In this episode I’m interviewing Toni Jacaruso, a brilliant businesswoman with a sharp eye for a big idea, and a quick draw for making tough decisions. After spending seven days with us at a Birthing of Giants Fellowship week, Toni pulled the trigger on her plan to revitalize her company’s management team.

Toni founded Jacaruso Enterprises about 10 years ago, after spotting a huge problem in the hospitality industry. Unbeknownst to us hotel guests, most of the familiar hotel chains are actually locally owned franchises. Staffing is handled by each hotel individually, and more often than not, on-site salespeople are skipped altogether.

“What we found out in doing research,” Toni explained, “is over 50% of branded hotels do not have salespeople on site.”

With no dedicated salesperson in place, requests for negotiated rates or group bookings tend to get pushed to a hotel manager’s voicemail, where they quickly get lost or receive inexperienced attention. It’s a huge gap that a lot of business disappears into. With her substantial 15 years of experience working in the hospitality space, Toni stepped in to create a company that filled the breach.

Small Companies Solving Problems for Big Companies

Jacaruso Enterprises provides sales support to hotels and hotel chains nationwide. Toni gathers together top-notch salespeople who handle sales, negotiation, and prospect management for their clients regionally. Those salespeople are supported by regional directors, and a strong management team layered all the way up to the Austin headquarters. So now, when the phone rings with a sales call, Toni’s team is there to answer with the expertise and urgency needed to close the deal.

Toni’s company fits into one of the most successful business models that an entrepreneur can utilize. She started a small company that solved a problem big companies had. It’s a classic idea that has launched more successful businesses than any other. Jacaruso Enterprises is no exception.

A Booming Business

Ten years have passed since Toni founded her company, and business couldn’t be better. Jacaruso Enterprises now has over 60 different hotel brands as clients, is over 100 employees strong, and pulled in $8 million in revenue last year. Their growth is so remarkable that they made the Inc. 5000 list for the past 2 years. According to Toni, her business generates a lot of referrals from happy clients, and the renewal rate is very high.

“We have had unprecedented growth this year. So [I] just could not be happier with the growth that we’re seeing.”

Toni discovered, however, that with the unprecedented growth came an increase in work and responsibilities. It was beginning to tax her busy management network, and the team quickly found themselves being pulled away from the roles they performed best at. This was the problem that Toni took with her to a Birthing of Giants Fellowship week in July 2018.

An Upgrade To Management 2.0

Toni had surrounded herself with some of the strongest salespeople in the nation. They formed the core of her team at Jacaruso Enterprises. They helped bring her company to its current level of success; however, Tony had even bigger plans for her company. She knew that her current management team wasn’t properly positioned to help her achieve her dreams. It was time for something we talk about a lot here at Birthing of Giants: Management 2.0.

Entrepreneurs must never stop refining the talent in their company. Even when you’re certain that you have some of the best people in place, your management team has to develop and grow in response to a growth in revenue and clients. Sometimes that means bringing new people to the team. Sometimes it means moving existing team members around into slightly different roles. Toni needed both.

True to Toni’s natural quick start entrepreneurial style, once she decided that her management team needed expansion, she pulled the trigger on her plan within weeks of returning to Austin! The changes she made included promoting four people internally into VP and senior VP spots, adding two new VPs to the team, and hiring on three more Sales Directors. In the weeks that followed Toni added even more Sales Directors, all regionally placed to ensure great local coverage for her clients. She calls it Management 2.1, or maybe 2.2. Creating the perfect management team is a fluid process that takes time to get right.

The takeaway here is that you can’t scale your business, you can’t take your company to the next level if you don’t take on the overall strength and quality of your management team. Toni did it. She did it fast. She did it Toni style. Now that’s a fast draw.

Check out my extended interview with Toni Jacaruso on

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Lewis Schiff is the author of Business Brilliant: Surprising Lessons From the Greatest Self-Made Business Icons, the executive director of the Business Owners Council and the co-founder (with Norm Brodsky) of BEN Global Mentorship that helps business owners transform their companies into scalable enterprises and, eventually, enduring institutions with help from rockstar entrepreneurs from around the world.