Chief Executive Assistant

About Mosaic Talent Consulting and Squared Away

Mosaic Talent Consulting aims to aid job seekers in assembling their optimal careers by presenting a variety of verified, high-quality opportunities. We do not function as a staffing agency or hire for these roles directly, instead aggregating and authenticating positions from genuine employers.

Squared Away supports high-level founders, executives, and leadership teams by offering strategic assistant partnerships. Our assistants function not just as task executors but as trusted partners who bring structure, clarity, and reliable follow-through in demanding, fast-paced contexts.

Our mission is to return the most valuable resource to people: their time. This necessitates sound judgment, discretion, and consistent performance every day.

Position Overview

Squared Away operates an ongoing application process for Chief Executive Assistant roles. This posting covers the third quarter of 2026 (July through September). This position is neither entry-level nor a part-time side role.

As a Chief Executive Assistant, you will provide support to senior executives who require proactive problem-solving, exceptional communication, and reliable task completion. You must handle multiple priorities, anticipate needs before they arise, and exhibit a level of ownership comparable to internal executive support roles.

Work Environment and Ideal Candidate Traits

• Proven background supporting senior executives effectively.
• Preference for dynamic challenges and problem resolution over repetitive duties.
• Availability and responsiveness during standard weekday business hours.
• Proactive mindset anticipating needs without waiting for guidance.
• Ability to maintain effectiveness amid shifting priorities or uncertainty.
• Commitment to confidentiality and discretion as fundamental principles.
• Organized work schedule featuring dedicated morning and afternoon blocks to ensure availability, focus, and timely communication.

Key Responsibilities

• Manage and optimize complex calendars for executives across multiple time zones, anticipating and resolving scheduling conflicts.
• Safeguard executive focus by enforcing priorities and boundaries effectively.
• Handle executive inboxes using discretion and sound judgment, including drafting, responding, and triaging communications.
• Promptly identify and escalate urgent matters as appropriate.
• Coordinate complete travel arrangements, both domestic and international, including detailed itineraries and contingency planning.
• Prepare meeting materials such as agendas, presentations, and reports, and track follow-up actions and deadlines.
• Develop, document, and refine workflows and systems to improve operational efficiency and reduce friction.
• Conduct research related to competitors, tools, vendors, and market trends, providing concise summaries to inform executive decisions.
• Handle all sensitive and confidential information with the utmost integrity and professionalism.

Expectations for the First 90 Days

• Begin actively supporting clients and gaining momentum in responsibilities.
• Establish trust and strong communication channels with executives.
• Understand executive priorities, preferences, and working styles thoroughly.
• Take ownership of calendar and inbox management, proactively resolving issues and anticipating needs.
• Implement reliable task and deadline tracking systems.
• Communicate clearly and adaptively amid changing priorities or incomplete information.
• Maintain strict discretion and professionalism with confidential matters.
• Effectively structure daily work to balance availability, focused work, and responsiveness.

Minimum Qualifications

Candidates must maintain a permanent U.S. residence during their tenure.

Additional Information

This role is an independent contractor position designed for experienced professionals who desire flexibility without compromising high standards. The role demands full-time commitment during weekday business hours in an onsite setting.