Executive Personal Assistant

Simplified Management • Auburn, ME

1d • $55,000 - $70,000

About The Position

This role is for an Executive & Personal Assistant who will support the Founder across professional and personal priorities. The ideal candidate will proactively create structure, anticipate needs, and manage competing priorities with minimal supervision. This is not a reactive role; the candidate is expected to look ahead, identify what needs attention, and take initiative. Responsibilities include coordinating meetings, travel, reservations, events, and professional touchpoints, resolving routine issues independently, and ensuring details are accurate and ready in advance. The role also involves using AI and modern productivity tools to improve efficiency in research, scheduling, communication, and recurring workflows. The company, Simplified Real Estate, is building an organization where strong execution, ownership, and sound judgment matter. This position offers the opportunity to learn the businesses, understand the people and priorities, and grow into a trusted, independent manager of responsibilities.

Requirements

• Previous Executive Assistant or Personal Assistant experience required
• Experience supporting a founder, executive, or senior leader across professional and personal priorities
• Demonstrated ability to identify needs, take initiative, and work proactively without waiting for daily direction
• Exceptional organization, prioritization, and follow-through
• Strong judgment, discretion, and confidentiality
• Ability to make appropriate day-to-day decisions independently and operate with limited supervision
• Ability to manage multiple commitments, deadlines, logistics, and changing priorities with a high level of accuracy
• Strong written and verbal communication skills
• Ability to quickly learn preferences, routines, relationships, and priorities and retain important context
• Familiarity with personal logistics preferred, including travel, reservations, vendors, local geography, and related coordination.
• Comfortable using AI, productivity tools, and technology to improve efficiency
• Genuine interest in building a long-term working relationship with a Founder and learning the businesses surrounding the role

Responsibilities

• Support the Founder across professional and personal priorities by protecting time, organizing commitments, managing logistics, and making sure important follow-ups stay on track.
• Learn the Founder's working style, preferences, relationships, and priorities to anticipate needs and act proactively.
• Coordinate meetings, travel, reservations, events, and professional touchpoints.
• Resolve routine issues independently.
• Ensure details are accurate and ready in advance.
• Use AI and modern productivity tools to improve research, scheduling, communication, and recurring workflows.
• Create structure, protect someone's time, manage important details, and use good judgment to keep things moving independently.
• Anticipate needs, solve problems, and become a trusted partner behind the scenes.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed