Military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back.
Chief Executive Assistant
Location
Alabama + 21 moreAll locations: Alabama | Alaska | Arizona | California | Colorado | Florida | Hawaii | Illinois | Iowa | Kentucky | Louisiana | North Carolina | Ohio | Maryland | Michigan | Missouri | Pennsylvania | South Carolina | Tennessee | Texas | Virginia | Washington
Posted
5 days ago
Salary
$24 - $36 / hour
Seniority
Lead
Job Description
Chief Executive Assistant
Squared Away
• Manage and optimize complex executive calendars across time zones. • Anticipate conflicts and proactively resolve scheduling issues. • Protect executive focus by enforcing priorities and boundaries. • 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. • Coordinate domestic and international travel end-to-end. • Prepare detailed itineraries and anticipate changes or disruptions. • Prepare meeting materials, agendas, presentations, and reports. • Track action items, deadlines, and follow-through across initiatives. • Create, document, and refine workflows to improve efficiency. • Identify tools and processes that reduce friction and increase clarity. • Conduct research on competitors, tools, vendors, and market trends. • Provide concise summaries to support executive decision-making. • Handle sensitive and confidential information with absolute integrity.
Job Requirements
- 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, Washington
- Military 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 communication.
- Ability to commit a minimum of 20 hours per week, with flexibility to take on additional hours.
- Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
- Experience working remotely is strongly preferred.
- Reliable home office setup, including:
- Mac or PC computer with webcam
- High-speed internet
- Smartphone with email capabilities
- A designated, quiet workspace suitable for professional work.
- Strong written and verbal communication skills, able to clearly and concisely communicate in a variety of contexts.
- Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity using project management tools.
- Experience managing schedules, communication, and priorities across time zones.
- Understanding of cross-cultural communication in a global working environment.
- Exceptional organization and attention to detail.
- High emotional intelligence and situational awareness.
- Comfortable working independently without constant direction.
- Tech-savvy and quick to learn new systems and tools.
- Proactive mindset that anticipates needs rather than reacts.
Benefits
- This is a fully remote 1099 independent contractor position.
- Contractors are paid for billable hours worked.
- Hourly rates determined by experience and tier level.
- Tier 1: $24/hour
- Tier 2: $30/hour
- Tier 3: $36/hour
- Contractors submit time through Harvest Time Tracking for billable work.
- Payments are issued twice monthly.
- Most contractors support 2–4 clients at a time.
- Squared Away handles client acquisition, client contracts, billing, and invoicing.
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Kaseya CareersKaseya is the leading provider of complete IT infrastructure and security management solutions for Managed Service Providers (MSPs) and internal IT organizations worldwide powered by AI. Founded in 2000, Kaseya currently serves customers in over 20 countries across a wide variety of industries and manages over 15 million endpoints worldwide.
Role Description We are seeking a highly experienced Senior Executive Assistant to support a member of Kaseya’s executive leadership team. This role serves as a strategic partner, helping optimize executive effectiveness through exceptional organization, proactive planning, and seamless coordination across a fast-paced, high-growth environment. The ideal candidate is a trusted advisor who demonstrates sound judgment, anticipates needs, manages competing priorities, and operates with professionalism and discretion at the highest levels of the organization. Key Responsibilities - Manage a complex executive calendar, travel arrangements, and meeting logistics with exceptional attention to detail and foresight. - Partner closely with executive leadership to align priorities, maximize productivity, and ensure focus on high-impact business initiatives. - Serve as a trusted point of contact and liaison between the executive, senior leaders, employees, customers, and external stakeholders. - Prepare, coordinate, and manage executive communications, presentations, briefing materials, and meeting follow-ups. - Anticipate executive needs, identify potential challenges, and proactively develop solutions to support efficient decision-making and execution. - Coordinate cross-functional activities and special projects, ensuring deadlines and deliverables are met. - Handle highly confidential information with discretion and professionalism. Qualifications - 8–12+ years of experience supporting C-level executives in complex, fast-paced, and high-growth organizations. - Proven ability to manage competing priorities while maintaining exceptional attention to detail and accuracy. - Outstanding judgment, professionalism, and discretion when handling sensitive and confidential information. - Exceptional organizational, communication, and stakeholder management skills. - Highly proactive, resourceful, and capable of operating independently with minimal direction. - Strong business acumen and the ability to navigate organizational complexity effectively. - Advanced proficiency with Microsoft Office Suite, collaboration tools, and executive productivity platforms. Preferred Qualifications - Experience supporting executives within technology, SaaS, or high-growth private equity-backed organizations. - Experience coordinating cross-functional projects and executive-level initiatives. - Demonstrated ability to build strong relationships across all levels of an organization and influence outcomes through collaboration. Company Description Kaseya is the leading provider of AI-powered IT management and cybersecurity software, serving Managed Service Providers (MSPs) and internal IT organizations worldwide. Our comprehensive platform helps organizations efficiently manage, secure, and automate their IT environments, driving operational efficiency and long-term business success. Founded in 2000, Kaseya has built a culture centered around innovation, accountability, and results. We are a high-growth, high-performance organization that values individuals who are driven, adaptable, and committed to delivering exceptional outcomes for our customers and teammates alike.


