Senior Executive Assistant- Freelance, Remote

• Own complex calendar orchestration for 2–3 founders; anticipate needs, resolve conflicts, and build buffers
• Drive attendee coordination, agendas, materials, and pre-reads; ensure all meetings are “show-up ready”
• Proactively connect dots across leaders and teams; suggest when to consolidate or sequence related discussions

• Manage end-to-end travel (flights, hotels, ground) with complete itineraries and contingency planning
• Handle rapid changes and troubleshooting with minimal disruption to executive timelines
• Own expense reconciliation, receipt capture, coding, and timely submission; follow up proactively on gaps

• Triage executive inboxes; draft standard responses; flag true priorities and deadlines
• Track follow-ups and commitments to ensure nothing falls through the cracks
• Interface professionally with internal teams, vendors, investors, and external partners

• Independently plan and execute team offsites and corporate events from concept to debrief
• Lead venue sourcing, vendor negotiations, budget tracking, logistics, catering, A/V, and communications
• Deliver seamless experiences without hand-holding or basic how-to questions

• Draft and format slide decks and documents to professional standards
• Manage files and materials; assemble briefing packets and meeting books
• Coordinate board/investor scheduling, gift logistics, relationship tracking, and cross-functional follow-ups
• Track action items post-meeting and drive accountability across teams

• Senior-level EA experience supporting founders/C-level executives for 5+ years; not a first or second EA role
• Proven, end-to-end ownership of team offsites and corporate events (venue/vendor selection through on-site execution and debrief)
• Demonstrated excellence in complex calendar orchestration across multiple executives and stakeholders
• Advanced experience with full-cycle travel and expense management in fast-paced, high-change environments
• Strong written communication and executive presence; able to represent leaders with discretion and judgment

• Technical: Google Workspace or Microsoft 365 power user; expert Google/Outlook calendar management; expense tools (e.g., Expensify/Concur); travel platforms; Slack/Zoom; presentation building
• Operational: Vendor sourcing and negotiation; budget tracking; project plans, run-of-show, and debriefs; file and knowledge organization
• Communication: Crisp writing, precise meeting prep, confident stakeholder interfacing, proactive status updates
• Judgment: Independent decision-making, prioritization under pressure, ability to anticipate needs and manage trade-offs
• Traits: Type A organization, high ownership, resourceful problem-solver, calm under pressure, high discretion, low-ego team player

• Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up.
• Internet speed of at least 40MBPS
• Headset with an extended mic that has noise cancellation and a webcam
• Back-up computer and internet connection
• Quiet, dedicated workspace at home

• You are a proactive self-starter who anticipates needs and takes action without waiting for direction
• You’ve independently run team offsites and corporate events end-to-end and love making complex logistics look effortless
• You thrive in fast-moving tech/startup environments, handle last-minute changes with grace, and keep leaders focused on what matters
• You connect dots across people and projects, think two steps ahead, and uphold impeccable standards in service of the executive team
• You’re seeking a true senior EA seat—not a training ground—and you take pride in professional maturity and discretion

Benefits