Alyssa Calhoun

Operations Manager & Integrator

Background

Supporting people and creating structure have always been at the core of what I do — it’s how I bring clarity, lift others up, and keep things moving forward. I started my career as a nanny and household manager for several families, including Melissa Joy's, learning trust, organization, and personal connection. That experience evolved into something even more meaningful when Melissa founded Pearl Planning in 2018 and welcomed me onto the team as a client service representative. I’ve been proud to grow alongside the firm ever since.

Today, as Operations Manager & Integrator, I focus on keeping our day-to-day operations running smoothly. I’m committed to supporting our team by removing roadblocks, responding to challenges, and ensuring everyone has what they need to do their best work. I also help ensure that everything we do reflects our core values, creating a positive, people-first environment. Playing a key role in the rhythm that helps our firm—and our clients—thrive is what makes this work so fulfilling.

Dexter has been home for over 20 years and holds a special place in our hearts. It’s where my husband, Ryan, and I first met back in high school, and now we’re raising our two daughters, Myla and Briar, in the same community that helped shape who we are. There’s something truly meaningful about building a life where it all began and sharing that foundation with our girls.