Meet Two Of The Most Important Women In The Richest Jamaican-Born CEO’s Life

While accepting her Golden Globe award for best actress in a TV musical or comedy last year, actress Ayo Edebiri did something so rare it became headline news. She thanked “the people who answer her crazy emails” also known as her agent and manager’s assistants.

While a “thank you” may be rare to hear coming from someone who benefitted from your labor, the American Society of Administrative Professionals (ASAP) says, “administrative assistants are often the unsung heroes of the workplace and serve as the backbone of office success.”

Just ask Bailey Medical Equipment & Supplies and Pharmacy Founder and richest Jamaican-born woman, Dr. Trisha Bailey how she manages the day-to-day operations of 16 businesses and life as a mother of five children. She knows the importance of having the right people around.

After being in a coma for eight days following a suicide attempt and then left alone sitting in a wheelchair waiting to board her connecting flight back to Florida, an airport staffer came to help her. She said she remembers feeling invisible that day, so she decided to launch Bailey’s Medical Equipment & Supplies.

Now the self-made billionaire and author has an executive team, hundreds of staffers and two women who work together as her chief of staff, Jessica Dyson, and personal assistant, Pete-Ann Burke Barrett.

“Collectively, Jessica and Pete-Ann are the two best assistants anyone could ask for,” she said. “Pete-Ann’s loyalty to ensure I’m at my best daily keeps me sharp.”

Trisha said Jessica’s dedication to self-improvement and the growth of the company is unparalleled.

“Together, they are truly two of the most remarkable people I’ve ever met, and I thank God for bringing them into my life,” she said.

In 2015, Jessica started working as an intake coordinator doing data entry for the Trisha’s growing company. She was able to learn so many things juggling different tasks. After a year on the job, she got the opportunity to become Trisha’s personal assistant after a vacancy came open. Jessica said she finds herself doing things she never imagined, such as working alongside other senior-level staffers and stakeholders in the company, traveling the country and speaking in front of 200+ people at company wide meetings.

“I learned that I can figure things out and it’s rewarding to have someone put that much trust in you and guide you,” she said. “I’m still not sure how my name got recommended for the assistant position but it did and I haven’t looked back. Dr. Bailey’s superpower is making leaders out of people and bringing their best qualities out.”

For Trisha, the feeling is mutual.

“Jessica’s ability to focus on any given task is unparalleled,” she said. “She truly exemplifies what it means to be my right hand. Her ability to adapt to new environments and learn new information independently sets her apart from others, placing her among the elite tier of executives.”

Just like Trisha, Pete-Ann’s life started in Jamaica. She said she had her heart set on working in the medical field as a neurosurgeon and even worked at a law firm before migrating to the United States. Once she arrived in the United States, she landed an entry-level job working at Bailey Medical’s before moving to NYC for a few years. Eventually, Jessica found herself knocking on the doors that she left open at Bailey’s Medical and rejoined the company in 2019.

For Trisha, Pete-Ann’s strengths lie in the creative space, where she has the ability to “transform anything or anyone from ordinary to stunning.”

“Her skills are incredibly multifaceted, spanning real estate, design, perfecting my makeup, and seamlessly transitioning to leading staff,” she said. “Pete-Ann’s feistiness and zest for perfection push me to excel in everything I do.”

Both women agree that finding the balance between anticipating someone else’s needs and figuring things out on your own is crucial to be successful in their types of jobs. 

Jessica and Pete-Ann agreed they have both learned to set boundaries in their roles, so that they can take time for self-care and to recharge and still have their own set of goals.

They also have a boss “that knows boundaries and  how to give and take with them,” Jessica said.

“We make sure to spend valuable time pouring into our own families by laughing and putting away our phones when we come back home after days away of on work-related travel,” Pete-Ann said.

Just like their boss who is a former UCONN track star, Jessica and Pete-Ann have taken up a new hobby as a form of self-care. They trained and both finished a 5K together this past December. Just like they do on most days – right besides each other to get the job done.