Jacaruso Enterprises: A Company Built on Heart, Hustle, and a Burst of Clarity
Many companies are born in boardrooms. This one began in an airport terminal.
The year was 2007. Founder Toni Jacaruso had just been let go from a high-powered job and was hit with the kind of professional heartbreak that has a way of stripping life down to its sharpest edges. Sitting at her gate, waiting to fly home to her mother, she reached for whatever she had nearby: a stack of airplane napkins. And she started writing. She wrote what she loved. What she didn’t. What she would never do again. Somewhere between frustration and relief, a simple idea came to her that would transform her career.
Do what you love, with people you love, while helping others.
There was no big strategy at first. No roadmap. Just a woman deciding to rebuild her life around purpose rather than pressure. The remote hotel sales model developed over time. The culture came immediately. And everything Jacaruso Enterprises is today – the thousands of hotels supported, the loyal client base, the team that feels like a family – trace back to that moment on those napkins.
The company is now led by a new CEO who guards that founding philosophy fiercely. Jason Webb, who has been with the company since 2012, is the first CEO other than the owner and President, Toni Jacaruso. He is passionate about building great teams, creating lasting solutions, and helping Jacaruso’s hotel partners succeed. His commitment is to ensure that Toni’s dream continues to survive growth, competition, and the industry’s nonstop pace.
“We want people to do their best work because they feel seen, heard, and valued,” Webb says. “That’s how we help our hotel partners win. Everything begins with culture.”
A Culture Built First — and Protected Always
Ask anyone inside Jacaruso what makes the company different, and they’ll point to the same thing every time: the people. Not the tools. Not the model. The people.
The company began as a remote team long before remote work became the norm, which meant trust had to be earned quickly and communication had to be intentional.
So connection was built into the company’s daily life. Coffee chats. Wellness check-ins. A holiday gift exchange. Spirit week. Real conversations about career wins and real conversations about life kids, partners, struggles, the stuff that follows us beyond our laptops.
Twice a year, the whole team meets in person. There are hugs. Laughter. The kind of easy familiarity that happens when people honestly care about one another. The gatherings are more than corporate retreats. They’re reminders that behind every sales call and every report, there’s a human being doing their best work.
When someone hits a wall, support arrives fast. When someone succeeds, the whole team cheers. When a partner needs help, people step in before being asked. That culture doesn’t just feel good. It fuels performance. It’s the heartbeat of the company and the hardest thing for competitors to copy.
What Really Sets Jacaruso Apart in a Crowded Field
There’s no shortage of remote hospitality service providers now, especially after the pandemic forced the industry to rethink nearly everything. But Jacaruso’s edge isn’t hidden — it’s right out in the open in differentiators like these.
The team is wildly experienced. On average, Jacaruso salespeople bring more than 12 years of hotel sales expertise to their roles. They operate like an extension of the hotel’s own staff – reliable, proactive, and invested.
The systems run deeper. Internal networks, brand relationships, custom CRM reporting, tools built specifically for hotel environments – all of it gives hotels an advantage most providers can’t offer.
And then there’s Lead Shark.
Jacaruso’s AI-powered intelligence tool is designed specifically for hotel sales. It’s not an adapted CRM, not a generic prospecting platform. Lead Shark was built from scratch because nothing on the market could do the job right. It will change the way hotel salespeople find the right contacts, the speed at which deals move, and the accuracy of targeting — all without erasing the human touch.
Competitors can imitate the idea of remote hotel sales. They can’t recreate the relationships, the technology, the intuition, or the culture that make Jacaruso’s version work.
Remote Hotel Sales Before Remote Was A Thing
In creating a company based on a remote workforce, Toni didn’t set out to be ahead of the curve. She just understood the reality of hotel work. When you’re on property, distractions never stop. A front desk question here, a guest problem there, and entire days vanish without a single sales call made.
She believed that removing the noise would unleash better selling. Time, focus, consistency were the ingredients. Remote work wasn’t a trend. It was simply the smartest way to get results.
Years later, the pandemic unintentionally validated her model. Remote sales became the backbone of hotel revenue during shutdowns. Other companies rushed in. Competition exploded tenfold. But instead of fighting noise with more noise, Jacaruso doubled down on what made them strong: people, clarity, innovation, and results.
That discipline led to new tools, new systems, and eventually to Lead Shark, a product no one else saw coming.
The Stories That Matter Most
Ask Toni for her favorite success story, and she’ll hesitate, not because there aren’t many, but because the best ones aren’t flashy.
A hotel owner finally breathing again because revenue is stable.
A GM saying sales aren’t a worry anymore.
A team member telling her that working at this company gave them balance they never thought possible.
These are the moments that stick. The quiet wins. The relief in someone’s voice. The feeling of stability after months of strain.
Results matter, of course. But the stories behind them, the lives steadied, the teams supported, that’s the part no spreadsheet can track.
Looking Forward: A Future Built on People and Smarter Tools
The next few years are shaping up to be transformative with Jason at the helm as CEO. Lead Shark’s 2026 launch will open a new chapter in hotel sales intelligence. Global expansion is underway. New services are being built to help hotels manage staffing gaps and fluctuating demand. Internal systems are being strengthened so growth never dilutes quality.
And through all of this, one priority is non-negotiable:
Protect the culture Toni built.
Technology will make the work faster.
Systems will make the work cleaner.
But the human element will stay at the center of everything.
What the Founder Hopes People Say a Decade from Now
Ten years from now, she hopes the story is simple:
That Jacaruso made life easier for hotel owners.
That partners felt supported.
That revenue grew when times were tough.
That the company brought stability, clarity, and peace of mind.
That team members felt valued and changed for the better.
And that the industry is stronger because of the ideas and people Jacaruso put into the world.
If that happens, then the clarity brought about by those napkin scribbles in that airport years ago will have done more than start a company, they will have shaped an entire corner of the hospitality industry.
Company Name : Jacaruso Enterprises, Inc
Website: https://jacaruso.com/
Management Team
Jason Webb | Chief Executive Officer
