Rising Stars: Meet Jessica Cliff of Olmsted Falls

Today we’d like to introduce you to Jessica Cliff.

Hi Jessica, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
Our entrepreneurial story wasn’t sparked by a single event, but rather by a unique opportunity that felt meant to be. My partners, Craig and Daniel, attended culinary school together years ago, and all of us have extensive experience as entrepreneurs. This foundation allowed us to recognize the potential in acquiring this business and building something truly special together. Since taking over, we’ve had countless meaningful moments with our community, our partnership, and our staff. It’s been incredibly rewarding to get to know our regulars and feel so welcomed into the Olmsted Falls community. However, the most significant milestone is quickly approaching: our one-year anniversary of ownership at the end of October. This milestone represents a successful first year of honoring the restaurant’s legacy while pouring our own hearts into making it a place we and our community can be proud of.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Absolutely not smooth—and we’ve only been open a year! The first year is less of a road and more of a sprint. Everything is happening at once, and you have to solve problems on the fly.

Our main struggles have been the typical, high-intensity ones that hit any new restaurant: the long, intense hours required just to get things off the ground, and the persistent challenge of staff turnover. We are constantly training, finding great people, and working to build the kind of culture that makes them want to stay.

On top of that, we’ve had the added challenge of defining our roles within the new partnership. We were friends with a shared vision, but learning to effectively communicate, divide responsibilities, and trust each other’s decisions under pressure has been a huge part of the learning curve.

Ultimately, these struggles haven’t broken us; they’ve simply served as a very intense training course that proved our team—and our partnership—is strong enough to handle anything.

Can you tell our readers more about what you do and what you think sets you apart from others?
As a partnership, the vision for Matteo’s is clear: we aim to be Olmsted Falls’ go-to spot for authentic, scratch-made Italian comfort food.

Our specialization lies in combining the discipline of a scratch kitchen—meaning we make our sauces, dressings, and many other items in-house—with a local first mentality. We are known for our commitment to quality, which means sourcing as much product locally as possible, ensuring the freshest ingredients in every dish. We truly pride ourselves on creating food that is both authentic Italian cuisine and deeply comforting.

What I’m most proud of is the atmosphere and the team culture we’ve built. We’re a new restaurant, and creating a truly warm, professional, and welcoming environment takes focused effort. I’m proud of our staff for quickly establishing Matteo’s as an extension of our guests’ own dining rooms.

What sets us apart is this dedication to service and hospitality combined with our local roots. Craig & Daniel ensure the food is phenomenal—and it is. My job is to ensure the service matches that quality. We want guests to feel at home the moment they step in. When you combine our scratch-kitchen philosophy with a truly attentive, neighborhood-focused Front of House experience, and the fact that all the owners live right here in Olmsted Falls and have kids in the local schools, that’s what makes Matteo’s Casual Italian truly stand out.

Do you have recommendations for books, apps, blogs, etc?
Absolutely. Since our top priority is being a cohesive team, we’re always focused on learning and communicating better. We use a multi-platform approach to development.

To improve internal communication, we’ve taken personality quizzes and we regularly enroll in extended training through the Chamber of Commerce. We even read business books together as a leadership group to ensure we’re all aligned on our strategy.

Individually, we each have our preferred method of staying sharp: I personally follow Dave Ramsey’s business blogs for leadership insights; Daniel is a fan of podcasts; and Craig keeps up with industry trends by following other successful restaurant owners on social media.

We treat this constant learning as an essential part of our operation. If any one of us runs across a good article or tip—whether it’s about business strategy or service excellence—we immediately share it in our group chat. It ensures we’re not just serving great food, but we’re also operating with the sharpest possible teamwork.

Contact Info:

• Website: https://www.matteoscleveland.com
• Instagram: https://www.instagram.com/matteos_olmsted_falls
• Facebook: https://www.facebook.com/matteoscleveland