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)

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 suppo...