Executive/Personal Assistant

Executive/Personal Assistant

The Investment Real Estate Group of Companies is seeking a York based Executive/Personal Assistant to work directly with the CEO.

The Business:

The Investment Real Estate Group of Companies (IREGC) is composed of real estate centric entities focused on the self storage industry. The various companies provide brokerage services, property management, development and construction services and insurance products. In addition, we own a growing portfolio of 36 self storage properties. Our market area includes the 12 States in the Mid-Atlantic and Northeast. Learn more at www.irellc.com.

The Environment:

IREGC currently employs 50 people overall with 16 of those in the home office. We have converted an old stone grist mill built in 1831 and the adjoining miller’s house into our offices. The setting is pastorial and safe. We run the various businesses using the EOS (Entrepreneurial Operating System) methodology. At times the work can be hectic and other times very mellow; adaptability is key. IREGC employees are team oriented where all colleagues wear many hats and help each other succeed. While business is the priority, colleagues are encouraged to live healthy, balanced lives. Our company is guided by the core values of doing the right thing for our clients; being enthusiastic, energetic, tenacious and competitive; driving the miles, working hard and smart; having fun; and being caring, compassionate and authentic.  We are rapidly growing, and this is an excellent opportunity for the right candidate.

The Role:

The CEO of IREGC is a highly driven, fast paced, goal oriented, successful individual. He is intelligent, quick thinking and a risk taker. For those who know the DISC system, he is a very high D personality, yet has a friendly people-centric demeanor. We are seeking an Executive Assistant who will:

  • Be scrupulously organized and love taking care of people
  • Work thoroughly and independently, getting things done in a professional manner without burdening the CEO unless events demand it
  • Be the positive first impression for the firm’s customers, clients and friends
  • Be extremely pro-active in supporting administration and operations
  • Be open and embracing as new ideas and projects come up (at an amazing rate)
  • Be a lateral thinker and problem solver
  • Possess a positive “can do” attitude, knowing that any issue that arises can be overcome, solved, eradicated, left behind, gotten around, defeated and just plain taken care of!

There are two aspects to this role; the personal side and the business side.

On the personal side, we are looking to support the CEO with tasks like:

  • Travel and accommodation arrangements in the U.S. and around the world
  • Meeting and conference arrangement and confirmation
  • Organizing his office
  • Anticipating needs and wants in daily operations and preparing accordingly
  • Completing family projects such as publishing family member biographies, reunion organizing and
    photo/video production oversight
  • Personal effects – such as getting coffee and an occasional lunch, getting him to the airport or train, UPS/FedEx/USPS, cards and gifts for friends and family, family foundation projects, sporting event prep, assisting in supporting spouse’s charitable activities, supporting CEO’s charitable activities (Gilliland Family Foundation, Penn State, Church, Self Storage Association Foundation, various Board roles), etc.

On the business side, we’re looking for support in:

  • Email and calendar management. Making sure the CEO is where he needs to be on time and prepared
  • Travel arrangements for the CEO and his family
  • Handling general correspondence (email, phone calls, texts) independently as possible
  • Manage multi-state real estate licensing procedures for the CEO
  • Keeping the CEO up-to-date on all technology including iPhones, iPads, networks and computers
  • Handling general administration including financial and legal activities
  • Handling operational tasks including mail, office supplies, etc.
  • Overseeing all activities of the office, from the mundane to the extraordinary
  • Answering phones/receptionist activities
  • Free the CEO from the mundane and non-essential so that he can think and lead

We are looking for someone who thrives in an environment of growth, change and creativity with each day being a little different from the last. We’re also looking for someone who likes and is capable of working independently. We’re looking for someone grounded, operational and organized. One who is stable, unfazed and confident in their actions.  The job description of an Aide-de-Camp comes to mind.

Our ideal candidate will:

  • Add energy to every conversation.
  • Always be positive and have fun at work.
  • Highlight good work from your team members.
  • Leave things more organized than you found them.
  • Get smarter at your job through training, books, apps, etc.
  • Figure out what didn’t work and make sure it is right the next time.
  • Surface and highlight difficult decisions.
  • Encourage curiosity.
  • Ask why.


We’re looking for someone with existing high level experience in this kind of role with a suite of glowing personal references. You must have traveled so you understand the ins and outs of “planes, trains and automobiles”. It would be helpful if you have experience with prior executive assistant positions. You have a good understanding of online products, the process of production and the business of sales and marketing. Real estate experience is a plus but not required. And of course a pleasant and engaging personality is a must.

Application Process:

  1. Please fill out the following online questionnaire: https://docs.google.com/forms/d/e/1FAIpQLSfUQFroRDJpaoCksG4ncugc6JgiXb-KJlhA8A3z-BWdnVWcWQ/viewform?usp=sf_link
  2. Email your resume and cover letter to [email protected]
  3. We will meet with the final applicants in person.

We look forward to hearing from you,

The IREGC Team