Remote Chief Executive Assistant

DescriptionAbout Squared AwaySquared 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 Q3 2026 (July - September)What We're Looking ForThis 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 RoleOur work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically:Have established experience supporting senior executivesEnjoy variety and problem-solving over repetitive task workAre available and responsive during weekday business hoursTake a proactive approach and anticipate needs rather than waiting for directionStay effective when priorities change or when not everything is fully definedTreat confidentiality and discretion as non-negotiableStructure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executivesIf you see yourself in this list, you're likely a great match for how we work at Squared Away.What You'll Be Responsible ForExecutive Operations & Time ManagementManage and optimize complex executive calendars across time zonesAnticipate conflicts and proactively resolve scheduling issuesProtect executive focus by enforcing priorities and boundariesExecutive CommunicationManage executive inboxes with discretion and sound judgmentDraft, respond to, and triage correspondence on behalf of executivesEnsure urgent matters are surfaced promptly and appropriatelyTravel & LogisticsCoordinate domestic and international travel end-to-endPrepare detailed itineraries and anticipate changes or disruptionsPreparation & ExecutionPrepare meeting materials, agendas, presentations, and reportsTrack action items, deadlines, and follow-through across initiativesSystems & Process ImprovementCreate, document, and refine workflows to improve efficiencyIdentify tools and processes that reduce friction and increase clarityResearch & Strategic SupportConduct research on competitors, tools, vendors, and market trendsProvide concise summaries to support executive decision-makingDiscretion & TrustHandle sensitive and confidential information with absolute integrityWhat Success Looks Like in the First 90 DaysIn the first 90 days, successful Chief Executive Assistants at Squared Away typically:Actively take on client work and build momentum by supporting assigned clients successfullyBuild trust and rapport with their executive(s) through consistent communication and follow-throughDevelop a strong understanding of executive priorities, preferences, and working styleTake ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalationEstablish reliable systems for tracking tasks, deadlines, and follow-upsCommunicate clearly and confidently, even when priorities shift or information is incompleteMaintain discretion and professionalism while handling sensitive informationStructure their workday to balance availability, focused work time, and responsivenessThis is not about perfection. It's about progress, ownership, and building momentum.RequirementsMinimum Qualifications (Required)Applicants must maintain a permanent U.S. address in one of the following states:Alabama, Alaska, Arizona, California, Colorado, Florida, Georgia, Hawaii, Illinois, Indiana, Iowa, Kentucky, Louisiana, Maryland, Michigan, Missouri, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, WashingtonMilitary spouses living overseas on active orders are welcome to apply, provided they maintain a permanent address in one of the states listed above and can reliably support clients during U.S. business hours.Must be available during normal business hours Monday–Friday, 9 AM–5 PM (in your time zone) for regular client communicationThis role cannot be combined with another job that limits availability during these hoursAbility to commit a minimum of 20 hours per week, with flexibility to take on additional hoursAdministrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.Experience working remotely is strongly preferredReliable home office setup, including:Mac or PC computer with webcamHigh-speed internetSmartphone with email capabilitiesA designated, quiet workspace suitable for professional workSkills & Attributes We Look ForStrong written and verbal communication skills, able to clearly and concisely communicate in a variety of contextsProficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity using project management toolsExperience managing schedules, communication, and priorities across time zonesUnderstanding of cross-cultural communication in a global working environmentExceptional organization and attention to detailHigh emotional intelligence and situational awarenessComfortable working independently without constant directionTech-savvy and quick to learn new systems and toolsProactive mindset that anticipates needs rather than reactsBenefitsCompensation & Contractor DetailsThis is a fully remote 1099 independent contractor position.Contractors are paid for billable hours worked, with hourly rates determined by experience and tier level:Tier 1: $24/hourTier 2: $30/hourTier 3: $36/hourContractors submit time through Harvest Time Tracking for billable work completed during each client plan period, and payments are issued twice monthly.Most contractors support 2–4 clients at a time. Client opportunities are offered based on business needs, and contractors decide which opportunities to accept, allowing them to build a workload that aligns with their availability and business goals.Squared Away handles client acquisition, client contracts, billing, and invoicing so you can focus on providing exceptional executive support. You'll work with a vetted client base across a wide range of industries, including venture capital, consulting, finance, marketing, nonprofit, real estate, technology, and more.This is a fully remote role with the flexibility to build a client portfolio that fits your schedule.Authentic, not ArtificialWe value clear thinking, sound judgment, and authentic communication.We recognize that AI tools are increasingly part of how people work, and we support thoughtful, responsible use of them.During the application process, we're looking to understand how you think and communicate. Responses should reflect your own voice, experience, and decision-making. Submitting answers that are fully generated by AI, without your input or perspective, may impact your candidacy.If you move forward, it's because we see how you approach problems, communicate under pressure, and make decisions. We're not looking for perfection; we're looking for clarity, ownership, and professionalism.Reapplying?If you've applied previously and were not selected, we encourage you to reapply. We release updated versions of this application each quarter to reflect evolving needs and give returning candidates another opportunity to be considered.Privacy NoticeBy applying, you acknowledge and agree to our Candidate Privacy Notice.