Executive Personal Assistant

Simplified Management, LLC; Auburn (ME); On-site; USD 60,000 - 90,000; Full time

Job summary

Simplified Real Estate is seeking an Executive & Personal Assistant to support the Founder across professional and personal priorities. You will protect time, organize commitments, manage logistics, and ensure follow-ups stay on track, without waiting for instructions.

You will learn the Founder's working style, preferences, relationships, and priorities well enough to anticipate needs and act proactively. You will coordinate meetings, travel, reservations, events, and professional touchpoints,

Qualifications

• Previous EA/PA experience required.
• Experience supporting a founder or senior leader.
• Ability to work proactively without daily direction.
• Excellent organization and follow-through.

Responsibilities

• Coordinate meetings, travel, reservations, and events.
• Manage logistics and protect the Founder’s time.
• Handle follow-ups and routine issues independently.
• Improve research, scheduling, and workflows with AI tools.

Skills

EA experience

Proactive mindset

Discretion

Organization

Communication

Independent worker

Travel logistics

AI tools

Tools

AI tools

Scheduling software

Job description

Create structure around the Founder's professional and personal priorities, anticipate what comes next, and keep important details moving without constant direction.

This is not a traditional reactive assistant role. We are looking for someone who does not wait for the Founder to provide a daily task list or point out every next step. You naturally look ahead, identify what needs attention, and create structure before small details become problems. You are comfortable making appropriate decisions independently, organizing competing priorities, and closing loops without constant supervision. You learn how people work, remember preferences and context, and use sound judgment to anticipate what will be needed next. If you take pride in being proactive, dependable, discreet, and consistently two steps ahead, this role is built for you.

THE ROLE

As our Executive & Personal Assistant, you will support the Founder across professional and personal priorities by protecting time, organizing commitments, managing logistics, and making sure important follow-ups stay on track. The expectation is not to wait for instructions, but to gradually learn the Founder's working style, preferences, relationships, and priorities well enough to anticipate needs and act proactively. You will coordinate meetings, travel, reservations, events, and professional touchpoints, resolve routine issues independently, and ensure details are accurate and ready in advance. You will also use AI and modern productivity tools to improve research, scheduling, communication, and recurring workflows.

ROLE HIGHLIGHTS

• 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

ABOUT US

Simplified Real Estate brings together our real estate businesses, including Candor and Simplified Management, with teams working across investments, brokerage, property management, operations, construction, and related functions. We are building an organization where strong execution, ownership, and sound judgment matter. This role works directly with the Founder and creates leverage across both professional and personal priorities by keeping commitments organized, relationships active, logistics accurate, and important details moving forward. You will have the opportunity to learn the businesses, understand the people and priorities behind them, and become increasingly trusted to manage more independently as familiarity and confidence grow.