a CEO, founder or senior executive, ideally at a startup or in a fast-moving environment. An exceptional gatekeeper with mastery of complex calendars and the judgment to manage an executive's time independently. Exceptional organization, discretion and reliability, trusted with confidential and high-stakes information. Proactive and low ego: anticipates needs and owns the details, with no task too big or too small. Calm and steady under pressure in a high-change environment. Clear, concise written communication, comfortable acting in the CEO's voice. Preferred experience Long-tenured support of one or two executives, the kind of EA who becomes indispensable, is strongly preferred. Additional nice-to-haves: familiarity with the Microsoft 365 stack, DocuSign and common travel tools; experience supporting a distributed, remote-first team across time zones; experience coordinating events, offsites or team culture programs. Compensation and benefits Competitive base salary plus bonus and equity, calibrated to experience. Medical, dental, vision and disability insurance 401(k) Maternity and parental leave 6 weeks of PTO per year Flexible work schedules Three rounds: an initial screen; a take-home exercise on a real scheduling or prioritization scenario; and a final round with the CEO. We move quickly, with a typical end-to-end timeline under two weeks. Equal opportunity Dapple is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic. Experience: 5 years required