Some people stumble into their calling; others seem destined for it from the very beginning. Toni Jacaruso, Founder & President of Jacaruso Enterprises falls firmly in the latter category. Long before she became one of the most influential women in hospitality, she was already practicing leadership in her own neighborhood.

As a young girl, she ran a babysitting business that was anything but ordinary. Unlike most kids who simply took the occasional job, Toni thought bigger. She organized her friends, delegated assignments, and even took a small cut from each job to expand her reach. “I was basically a tiny CEO before I could even drive,” she laughs. What started as pocket money became her first lesson in entrepreneurship, teaching her the basics of leadership, money management, and teamwork.

By 16, she landed her first “real” job at the Holiday Inn in downtown Minneapolis. For most teenagers, it might have been just another part-time gig, but for Toni, it was life-changing. “That hands-on, gritty role hooked me on hospitality,” she recalls. “I got a front-row seat to how hotels actually run, and I loved every second of it.”

The Climb Through Hospitality

Fueled by this early passion, Toni pursued a degree in Hotel & Restaurant Management and later completed her MBA. Over the next two decades, she took on roles that gave her insight into nearly every part of hotel operations. She learned the mechanics of guest services, the intricacies of sales, and the high-stakes world of leadership.

Eventually, her hard work led her to the role of Vice President of Sales for a management and asset company, a coveted position that came with prestige and pressure in equal measure. For many, this would have been the pinnacle of success. For Toni, however, it became the stage for one of the hardest moments of her career. She was unexpectedly fired.

“Every setback in my career was really a setup for something greater. Being fired gave me the freedom to build what I truly believed in.”

“It was painful, humiliating, and honestly, it rocked me to my core,” she admits. “But as hard as it was, that moment became my turning point.”

The Napkin Epiphany

Sometimes, breakthroughs come in the unlikeliest of places. For Toni, it happened on the floor of an airport during a long layover. She had boarded a plane to visit her mother in St. John, U.S. Virgin Islands, still processing the abrupt end of her corporate career. With little more than a pen and a stack of airplane napkins, she began to map out her future.

“I wrote down everything: what I loved, what I didn’t, and what I would never do again,” she recalls. As she circled problems and drew arrows between ideas, one realization stood out: hotels were losing revenue not because of lack of opportunity, but because they couldn’t afford or find experienced sales talent.

The solution felt radical at the time: What if experienced professionals could plug in remotely and deliver results from day one? That insight became the blueprint for what would eventually grow into Jacaruso Enterprises.

By the time her layover ended, she wasn’t just unemployed anymore, she was an entrepreneur with a bold new idea that would reshape an entire industry.

Jacaruso Enterprises

Founded in 2007, Jacaruso Enterprises started small, scrappy, and remote from the very beginning. The company was built on a daring promise: to provide hotels with top-tier sales support without the constraints of location. For properties that couldn’t afford or attract local talent, Toni’s model was a lifeline.

“We gave hotels something they didn’t think was possible: access to experienced sales leaders from day one, no matter where they were located,” Toni explains.

Over the years, the company scaled with care. They built relationships, expanded services, and created a customized CRM system that gave hotel clients full visibility into results. From a handful of partners, Jacaruso Enterprises grew to serve thousands of hotels across the United States, Canada, the Caribbean, and Latin America.

The recognition soon followed, such as spots on the Inc. 5000 list of Fastest Growing Private Companies for multiple years and repeated Best Workplace awards. But for Toni, numbers tell only part of the story. “What I am most proud of is the culture we have built: mutual respect, continuous training, and people we genuinely want to vacation with,” she says warmly.

What started with a stack of napkins has grown into one of the most respected companies in the hospitality industry, proof that sometimes the lowest point in life becomes the start of the brightest chapter.

A Motto That Became a North Star

When Toni Jacaruso founded her company, she didn’t just want to build a business but a life she and others would love. Out of that vision came a simple but powerful motto that continues to define the company today:

“Do what you love, with people you love, and help others.”

For Toni, these words are more than a mantra, they’re a leadership philosophy. “If you love the work, energy and passion come naturally. If you love the people you work with, culture stays human. And when you’re committed to helping others, you stay grounded and useful,” she explains.

This philosophy shows up everywhere at Jacaruso Enterprises, from hiring decisions to day-to-day interactions. Toni often jokes that she only hires people she’d actually want to vacation with. But behind the humor lies a serious point: the right people are everything.

“Culture isn’t a perk or a poster on the wall. It’s the daily choice to show up for each other with respect, empathy, and energy.”

Redefining Hospitality Sales 

Before Jacaruso Enterprises, hotel sales followed a predictable model. A Director of Sales and their on-property team managed everything from guest rooms to events, meetings, and catering. Geography was destiny: a rural hotel in the Midwest couldn’t attract the same talent as a luxury property in New York.

Toni disrupted that model entirely. By offering remote hotel sales support, she erased geography as a limitation. Hotels no longer needed to worry about finding the perfect local hire, they could instantly tap into seasoned sales professionals who already knew how to deliver results.

“People were skeptical at first,” Toni recalls. “They wondered how someone living in Seattle could represent a hotel in rural Texas, or how we’d access systems remotely. But the results spoke louder than doubt.”

Her team invested in strong brand partnerships, technology, and a custom CRM that offered full transparency. Clients could see exactly what the Jacaruso team was doing on their behalf, from building group blocks to generating leads. Slowly but surely, the industry’s doubts faded, replaced by recognition that remote sales could not only work but often outperform traditional approaches.

Growth Fueled by People, Passion, and Innovation

Over time, Jacaruso Enterprises became known not only for its innovative model but also for its consistent results. Revenues soared past $20 million, and the company secured a place on the Inc. 5000 list for four consecutive years.

But ask Toni the secret to this growth, and she won’t talk about numbers first. She’ll talk about people.

“We never stop raising the bar, but we do it by focusing on outcomes and valuing people over profit,” she explains. “We look for individuals who are competitive, tenacious, and curious. Skills can be taught, but drive and attitude? That’s what sets our team apart.”

This people-first mindset is paired with a relentless commitment to innovation. Beyond their core services, Jacaruso has recently developed Lead Shark, a groundbreaking AI-powered platform that combines Jacaruso’s deep sales expertise with the most advanced intelligence to make prospecting, and market research and analysis faster and more precise.  

“The combination of impactful results, a people-first culture, and continuous innovation is what fuels our growth,” Toni says confidently.

Leadership Rooted in Authenticity

“Leadership is not about being the loudest in the room. It’s about listening deeply, acting with courage, and bringing out the best in those around you.”

Toni’s leadership style is often described as energetic and authentic. She doesn’t hide behind titles or layers of management. Every team member has her personal phone number, and she shows up to meetings with the same directness and enthusiasm that she expects from others.

“For me, leadership is about being clear, being prompt, and being human,” she says. Transparency is key: the company openly shares financials, discusses major decisions with the team, and encourages constant feedback. “We check egos at the door, reward curiosity, and practice empathy,” Toni adds.

Despite being fully remote, the culture feels remarkably connected. Regular virtual coffee chats, monthly meetings, and biannual in-person gatherings keep the team close-knit. Toni describes it as intentionality making the effort to ensure relationships are nurtured across screens.

“Even though we’re remote, our team feels more connected than some who work in the same building,” she says. “That’s not by accident, it’s by design.”

Resilience in the Face of Crisis

The true character of a company is revealed in tough times and for Jacaruso Enterprises, that test came during the pandemic. As travel came to a halt, and hotels everywhere faced unprecedented challenges, the very industry the company supported seemed to be collapsing.

But instead of retreating, Toni and her team leaned in. They worked tirelessly to generate new business that helped properties stay open and keep staff employed. “The most rewarding milestone of my career has been surviving and protecting our people through the pandemic,” Toni reflects. “Public recognition and awards are meaningful, but knowing we helped preserve livelihoods during the hardest time our industry has ever faced, that’s what I’ll never forget.”

For Toni, it was proof that her guiding motto wasn’t just words on paper. It was a way of leading through the darkest storm: with love for the work, care for the people beside her, and a commitment to helping others no matter what.

A Voice That Resonates Beyond the Boardroom

Toni Jacaruso is not only a leader within her company, she’s a voice that carries weight across the entire hospitality industry. Over the years, she has become a sought-after speaker for hospitality brands, conferences, and institutions. For her, these moments on stage are not about spotlight, but about dialogue.

“Speaking engagements keep us curious,” she explains. “We share strategies that are working for the countless hotels we support, but in return, audiences bring us fresh challenges and ideas.”

This exchange of ideas is what keeps her sharp. Each question from an audience member, each conversation with a hotelier, provides insight into the evolving landscape of hospitality. “Those conversations often shape the services we create, the training we deliver, and even the direction we take as a company,” Toni adds.

Her sessions are known for being honest, practical, and deeply relatable, a reflection of her authentic leadership style. She doesn’t sugarcoat the realities of the industry, but she always leaves her audience with a sense of possibility.

Technology That Empowers, Not Replaces

“Innovation in hospitality should never replace the human touch — it should free us to focus more on relationships.”

In a world rushing toward automation, Toni has a clear perspective: technology should empower people, not replace them. After all, Jacaruso Enterprises has always been ahead of the curve. They built a remote-first company in 2007, long before “remote work” became a trend.

Now, they’re doubling down on innovation with platforms like Lead Shark, which blends artificial intelligence with the company’s deep sales knowledge. By automating time-consuming tasks like prospecting, Lead Shark allows sales professionals to focus on what they do best: building relationships and closing business.

“The future of hospitality will be driven by innovations that make hotels smarter, faster, and more human. AI can create efficiency, but human connection is what wins deals. That balance is non-negotiable.”

Beyond sales, she also highlights other innovations shaping the future of hospitality like sustainability initiatives, contactless services, and personalization. These, she believes, will continue to influence how guests choose hotels and how properties build loyalty.

Inclusivity and the Power of Example

As a woman leading in a male-dominated field, Toni understands the importance of representation. But she doesn’t see her influence as limited to titles or achievements. Instead, she focuses on daily actions.

“I try to be the leader I wished I had: visible, practical, and unapologetically ambitious,” she explains. She mentors other women, ensures female voices are heard at every level of her organization, and shows that success doesn’t require sacrificing compassion.

“You don’t have to choose between caring for people and driving performance. Both matter,” she says firmly.

Her advice to aspiring women leaders is simple but powerful: “Ask for help often, trust your instincts, and surround yourself with people who will tell you the truth. Failure isn’t the enemy, it’s part of the process. Learn loudly, adjust quickly, and keep going.”

A Vision for 2025 and Beyond

Looking ahead, Toni sees the next chapter of Jacaruso Enterprises as one of smarter growth and global expansion. As of October, she has stepped into a new role as President, passing the CEO title to Jason Webb, while her husband and business partner, Bill Jacaruso, continues as COO. Together with a strong executive team, the company plans to expand internationally, launch new services, and prepare for the public release of Lead Shark in 2026.

“My vision is to grow smarter, not just bigger,” Toni says. The strategy is to remain the premier partner for remote sales while scaling training and technology that uplift entire hotel teams. The company is committed to preserving the culture that has always been its backbone while embracing the changes shaping the industry.

“We know guest expectations will continue to evolve, and technology will keep advancing at lightning speed,” she reflects. “Our job is to stay ahead of that curve while staying grounded in our values.”

A Legacy of Impact and Empowerment

“I don’t measure success in dollars. I measure it in the lives we’ve changed, the people we’ve helped, and the teams we’ve lifted up.”

When asked about her legacy, Toni doesn’t talk about awards or revenue milestones. Instead, she talks about people.

“My greatest reward has been hearing team members say their lives are better because they worked at Jacaruso,” she shares. Whether that means more confidence, better work-life balance, or the joy of being part of a supportive culture, those stories mean the world to her.

For the industry, she hopes her work leaves behind options. She envisions a future where no hotel has to lose revenue because of its location, and where remote sales is seen as a proven, respected path to growth.

And for women leaders everywhere, her legacy is one of possibility. “If I can show that it’s possible to succeed without compromising who you are, I know others will feel empowered to do the same,” she says.

In the end, Toni Jacaruso hopes to be remembered not just for building a successful company, but for inspiring people to do work they love, with people they love, while helping others. For her, it has always been about creating deep relationships, living life with purpose, and inspiring others to do the same. “If Jacaruso is remembered as the place where people found joy in their work, built meaningful relationships, and made a positive impact in the lives of others, that would be the legacy I’m most proud of.”

“When I look back, what matters most isn’t the size of the company we built, it’s the culture that gave people connection, laughter, and a true sense of belonging.”