Real Estate Executive Assistant
HeyDay Homes
Chicago, IL US
Posted ago
HeyDay Homes

The Executive Assistant is the Integrator who will work side-by-side with the Owner as the project manager, the doer, and the steady force that keeps the business focused. As outlined in the book Rocket Fuel, the role of the Executive Assistant/Integrator is to harness the ideas of the Owner/Visionary into an executable plan to keep the business moving forward.

Specifically, as the second-in-command to the Owner of Heyday Homes, the Executive Assistant will work alongside the Owner to execute her vision for growing the real estate team. The Executive Assistant will be responsible for managing all areas of the business, including sales, marketing, operations, and administration.

This position requires creativity and precision while managing a high level of communication. The ideal candidate will work well with minimal supervision, gradually taking on more responsibility and leadership, including assisting in hiring, training, and leading/overseeing additional team members.

As the right-hand person to the Owner, the Executive Assistant/Integrator is expected to protect the interests of the company as a partner.

Bottom line: if you are known for getting stuff done and want the challenge of working side-by-side with the Owner to grow something bigger, let’s talk!

Base salary range: Salary will be based on knowledge/skill set and experience.

Additional benefits include: 

  • Health insurance or subsidy
  • Referral fee (whether licensed or not) for any clients contributed to the team, paid post-close. 
  • Opportunity for additional bonuses
  • Paid vacation


  • Design and implement a client care system 
  • Develop and manage a referral or VIP process for vendors and past clients
  • Manage database cleanup and migration into one central CRM
  • Planning and coordinating events 
  • Create and manage a dynamic marketing plan that includes social media, website, email, print, and video content
  • Manage and prioritize multiple priorities 
  • Stick with projects through the completion 
  • Organize and manage CEO's schedule, emails, and client care concerns


  • Bachelor's degree or equivalent experience 
  • Experience in event planning or management is preferred 
  • Strong management experience in real estate 
  • High level of emotional intelligence and assertiveness with the ability to read and handle situations appropriately.
  • Great grammar and attention to detail 
  • Open to taking initiative when they see opportunities to improve an experience
  • High-level time-blocker 
  • Ability to work a room and make people feel good 
  • High level of responsiveness with a proven track record of accomplishing goals 
  • Ability to self-manage and create structure 
  • Critical thinking mindset 
  • Ability to provide 3-5 references upon request

$50,000 - $60,000 yearly
About HeyDay Homes

We are a small (but mighty) woman-owned real estate business serving downtown Chicago and the surrounding suburbs. We focus on helping women and growing families make intentional decisions about their homes. We aim to curate every detail of the buying and selling process to make it as stress-free and streamlined as possible and strive to be the friend that has our clients’ back every step of the way. 

We value intentional decision-making, continuously growing and learning, putting relationships first and celebrating everyday victories.

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