Meet Your Strategic Sidekick

A woman with brown hair, wearing glasses and a nose ring, smiling at the beach with wavy water in the background.

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

With extensive experience in executive support, operations management, and project implementation, I am 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 day to day and stay focused on what matters most.

I’m not just a virtual assistant or a consultant. I’m a proactive problem solver, a thought partner, and a trusted collaborator. I genuinely care about the humans behind the business.

Meet My Team

  • 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

What I Bring to the Table

A cozy-but-confident approach to organizing the messy middle

The emotional intelligence to support your team and leadership

A sharp eye for detail and a big picture mindset

A knack for turning vague visions into actionable roadmaps

A love of structure, strategy, and smooth operations

More About Me

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. I first started working there at 15 years old invoicing, pulling parts, and packing up boxes to send across the country. Every afternoon I drove to work and stamped my 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.

Before launching my own business, I spent over 8 years in Nashville working in restaurant management and real estate operations, two fast-paced, people-heavy industries that taught me how to juggle a thousand things at once, keep my cool under pressure, and find systems in the chaos.

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!

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.