Executive Assistant

Senior Executive Assistant for UHNW Founder/Investor Woodside, CA (office-based with flexibility)Compensation: $185,000–$205,000 base DOE + full benefitsGeneral business hours with flexibility; responsiveness outside standard hours requiredSupervising a team of 4- 5 virtual assistants, in office -- WoodsideSeeking a low-ego, highly intuitive, tech-savvy Senior Executive Assistant to support a dynamic CEO/Founder. This is a business-focused role requiring strong judgment, anticipation, and the ability to pivot quickly while keeping systems, people, and priorities aligned.The ideal candidate is warm and personable, able to read a room instinctively, and comfortable supporting an independent, fast-moving leader.The role works closely with a Chief of Staff, Estate Manager, Personal Assistants, and a 24/7 virtual assistant team. What Success Looks LikeThe principal stays focused and in flowShifting priorities are managed seamlesslySystems run smoothly and improve over timeThe broader assistant team stays informed and alignedKey ResponsibilitiesExecutive SupportServe as the primary, Woodside-based Executive AssistantAnticipate needs; engage proactively with prepared questionsRespond to requests with sound judgment, discretion, and efficiencyTrack evolving priorities and adjust plans in real timeCalendar & TravelManage complex, ever-changing executive calendarsOversee domestic and international travel, primarily private aviationHandle logistics, briefing materials, and contingencies at a high levelTeam & Systems LeadershipLead and coordinate a rotating team of virtual and on-site assistantsAct as escalation point when issues ariseEnsure smooth handoffs, coverage, and continuityBuild, refine, and maintain effective systems and workflowsCollaborationPartner closely with the Chief of Staff and Estate ManagerCoordinate with drivers, household staff, and Personal AssistantsSupport social calendars, event oversight, and gifting as neededExperience & ProfileSenior EA experience supporting C-level CEOs/Founders or UHNW principals onlyHighly tech-savvy with strong systems fluencyProven success in fast-paced, high-change environmentsAdvanced calendar and travel management expertiseWarm, polished, and emotionally intelligent; reads a room wellCalm, positive, and action-orientedFlexible and responsive to after-hours changesWorking StyleLow ego, high accountabilityProactive, intuitive, and efficientComfortable with independent, dynamic leadership stylesAnticipates needs rather than reacting