Alyssa Calhoun

Chief Operating Officer

Alyssa@pearlplanning.com | 734.274.6744

A woman with shoulder-length wavy blonde hair, wearing a light blue blazer, white top, black pants, and white high heels, sitting on a black bench against a neutral background, smiling at the camera.

BACKGROUND

At Pearl Planning, our core values set the rhythm of our work, and as Chief Operating Officer and Integrator, I make sure they show up every day. I turn our vision into reality, keep our operations, systems, and partnerships running smoothly, clear roadblocks early, and make sure our team has what they need to do their best work. That care carries through to every client, who can count on a smooth, personal experience from their first conversation onward. Because when we live our values, our team thrives and so do our clients.

I started out as a nanny and household manager for several families, including Melissa Joy’s. It taught me that trust, organization, and personal connection make everything else work. When Melissa founded Pearl Planning, she welcomed me onto the team as a client service representative, and I’ve loved growing alongside the firm ever since.

Dexter has been home for more than 20 years. It’s where my husband, Ryan, and I met in high school, and where we’re now raising our two daughters, Myla and Briar, in the community that helped shape us. There’s something special about building a life in the place where it all began.

Get to know Alyssa

YOU MIGHT BUMP INTO ME

At the park with my girls, wandering the aisles of Target, or tackling the next DIY house project.

A QUOTE ON MY DESK

"All our dreams can come true, if we have the courage to pursue them." - Walt Disney

THREE FAVORITE WORDS

Kindness, Trust, Clarity

THE TEAM

Meet the rest of the Pearl team