Tech-Savvy Ambitious Executive Administrative Assistant To CEO

Are you someone who likes to be involved? Someone who isn’t intimidated by multiple projects, a myriad of phone calls, answering ongoing questions from clients and colleagues, and onboarding an important new project… all before lunch.

Do you also envision being that go-to person for a dynamic company – a person who keeps everything going for the owner, and becomes a trusted confidant / chief of staff who shares in the company’s growth and success?

We are a multiple-entity Chicago-area speaking/consulting/legal firm that focuses on training, speaking, and corporate services. The entities are Speak Your Way To Cash® LLC and Mobile General Counsel® PLLC. The visionary behind both brands is Attorney Ashley N. Kirkwood. We are seeking a dynamic, motivated project assistant to help take this enterprise to the next level.

The ideal candidate should have an executive assistant background, be detail-oriented and organized, and be willing to take on multiple assignments. You must also be technologically proficient, and remain cool and professional when six people are looking for answers on four different projects. “Not my job” is not in your vocabulary. Instead, you say “I’ll handle it”, and then do. We’d also prefer someone who looks to improve processes, has their own ideas, and has the confidence to offer them.

This is a full-time, remote position. Post pandemic, occasional visits to the Chicago area. Occasional travel is a possibility. This is a position that could result in a long, satisfying career.

Competitive salary – $38K to $45k, holiday/sick/vacation time, and a bonus

Hours: Monday – Friday, 8a to 5p, CST or EST ONLY

Job Requirements

  • 2-3 years of executive assistant experience.
  • Superior organization skills and being detail-oriented are musts.
  • Bachelor’s degree preferred.
  • Good verbal/written/electronic communication skills, and an ability to effectively converse with management/C-Suite.
  • Conference / seminar experience preferred.
  • Technologically proficient with common office software, as well as online tools and platforms such as G-Suite, Kartra, Dubsado, etc. We are willing to teach someone on specific platforms, but you should be a fast, eager learner of new technology.

Job Type: Full-time, remote, W2

Education: Bachelor’s (Preferred)


Google Suite: 1 year (Required)
Administrative Experience: 1 year (Required)
Graphic design: 1 year (Preferred)
Kartra: 1 year (Preferred)

~ MUST Apply Through HireMyMom.com Website ONLY ~

Tagged as: administrative assistant, executive administrative assistant, OBM, online business manager, virtual assistant


About Ashley Kirkwood:

After graduating top of her class at Northwestern Law and going to trial around the country for Fortune 100 corporations, Ashley left her mid-six-figure salary to be a full-time entrepreneur. Now, Ashley runs both a law firm and a speaking business, where she speaks at colleges, conferences and corporations around the world delivering her signature speech, The Currency of Confidence!

Ashley has earned the nickname of “the lit lawyer” due to her fun DIY legal trainings such as Get The Tea On Trademarks and Clapback With Contracts. She is high-energy and dedicated to her clients’ success. Through her law firm, Mobile General Counsel, she helps entrepreneurs with critical elements of their business such as trademarks and contracts!

When Ashley speaks, crowds listen. She serves as a regular legal expert for a daytime talk show in Chicago. In addition, she travels the country speaking. So much so, that she was asked to help other speakers to do the same. Through Speak Your Way To Cash, her speaking business, Ashley coaches and trains emerging speakers on how to kick-start their speaking businesses! She hosts a podcast and a free Facebook group where she provides resources to speakers looking to start speaking their way to cash!