Chief Executive Assistant (Generalist)

About Squared Away Squared Away supports founders, executives, and leadership teams operating at a high level of complexity and pace. Our assistants are not task-takers. They are trusted, strategic partners who bring structure, clarity, and follow-through to demanding environments. We exist to give people their most valuable resource back: time. That work requires judgment, discretion, and consistency, every single day. Squared Away maintains a rolling application for our Executive Assistant position. This posting is for Q2 2026 (April - June) What We're Looking For This is not an entry-level role, and it is not a side role. As a Chief Executive Assistant at Squared Away, you will support senior executives who expect proactive thinking, excellent communication, and dependable execution. You will manage competing priorities, anticipate needs before they are voiced, and operate with a level of ownership that mirrors in-house executive support. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards . What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically: Have established experience supporting senior executives Enjoy variety and problem-solving over repetitive task work Are available and responsive during weekday business hours Take a proactive approach and anticipate needs rather than waiting for direction Stay effective when priorities change or when not everything is fully defined Treat confidentiality and discretion as non-negotiable Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives If you see yourself in this list, you’re likely a great match for how we work at Squared Away. What You’ll Be Responsible For Executive Operations & Time Management Manage and optimize complex executive calendars across time zones Anticipate conflicts and proactively resolve scheduling issues Protect executive focus by enforcing priorities and boundaries Executive Communication Manage executive inboxes with discretion and sound judgment Draft, respond to, and triage correspondence on behalf of executives Ensure urgent matters are surfaced promptly and appropriately Travel & Logistics Coordinate domestic and international travel end-to-end Prepare detailed itineraries and anticipate changes or disruptions Preparation & Execution Prepare meeting materials, agendas, presentations, and reports Track action items, deadlines, and follow-through across initiatives Systems & Process Improvement Create, document, and refine workflows to improve efficiency Identify tools and processes that reduce friction and increase clarity Research & Strategic Support Conduct research on competitors, tools, vendors, and market trends Provide concise summaries to support executive decision-making Discretion & Trust Handle sensitive and confidential information with absolute integrity What Success Looks Like in the First 90 Days In the first 90 days, successful Chief Executive Assistants at Squared Away typically: Actively take on client work and build momentum by supporting assigned clients successfully Build trust and rapport with their executive(s) through consistent communication and follow-through Develop a strong understanding of executive priorities, preferences, and working style Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation Establish reliable systems for tracking tasks, deadlines, and follow-ups Communicate clearly and confidently, even when priorities shift or information is incomplete Maintain discretion and professionalism while handling sensitive information Structure their workday to balance availability, focused work time, and responsiveness This is not about perfection. It’s about progress, ownership, and building momentum.