Executive Assistant – Business & Personal
We are looking for a high-level Executive Assistant who is organized, proactive, resourceful, and capable of keeping a fast-moving executive one step ahead.
This role supports both the business and personal side of the executive’s life.
You will work directly with the owner of a high-volume real estate team and growing brokerage, helping manage communication, scheduling, follow-up, projects, personal logistics, and the many moving pieces that come with running multiple businesses.
This is not a traditional administrative assistant role.
The right person will take ownership, close loops, anticipate what is needed, and make sure important things do not fall through the cracks.
What You’ll Own
Business Support
- Manage calendar, meetings, appointments, and changing priorities
- Organize email, calls, messages, and incoming requests
- Determine what needs the executive’s attention and what can be handled independently
- Follow up with employees, vendors, clients, attorneys, and outside partners
- Track projects, commitments, and outstanding items through completion
- Prepare information, notes, documents, and follow-up items
- Conduct research and help gather information for decisions
- Coordinate meetings, events, and travel
- Help protect the executive’s time and keep priorities moving
Personal Support
- Schedule personal appointments and commitments
- Coordinate household vendors, repairs, deliveries, and services
- Make reservations and coordinate personal travel
- Handle purchases, returns, gifting, and online orders
- Assist with family scheduling and logistics when needed
- Research and arrange services, appointments, or purchases
- Handle errands and occasional local pickups or drop-offs
- Help coordinate personal events, holidays, gifts, and projects
- Track personal follow-ups and deadlines
No two days will look exactly the same.
One hour you may be following up on an important business project, and the next you may be coordinating a contractor, making a reservation, returning an item, or solving a scheduling issue.
You need to be comfortable moving between both worlds.
What We’re Looking For
- Previous Executive Assistant experience supporting an owner, founder, CEO, or high-level executive
- Experience handling both business and personal responsibilities strongly preferred
- Exceptional organization and follow-through
- Strong written and verbal communication
- Excellent judgment and discretion
- Ability to prioritize quickly
- Highly resourceful and comfortable figuring things out independently
- Strong attention to detail
- Comfortable with technology and learning new systems
- Confident communicating with employees, clients, vendors, and professionals
- Comfortable handling confidential information
- Reliable transportation and ability to travel locally when needed
You’ll Be a Strong Fit If
You hear, “Can you handle this?” and take ownership until it is completely finished.
You naturally follow up without being reminded.
You anticipate what will be needed next.
You are comfortable handling important business matters and personal tasks with the same level of professionalism.
You understand that the purpose of this role is to remove things from the executive’s plate and brain, not simply wait for assignments.
You Are Probably NOT a Fit If
- You need detailed instructions for every task
- You require a highly predictable day
- You struggle when priorities change
- You wait for someone else to follow up
- You view personal tasks or errands as outside the scope of the role
- You struggle with urgency
- You complete your part of a task but do not make sure the overall issue gets resolved
About Us
The Sarah Leonard Team is a high-volume Chicagoland real estate team completing hundreds of transactions annually. Legacy Properties is our growing brokerage.
Our environment is fast-paced, entrepreneurial, and results-driven.
This position works directly with the owner and will become a highly trusted part of both her professional and personal day-to-day life.
We are looking for someone who wants to become a true right hand, not simply an administrative assistant.
To Apply
Please submit your resume along with brief answers to the following:
- Tell us about the highest-level executive or family you have supported and what you were responsible for.
- Have you handled both business and personal responsibilities? Please give examples.
- Give an example of something you were asked to handle with very little direction.
- How do you keep track of follow-ups and make sure nothing falls through the cracks?
- Are you comfortable handling errands, household coordination, appointments, travel, purchases, and other personal responsibilities in addition to business support?
- Do you have reliable transportation and the ability to travel locally as needed?
Pay: $48,000.00 - $63,201.39 per year
Benefits:
- 401(k)
- Health insurance
- Referral program
Work Location: In person
