20 Influential Leaders Which Everyone Should Know in 2021: Toni Jacaruso

Global Business Leaders Magazine
A leader efficiently and powerfully scaling the company to new heights


“When they fired me, I was stunned to realize the immediate relief I felt.” Toni Jacaruso, Founder, and CEO of Jacaruso Enterprises built a multi-million-dollar company on 3 driving principles: do what you love, with people you love, and help others. Jacaruso Enterprises provides remote sales support and training to hotels in the US, Canada, the Caribbean, and Latin America.

1. Can you help us understand the current scenario in the hospitality industry? How has it changed in recent times?

The industry has had its share of trying times, but nothing like the past year. The US travel economy experienced a $492 billion loss at the height of the pandemic. We saw 3.1 million jobs vanish and thousands of hotels close their doors. It was devastating. Fast forward to today, and the vaccine has restored hope. People are traveling again, and jobs are returning. The hospitality industry is slowly but surely recovering. We will continue to see a  hyper-focus on the health and safety of guests, enhanced cleaning protocols, evolving digital communication, and shorter travel booking windows.

2. Please briefly tell us about Jacaruso. What inspired you to establish the company? Also, can you please help walk us through the services?

I had an eye-opening experience after getting fired. Contemplating my next steps, I began crafting the foundation of Jacaruso Enterprises. Our company has been built on 3 driving principles: do what you love, with people you love, and help others.

We are a team of hotel experts who are passionate about sales. Since our start in 2007, we have become the most innovative hotel sales services company in the world. Our core service, remote hotel sales support, provides hotels all the benefits of having an onsite salesperson for less than half the cost. We find hotel travelers in the market, set up accounts through RFPs, and ensure every incoming lead gets a response. We also provide preopening sales for new hotels, short-term sales support for hotels with a vacancy in their sales office, as well as virtual sales and operations training.

3. Please tell us about your entrepreneurial journey. What are some achievements and highlights from your career?

After building several successful neighborhood businesses, I was finally old enough to get “a real job.” I went to work as a night auditor at a Holiday Inn in downtown Minneapolis. I quickly developed aspirations of being promoted to sales manager, primarily because salespeople didn’t have to wear a uniform or a nametag!

My entrepreneurial traits were already in full force by then, such as a disregard for roadblocks and a high tolerance for risk. I approached the Director of Sales at the hotel and asked if she would allow me to work in the sales office while the current salesperson was out on leave. She scrutinized me for a moment and then asked, “Can you type?” I replied   with one word: “Yes.” She acquiesced, offering me the temporary position and telling me that I would be expected to start on Monday. It was Thursday. After work that day, I jumped in the car and raced to the community college to enroll in a typing class so that I could learn to type over the weekend.

My hotel journey continued for the next 20 years. I held positions at the director level for some of the largest hotel franchise companies in the world, culminating in my last job as the Vice President of Sales for a hotel management and asset company with annual revenues close to a billion dollars. Unfortunately, I hated the work. I was running so fast from project to project, problem to problem, I didn’t realize I wasn’t happy. My life was out of balance and the company’s core values were not close to my own. When they fired me, I was stunned by the immediate relief I felt.

A few weeks later, I boarded a plane to visit my mom in St. John, USVI. I found myself with a 4-hour layover in San Juan. With that time to think, a creative spark flickered that had been dormant for the past several years. I plopped down on the carpet in an empty gate area and started writing feverishly on a stack of airplane napkins. An hour later, my hand was sore, my hair was a mess, and before me was a beautiful napkin mosaic consisting of 3 sections: things I love to do, things I like to do, and things I will never do again! And just like that, Jacaruso Enterprises was born.

I am grateful for the people who choose to work for me and who foster a culture of mutual respect. I am humbled by our success. For the last 5 years, Jacaruso Enterprises has been on the Inc. 5000 list of fastest-growing private companies. In 2019, we worked with 68 different hotels brands, supported over 900 hotels in North & South America, employed over 150 people, and topped annual revenue of over $18 million. In 2020,  we were ranked in the Inc. 5000 Best Workplaces and were recognized by CEO World Awards, Corporate Excellence Awards, various associations as well as peers from the largest hotel companies in the world.

4. As a leader of the company, how do you motivate your team members, especially during these difficult times?

During a difficult time, people need reassurance, hope, and comfort. They also need the truth. I communicate clearly and often. As CEO, it is my job to make the tough calls and deliver the tough messages, but with transparent communication, my team can make the best decisions for themselves.

5. Failures are part of the entrepreneurial journey. How do you handle failures? What are the different lessons you have learned?

As an entrepreneur and a visionary, I have had more business ideas fail than succeed. From these failures, I have learned about humility, and I try to extend grace as often as possible. I  have learned that I would rather try and fail than not try at all. I don’t have any regrets about my failed business ventures, but I would have had regrets about not starting them. Lastly, I’ve learned that when I fail and fail BIG, I always end up in a better place than when I started because then I have experience to bring to my next venture or to share with someone else.

6. Please share some of your favorite client reviews/testimonials which inspired you to keep going.

Since 2007, our hotel sales services have opened new doors for major hotels and boutique properties throughout the US, Canada, the Caribbean and Latin America. We’ve had hundreds of client testimonials that have inspired me. Their comments especially lifted my spirits over the past year when there was a lot of uncertainty in the world. I’ll share a recent testimonial that sums up our value as a business well, from Aly El-Bassuni, now Chief Operation Officer at Yugo: “Hotel owners ask me all the time what to do to help generate revenue at their hotels. We chose to partner with Jacaruso to help our teams drive results and increase profitability. Their hotel sales support is best-in-class and their Accelerate eLearning is exactly what hotel teams need to generate revenue.”

7. What other hobbies or interests do you share beyond the cabin? How do they help in honing your leadership skills?

My favorite hobby is my involvement in Entrepreneurs’ Organization (EO), a global peer-to-peer network of entrepreneurs. I have a big appetite for learning and EO feeds that hunger. Our Austin chapter has some of the most brilliant-minded people I have ever met. Some of my best leadership skills have come from listening to the experience of other entrepreneurs.

8. Which fictional/non-fictional character has been a source of influence to you and why?

The first character that came to mind was Katniss Everdeen, the fictional protagonist of The Hunger Games.  Katniss is brave, even when she is afraid. She finds a way to prevail, even when it looks bleak. She is loyal to the people she loves. She uses her mind to come up with clever strategies to win.

9. “20 Influential Leaders Which Everyone Should Know in 2021,” features the leaders who have exceptional qualities to lead their What are the unique leadership qualities that you possess?

My leadership style is like my personality: driven, competitive, and compassionate. I don’t want anyone to have to guess what I am thinking or what I expect. Although I am opinionated about all aspects of my business, I express those opinions with respect, gratitude, and decisiveness. I started my business like most entrepreneurs I know – with $5,000 and a guest room for an office. When my revenues grew, I began to narrow hiring decisions to once clear criterion: only hire people I   want to go on vacation with. That way I will always be surrounded in my business by people I love. So far, it’s working!

Toni Jacaruso, CEO of Jacaruso Enterprises
September 9, 2021

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