Meet Your Strategic Sidekick

A woman with glasses and earrings smiling while holding a stack of books against a plain background.

Hi, I’m Ashleigh Phifer, founder of Sidekick Operations, and your go-to partner for turning operational chaos into calm clarity.

I’m proud to help growing businesses build better systems, streamline their day to day, and reclaim time to do what they love.

I started Sidekick Operations because I believe that every passionate business owner deserves a reliable, strategic support system. Someone who can help them untangle the chaos and stay focused on what matters most.

I’m a proactive problem solver, a thought partner, and a trusted collaborator. I genuinely care about the humans behind the business.

A smiling woman and man wearing glasses, close together, in a restaurant or cafe setting.

My Story

Tennessee-born, Kentucky-based, and proudly operating as the chaos taming sidekick behind Sidekick Operations.

I’ve always had a love for small business and entrepreneurship. I grew up in our family owned business, spending my days after school watching cartoons on the tv in the office and running around the warehouse shelves full of marine parts. My first solo venture was at 8 years old when I would take over the supplies closet to set up a pretend store to sell everyone office supplies under the table. All that free inventory for the taking! I thought I was a genius.

I started actually working there at 15 - invoicing, pulling parts in the warehouse, and packing up boxes to send across the country. Every day after school I drove to work and stamped my little paper time card to clock in. I think back on that and know that watching my grandma, grandpa, dad, and mom work together to provide for us and build something great is the foundation for who I am today.

Now I live just outside of Cincinnati in Northern Kentucky with my amazing boyfriend and our two sweet dogs: Chloe, the independent diva, and Monkey, the cuddlebug with a big personality.

My approach to business (and life) is grounded in kindness, curiosity, and clarity. I believe systems don’t have to be cold and support should always feel human. If you’re looking for someone who can bring strategy and heart to your business I’d love to be your Sidekick.

Ashleigh learning computer basics at an early age

Little me first learning how to use a computer. The rest is history!

My Sidekicks

  • Close-up of a dog with a tan and white coat, sitting on a black car seat, wearing a colorful woven collar.

    Chloe Josephine

    DIRECTOR OF SNIFFING

  • Close-up of a small black and tan dog with pointy ears, lying on a textured gray blanket, looking up at the camera.

    Monkey Louise

    DIRECTOR OF SNACKING

Contact me

If you’re looking for a thoughtful, resourceful partner to help you get clear, get organized, and grow intentionally, you’ve found your sidekick.