Toni Jacaruso

Revolutionizing Hotel Sales

In the fast-paced world of travel and hospitality, innovation is the name of the game. Pioneers and trailblazers lead the way, reshaping the industry for the better. In this exclusive interview, we delve into the inspiring journey of Toni Jacaruso, the visionary founder of Jacaruso Enterprises, Inc. Based in Round Rock, Texas, this groundbreaking company has redefined the traditional model of hotel sales services.

From a childhood marked by an entrepreneurial spirit to the inception of an innovative remote sales service, Toni’s story is a testament to the power of determination and innovation in the ever-evolving world of travel and hospitality. In this exclusive interview we explored her journey, her company’s mission, and the remarkable impact it has had on the hotel industry.

Give us a brief overview of your background and your journey since the beginning of your career.

Since my childhood, I’ve had an entrepreneurial spirit. Early on, I established a neighborhood babysitting business that I expanded successfully by hiring my friends as my “employees” and taking a cut of their pay.

As soon as I was old enough, I got a job at a Holiday Inn in downtown Minneapolis. This kicked off a 20 +year career in the hospitality industry that advanced concurrently with my undergraduate studies in Hotel & Restaurant Management, followed by an MBA. I worked hard and earned director-level positions for some of the largest hotel brands in the world before moving into a role as Vice President of Sales for a hotel management and asset company with annual revenues close to a billion dollars. But I noticed something was missing both in my career and in the hospitality industry.

So, I started a company that introduced a groundbreaking concept: remote hotel sales service. Today, I remain profoundly thankful for the 100+ dedicated individuals who choose to work alongside me. Their contributions are instrumental in fostering the culture of mutual respect that has led to our collective success.

What inspired you to start Jacaruso Enterprises? Can you provide a detailed overview of your organization’s services and its mission & objectives in serving the hotel industry?

In the traditional hotel sales model, sales activities are overseen by an on-site Director of Sales, leading a team of sales managers, catering managers, and sales coordinators. Their primary focus is to drive hotel revenue by selling sleeping rooms, special events, meetings, conventions, food & beverage, and special amenities such as spa services, packages, or leisure activities. Until 2007, this was all handled in-house, on-site, hotel by hotel.

When I was inspired to start a company, I believed it was possible to do what I loved, with people I loved, and to help others.  Spurred on by the wide adoption of SaaS and rapid explosion of mobile technology, Jacaruso Enterprises pioneered a new way of working in hotel sales. Our highly experienced, all-remote, distributed workforce leverages technology to engage with customers and co-workers. Our clients get the benefit of a trained sales expert, ready on day one to start bringing new business into the hotel, all at a fraction of the cost of hiring and training an on-site employee.

Our service carved out a unique niche in the hotel industry and has opened hundreds of new doors for branded hotels and boutique properties throughout the US, Canada, the Caribbean and Latin America. We’ve achieved growth by assembling an exceptional team of experts dedicated to one another and the hotels we serve. Jacaruso Enterprises has earned a spot on the Inc. 5000 list of Fastest Growing Private Companies in America from 2017 to 2021 and has recently been recognized as one of the Inc. 5000 Best Workplaces in 2023. With a workforce of 115 employees and over 800 hotel partners, we’ve spent over 16 years in business continually innovating to meet our customers’ ever-evolving needs in the dynamic hospitality landscape.

How do you tailor your services to meet the unique needs of different types of hotels? Can you share some success stories or case studies of hotels that have seen significant improvements after using your sales services?

More than 3,500 hotels in the U.S, Canada and Latin America have relied on Jacaruso services including ongoing sales outsourcing, short-term support of a specific property, or sales training. Rather than offering a one-size-fits all solution, we build a relationship with each hotel and its own set of requirements and challenges. We work closely with most of our hotel clients on an ongoing basis, becoming a trusted collaborator with their on-site team. We are known for our deep hotel sales expertise that we tailor to meet the unique needs of our clients and their various types of hotels.

We have countless success stories of hotels that use our service. In 2022, our partnering hotels saw over $269M in direct revenue contributions. Some of the testimonials I’m most proud of come from two of our current customers:

“Working with Jacaruso has been one of the best decisions we made for our hotel. We can focus on operations while Jacaruso drives revenue. We know we are in great hands!” -Kaylan A., Vermont

“Jacaruso helped open our hotel in 2020, and we continue to lead the market in occupancy because of their services. Hiring them has been the best decision we have made.” -Neal S., New York

What were the primal challenges and roadblocks you faced during the initial phase? And what is your source of motivation?

My last job before starting my company was highly visible, lucrative, stressful, and unfulfilling. Incessant management of crisis after crisis prevented me from reflecting on what it was that I really wanted to do.

Shortly after leaving that position, I found myself in an airport in the Caribbean with 4-hour layover. Armed with nothing but airplane napkins, I sat down on the terminal floor and began to write. An hour later, looking at a mosaic of napkins sprawled before me, I had the ideas for the inception of Jacaruso Enterprises.

When you’re setting out to establish an innovative service or product, there’s no established path to follow. But there are those who’ve navigated similar terrain. I’ve built a network of fellow entrepreneurs who generously share their experiences, help me sidestep pitfalls, and give me access to resources that help me overcome hurdles.

The most valuable lesson I’ve gleaned is that you should never underestimate the impact of hiring extraordinary employees. Even during the peak of the pandemic, when travel was at a standstill, our exceptional team united to create a network that collectively generated leads for all the hotels we supported. Our employees successfully secured millions of dollars in new business that preserved jobs and kept our hotels afloat.

Today, I remain profoundly thankful for the 100+ dedicated individuals who choose to work alongside me. Their contributions are instrumental in fostering a culture of mutual respect and motivation. I’m both humbled by and in awe of our collective success.

What sets Jacaruso Enterprises apart from competitors? How do you strategize your game plans to tackle competition in the market?

We acknowledge that we have competitors. Even though we have more competitors now than we did pre-pandemic, our primary focus remains on innovating our services so that we provide maximum value to our partner hotels and propel the industry forward. Some of the advantages that set us apart are our extensive network, our exceptional team, and our extended track record of results.

Within each major hotel brand, we have cultivated long-term partnerships and established vital connections with high-level stakeholders and decision makers. Our meticulous hiring process and comprehensive benefits preserve the company culture and attract top talent to our team. The expertise and unwavering commitment of our employees consistently drive results for our partner hotels. We track these results with our cutting-edge technology, which delivers interactive reports to each customer, detailing their return on investment.

How do you stay ahead of industry trends and adapt your services to meet customer demands? Have there been any recent trends or changes in the hotel industry that have had a significant impact on your organization’s approach to sales services?

It’s important to stay in the know about what’s going on in our industry. We do this in a variety of ways including:

Continuous Learning: Our team actively engages in ongoing learning via participation in industry events, conferences, training programs and our bi-annual in-person company meeting to stay updated on the latest trends, technologies, and best practices in hotel sales and the hospitality industry. We keep a close eye on trends and changes within the hotel industry, such as shifts in guest preferences, the impact of global events (like the COVID-19 pandemic), and advances in automation, digital marketing, and more.

Market Analysis: We have an internal research team that conducts in-depth market analysis for our partner hotels and the state of hospitality to help us understand current market dynamics, competitor strategies, and emerging trends. This information allows us to adjust our services accordingly in response to changes in the marketplace.

Technology Integration: We are constantly staying at the forefront of emerging technology. Our digital technology team helps us to leverages cutting-edge tools and software to streamline our sales efforts and gather valuable data insights. We use this data to tailor our strategies and identify areas for improvement. Our CRM platform is completely customized which allows us to share the most impactful information to our hotel partners.

Recent shifts in the hotel industry such as the growing use of automation, labor shortage, and the widespread adoption of artificial intelligence (AI), have significantly influenced our operations for the better. Earlier this year, we developed a new remote sales service that provides two sales experts for one price to help hotels get further faster. This dynamic sales duo provides hotels with a comprehensive proactive and reactive effort that can complement or substitute an onsite sales team. The integration of automation and AI for our team has improved our efficiency, allowing us to get more work done in less time. We are also on the verge of introducing new tools and technologies with automation and AI, promising further advancements in our services.

Brief us about the current industry scenario and what was the impact of covid-19 pandemic on hospitality Industry?

The industry has had its share of trying times, but nothing like the last few years. 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. The industry as a whole has truly bounced back, but many markets are still in recovery. People are traveling again; jobs are returning and new opportunities are available every day. There’s a lot of momentum right now and we’re maximizing it. What we’ve continued to see is a hyper-focus on health and safety of guests, enhanced cleaning protocols, evolving digital communication, shorter travel booking windows and an increase in the use of automation as well as AI.

In your opinion, what are the key factors that contribute to the success of a hospitality company/Hotels? Can you share any upcoming trends or innovations that you believe will shape the industry in the near future?

Exceptional guest experience: Providing an outstanding guest experience is critical. From the moment a guest enters the property to the time they check out, every interaction should be seamless, enjoyable, and memorable.

Effective sales (and marketing!) effort: Successful hotels have robust sales and marketing strategies in place to ensure their rooms are filled. A strong online presence, use of market analytics, and a targeted sales effort are essential to staying competitive.

Adaptability and innovation: The hospitality industry is ever evolving. Hotels must be adaptable and embrace innovations. Trends like contactless check-ins, sustainable practices, and the use of technology for guest services are now the standard for travelers. These innovations continue to shape the industry.

As for upcoming trends and innovations, we anticipate several developments shaping the industry in the near future such as:

Artificial Intelligence (AI): AI is transforming the way hotels operate, engage with guests, and make data-driven decisions. It has allowed us to create highly personalized guest experiences like identifying guest preferences, from room temperature and lighting to food and entertainment choices. Chatbots and virtual assistants are also enhancing guest interactions. Some hotels even have robots deliver fresh towels to your door. AI is continually being used in revenue management to analyze a wide range of data, including historical booking patterns, market demand, competitor pricing and predictive analytics. We’re starting to see the use of voice and facial recognition more, contactless check in, check out and so many more ways to leverage AI. It’s not slowing down any time soon.

Sustainability: Environmental sustainability will continue to gain significance, with a growing emphasis on reducing waste, energy efficiency, and sustainable sourcing of materials.

Personalization: Guests are seeking personalized experiences. Hotels will use data analytics and AI to tailor services, offers, and amenities to individual preferences.

Remote Services: As seen with remote sales services, more hotels will embrace remote or virtual solutions for various aspects, such as general assistance, concierge services, and meetings. It’s proven that remote services help with expediting hiring, and often can be more cost effective.

What key milestones have you set for your company for 2024? Where do you see yourself in the near future and what are your future goals?

In 2024, our primary focus revolves around achieving significant milestones that align with our mission to support hoteliers and their ever-evolving needs. We are committed to further expanding our service offerings to better cater to the dynamic landscape of the hospitality industry. We are developing new services that will be meticulously crafted to enhance our partner hotels’ capabilities and empower them to thrive in a competitive market.

A central goal for 2024 is the continued growth of our hotel portfolio. We aim to extend our reach and impact by partnering with a wider array of hotels, ranging from established brands to boutique and independent properties. Our remote sales services have consistently proven to be instrumental in driving revenue for hotels, and in the coming year, we plan to make this invaluable resource accessible to even more properties.

Looking beyond 2024, we envision a future where Jacaruso Enterprises plays a pivotal role in the success of numerous hotels across diverse markets. We are committed to fostering strong, enduring partnerships with our clients, assisting them in achieving their revenue and sales goals. Our overarching goal remains to be at the forefront of innovative solutions in the hospitality industry, continually adapting to meet evolving needs of hoteliers and making a lasting impact.

Provide one-line quote that best describes your approach to business and your vision.

I founded JE based on the vision of “do what you love, with people you love, and help others”.

Do what you love – If you love what you do, energy and passion come naturally.

With people you love – We only hire people we want to vacation with. We have a greater sense of purpose, because we’re in this together.

Help others- When someone asks for help, we honor their humility, so no one ever feels alone

What are the key qualities and skills you believe are necessary for a successful entrepreneur?

Here are some key qualities and skills I believe are necessary for a successful entrepreneur:

Have fun: The ability to have fun in your role and create a relaxed and enjoyable work atmosphere goes a long way. Don’t take yourself too seriously. Belly laughs are good for the soul.

Hire people smarter than you: I encourage entrepreneurs to recruit top-tier industry professionals who are unequivocally talented and often smarter than themselves. Hiring a team of experts can contribute to the success of your venture and help you get further faster.

Always use crystal clear communication: Set clear goals and expectations for the team. Leave no room for misinterpretation.

Lead by example: Demonstrate the desired behaviors and skills through your personal actions and behavior.

Master relationship building: Building strong, meaningful relationships with team members and clients is critical. People want to work with and buy from people they like and trust.

Be committed to learning: Actively seek opportunities that will help you to continuously learn and expand your expertise. Keep up with industry trends and best practices. Be hungry for knowledge.

Embrace technology: Be open to embracing and utilizing new technologies for enhanced efficiency and effectiveness.

These qualities and skills can pave the way to success. Embrace them!

What advice would you have for someone thinking of entering this space right now? What would you advise to the budding entrepreneurs in general?

My advice to aspiring entrepreneurs is to ask for help often, don’t blindly follow advice, and trust your instincts. When people told me my ideas wouldn’t work, I’d never earn enough money to retire, and employees wouldn’t leave a job with a known entity to work for a start-up, I replied, “Watch me.” I also rely on a small circle of close friends who love me enough to tell me the truth.


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