Virginia CEOs Stories: Tom Rosser of Gelati Celesti – The Challenge of Leading a Family Business Into Its Next Generation

When most people think of Gelati Celesti, they think about ice cream. Tom Rosser thinks about succession, leadership, and building a company that can thrive long after he’s no longer sitting in the president’s chair.

As president of Gelati Celesti, Tom leads a business that has become a Virginia institution. The company operates 11 scoop shops, a food truck, and a production facility, receiving raw ingredients, manufacturing its own ice cream, distributing it to stores, and serving customers directly. While it’s a highly sophisticated operation, the mission remains simple: create moments of joy.

“In a world where people are constantly hit with bad news, it’s nice to provide a place where people can disconnect, spend time with friends and family, and enjoy a little treat,” Tom says. That mission shows up every day in the stores. According to Tom, most customers arrive happy, and nearly everyone leaves that way. “There’s always that one percent,” he jokes, “but for the other 99%, we get to be part of a good moment in their day.”

From Founder to Family Business

The Gelati Celesti story began in 1984 when founder Peter Edmonds opened the company’s first location in Richmond. In 2010, Tom’s parents, Steve and Kim Rosser, acquired the business and began writing the next chapter. Steve led the company for more than a decade before retiring in 2023, creating a transition that many family businesses eventually face but few navigate easily.

By then, the next generation was already involved. Tom’s sister joined the company in 2018, and Tom followed in 2022. After Steve’s retirement, the siblings initially stepped into leadership as co-presidents together before Tom became president in 2025 while his sister moved into a part-time ownership and creative leadership role following the birth of her first child.

When asked what accomplishment he’s most proud of, Tom doesn’t mention growth, expansion, or financial results. Instead, he points to the leadership transition itself.

The Leadership Transition That Didn’t Break the Company

Moving from a first-generation leader to a second-generation leader can create instability. Reporting structures change, institutional knowledge walks out the door, and employees naturally wonder whether the culture and strategy will change with it. Tom expected the transition to be difficult.

“I thought it was going to be a pretty rough transition period,” he says. “But we were able to transition leadership without losing members of the leadership team, and nobody felt misaligned with where the family or the business was going.”

That outcome didn’t happen by accident. The family invested significant time into succession planning and governance work, including bringing in outside advisors to help formalize structures and facilitate important conversations. Tom says he would strongly recommend that kind of work to any family business. Successful succession isn’t really about transferring authority. It’s about preserving trust throughout the organization while creating clarity around what comes next.

The Challenge After Succession

The transition may be complete, but Tom believes the harder question is what comes afterward.

“Everybody is here. Everybody is ready. Everybody is poised. Where are we going?”

That’s the challenge occupying much of his attention today. With leadership settled and the organization stable, his focus has shifted toward defining Gelati Celesti’s next stage of growth. That means aligning family stakeholders around a long-term vision, developing strategy, and helping every department understand how its goals connect to the overall direction of the company. Tom has begun incorporating principles from EOS (Entrepreneurial Operating System) to help create that alignment, but he is also navigating another reality: this is his first time leading a company.

“I haven’t led a company before,” he says. “Everything I do is brand new.”

Many leaders feel pressure to project certainty in every situation. Tom is comfortable acknowledging that leadership is learned through experience, mentorship, and making decisions before you feel fully prepared. That’s one reason he values both coaching and the perspective of fellow business owners.

Learning From Other Leaders

As a member of Virginia CEOs Roundtable 5, Tom has found a group of leaders who have already experienced many of the challenges he’s facing for the first time. The businesses represented around the table may look completely different, but the underlying leadership issues are often surprisingly similar. Many members are second-generation business owners themselves, and their experience has become a valuable resource as Tom navigates his first CEO role.

“Between those eight people, they’ve pretty much seen every sort of problem,” he says. Whether it’s a people issue, growth challenge, or strategic decision, someone in the room has usually faced a version of it before. “When you start looking at the fundamentals, we’ve all got the same problems,” he says. “Most of them are people problems.”

The experience sharing, perspective, and collective wisdom have helped accelerate his growth as a leader and provided reassurance that many challenges are simply part of the CEO journey.

Building a Family-First Culture

Tom’s personal values show up clearly in the company’s culture. One area where he’s been especially intentional is flexibility. Rather than focusing on where people work or whether they’re physically sitting at a desk during specific hours, he prefers to focus on results and accountability.

“We don’t need everyone sitting in their seat from nine to five-thirty every day.”

Employees are encouraged to attend a child’s orchestra concert, step away for a school event, or handle important family responsibilities, provided they remain accountable for their commitments. Tom believes that approach creates a healthier workplace while strengthening trust between leaders and team members.

For a growing company, it’s also become a meaningful retention tool. Gelati Celesti doesn’t have unlimited resources, but flexibility is something the business can offer consistently. “The ability to offer time is really powerful for us,” Tom says. Creating a family-first environment has helped the company retain good people while building a culture that reflects the values of the ownership team.

How Tom Defines Success

Many CEOs define success through revenue growth, new locations, or market expansion. Tom’s definition is different. He believes success means building a company that no longer depends on him.

“I want to make myself replaceable.”

His goal is to create systems, processes, and leaders that allow Gelati Celesti to continue operating successfully whether he’s in the office or not. He doesn’t want the business to become dependent on a single individual, including the president. “I don’t want it to be Tom’s company,” he says. “It’s Gelati Celesti.”

That philosophy influences how he develops leaders, delegates responsibility, and thinks about long-term sustainability. It also connects directly to the life he wants outside of work. Success means being able to attend his daughter’s school events, spend meaningful time with family, and enjoy the moments that matter without feeling tethered to the business every hour of the day.

“I want to be able to look up and smell the roses.”

The Leadership Tool He Once Doubted

One practice has accelerated Tom’s growth as a leader more than almost anything else: coaching.

For the past several years, he’s worked with a professional coach every other week. Their conversations cover everything from leadership style and communication challenges to conflict management and interpersonal dynamics. At first, Tom wasn’t convinced it would be worthwhile.

“I kind of rolled my eyes at it. I thought, who needs a coach?”

Over time, his perspective changed completely. The more trust developed, the more valuable the conversations became. “The more vulnerable you get, the better the coaching gets,” he says.

One lesson in particular? “Clear is kind.”

The coaching relationship helped him become more comfortable with difficult conversations and less conflict-averse as a leader. It also gave him a dedicated space to focus on personal growth, something many CEOs rarely prioritize. Tom sees coaching and a peer group as serving different but complementary purposes. A coach helps him understand himself, while fellow business owners provide hard-earned experience from their own leadership journeys.

What’s Next for Gelati Celesti?

Today, Gelati Celesti operates seven locations in Richmond and four in Virginia Beach, but Tom continues to explore growth opportunities. He has spent several years searching for the right location in Northern Virginia and has also become increasingly interested in North Carolina’s Research Triangle region.

The opportunity is appealing because it would allow the company to continue manufacturing in Richmond while expanding into a fast-growing market within driving distance. At the same time, Tom isn’t interested in expanding simply for the sake of growth. The focus remains finding locations that fit the company’s culture, operating model, and long-term vision.

He’s also excited about developing new traditions around the brand. One upcoming initiative is a “Just Ask Week” centered around Gelati Celesti’s most popular flavor, complete with special offerings and community give-back efforts. It’s another example of how the company continues to evolve while staying rooted in the customer experience that made it successful in the first place.

A Fun Fact About Tom

Most people know Tom as the president of an ice cream company. What many don’t know is that he’s also the primary cook in his household.

“My wife can’t cook to save her life,” he says with a laugh.

Tom handles nearly all the cooking at home and enjoys experimenting with everything from stir-fries and French-inspired dishes to steakhouse classics. More than anything, cooking provides a way to disconnect from work and focus entirely on the task in front of him. It’s creative, hands-on, and refreshingly simple.

In a way, it’s not all that different from what Gelati Celesti provides its customers every day: a chance to slow down, enjoy the moment, and find a little joy in the middle of a busy life.


A big thank you to Tom for sharing his story with us. His openness about succession, leadership, coaching, family business governance, and company culture reflects the vulnerability and commitment to growth that makes the Virginia CEOs community work.

The Virginia CEOs Stories series highlights the leaders behind Virginia’s most impactful businesses and organizations. Through their successes, setbacks, and lessons learned, these stories remind us that growth rarely happens alone.

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