More Selling Power. Less Friction.

How Jacaruso Enterprises Is Building What Today’s Hotel Teams Actually Need

Hotel teams do not have a shortage of things to do. They have properties to operate, guests to take care of, teams to lead, revenue goals to hit, accounts to grow and new business to find. At the same time, they are managing systems, answering emails, solving operational issues and being asked to produce more with fewer resources.

Jacaruso Enterprises has had a front-row seat to that evolution for nearly two decades. Founded in 2007 by Toni Jacaruso, the company built its foundation in remote hotel sales long before flexible work became commonplace. Today, under the leadership of CEO Jason Webb, Jacaruso has expanded well beyond its original model, giving hotels access to sales expertise, strategic support, interim and pre-opening resources, training and technology designed around the realities of hospitality.

The solutions have evolved because hotels have evolved.

“Remote sales today cannot just mean doing the same job from somewhere else,” says April Eskelson, Vice President of Bold Moves at Jacaruso Enterprises. “Hotels are leaner. GMs are wearing more hats. Ownership groups expect clearer results. Sales teams need better information, stronger follow-through and more flexibility than they did even a few years ago.”

For Jacaruso, that changing environment has created a much bigger opportunity than simply providing an alternative to an onsite salesperson. It has challenged the company to keep asking a better question: What does this hotel actually need to create more selling power?

Sometimes the answer is additional sales activity. Sometimes it is experienced leadership. Sometimes it is help uncovering new accounts, stronger follow-up, temporary coverage during a transition or expertise leading into a hotel opening. Increasingly, it can also mean giving an existing team better tools to do the job.

Start With the Problem, Not the Headcount

When a hotel needs more revenue, the instinct is often straightforward: hire another salesperson. Sometimes that is exactly the right answer. But Jacaruso has learned that the underlying problem is not always headcount.

A hotel may have talented people who simply do not have enough time to consistently look for new business. Another property may need higher-level sales expertise without needing that resource onsite every day. A management company may need scalable sales support across an entire portfolio. A brand may need an experienced partner that understands how to support hotels consistently across different markets. And a new opening may need sales expertise months before the doors ever open.

“The question is not always, ‘Who else can we hire?’” Eskelson says. “It is, ‘How do we create more selling power with the resources we already have?’”

That distinction has helped shape the Jacaruso model. Its remote sales support has grown to include strategic sales leadership, account development, administrative support, interim coverage, pre-opening support and technology that helps sellers find opportunities faster. Rather than forcing every hotel into the same solution, those resources allow owners, management companies and hotel teams to address the gaps that are actually standing between them and more revenue.

That approach has been tested at scale. Today, Jacaruso supports more than 800 hotels across more than 69 brands and has supported more than 5,500 hotels throughout its history, including more than 750 pre-openings. That breadth gives the company visibility into what is happening across brands, markets, ownership structures and hotel types. The lessons shaping its services are not theoretical. They come from thousands of hotels and nearly two decades spent inside the realities of hotel sales.

The results are measurable, too. In the first quarter of 2026 alone, Jacaruso’s hotel sales service generated more than $93 million in revenue across the 800-plus hotels it supports. It is an important distinction: remote sales is not simply a solution for filling a staffing gap. Done well, it is a revenue strategy.

The goal is not simply more activity. It is better activity, in the right places, with the right expertise behind it.

There Is More Business Out There

That same thinking eventually helped create Lead Shark. Originally developed as an internal Jacaruso resource, Lead Shark grew from a problem the company knew well: hotel salespeople can spend an enormous amount of time trying to figure out where to look before they ever begin selling.

Researching companies, searching for contacts, understanding what is happening in a market and determining whether an account is actually worth pursuing all take time. Lead Shark was created to shorten the distance between searching and selling.

Since making the AI-powered platform available to the wider hotel industry, Jacaruso has learned something surprisingly simple.

“Hoteliers do not want another place to search,” Eskelson says. “They want to know where the business is.”

Lead Shark helps hotel teams analyze their market, surface potential accounts, understand why an opportunity matters, identify the right decision-makers and move into outreach faster. But the bigger story is what happens when a hotel sees something it did not know was there.

Sometimes the opportunity is only a few miles away. A company expands. A new construction project begins. A crew starts traveling into the market. A local business creates recurring room-night demand. An account that has historically stayed somewhere else suddenly has a new need. The demand may already exist; the hotel simply has to know where to look, who to call and why the opportunity matters.

“That is the part I love,” Eskelson says. “Lead Shark is not about giving someone more data. It is about helping them see opportunity they were missing.”

That opportunity has already translated into real dollars. Lead Shark has uncovered more than $3.8 million in revenue opportunities for hotels, reinforcing the idea that the most valuable lead is often not one that has to be created from scratch. It is one that was already there and simply had not been found yet.

Then the human part begins. Technology can help a salesperson uncover the opportunity, understand it and get to the right person faster. It cannot replace the curiosity, conversation, follow-up and trust that turn an opportunity into an account.

That distinction matters deeply to Jacaruso. The company is not using technology to remove people from hotel sales. It is using technology to remove some of the friction that keeps good salespeople from spending enough time actually selling.

Training Has to Survive Monday Morning

The same philosophy shows up in another growing part of Jacaruso: training.

Eskelson, who leads Bold Moves, has spent more than 20 years in hotel sales, leadership, training and innovation. After years of watching hospitality professionals sit through workshops, conferences and training sessions, she does not believe the industry has an information problem.

“We have an application problem,” she says.

A training session can be inspiring. The room can be energized and everyone can leave with pages of notes. Then Monday morning happens. The emails start. Someone calls out. A guest needs something. Revenue needs attention. The day takes over. If nothing changes in the way someone sells, leads, communicates or works afterward, the training did not do enough.

That is why Jacaruso approaches training much like it approaches hotel sales: start with the reality people are actually facing. Its programs use real hotel scenarios, real sales conversations and real leadership challenges, with learning experiences spanning sales, lead generation, leadership, service, revenue and artificial intelligence. The emphasis is not on giving people more information to remember. It is on giving them something useful to do next.

“I would rather give someone three things they will actually use than thirty things they will forget before they get back to the hotel,” Eskelson says. “The goal is not to impress the room. The goal is to change what happens after everyone leaves it.”

That focus has become increasingly relevant as hotel teams are expected to adapt faster. New technology alone does not make a team more effective. Neither does a one-time training event that disappears the minute everyone returns to work. Jacaruso’s approach connects the two: give people better resources, then make sure they know how to put them to work in the real situations they face every day.

Different Solutions. One Very Human Business.

At first glance, remote sales, an AI prospecting platform and hospitality training may look like very different solutions. Inside Jacaruso, they are connected by the same idea: make it easier for people to do the work that produces results.

Lead Shark reduces the time a salesperson spends digging for information. Remote sales gives a hotel access to experience, capacity and expertise that may not exist on property. Training gives hospitality professionals practical ways to sell, lead and work more effectively.

None of those things matter if they lose sight of the relationships underneath them.

“The best innovation does not remove the human part of hospitality,” Eskelson says. “It creates more room for it.”

That philosophy has remained remarkably consistent even as Jacaruso itself has grown. The way hotels buy, operate, staff and sell has changed considerably since 2007. The company’s answer has never been to hold onto a model simply because it worked before. It has continued adding resources around the challenges its hotel partners are actually experiencing, while keeping the relationship-driven approach that built the company in the first place.

Nearly two decades after Jacaruso Enterprises began selling hotels remotely, the tools are more sophisticated, the services are broader and the hotel industry looks very different. What hotels need from their partners has changed with it.

They need people who know how to sell. They need better ways to uncover opportunities. They need expertise they can access when and where they need it. They need training that changes what happens when everyone gets back to work. And they need technology that helps great people become even better at what only people can do.

Jacaruso has spent nearly 20 years learning those lessons alongside the hotels it serves. Now, it is putting all of them to work.

If you’re ready to make Mondays suck less, contact Jacaruso