Mark Holzberg, CEO, Cloud5 Communications, tells what time in tech has taught him so far.
What is the achievement in business you’re most proud of?
One of the accomplishments I am most proud of is spearheading Cloud5’s evolution as a trusted partner to thousands of hotels amongst the leading brands and management companies.
We’ve created an organization that makes complicated IT environments dramatically easier for our clients to manage so that they can achieve their technology objectives and continue to satisfy their guests. We’ve worked hand-in-hand with our customers to deliver innovative, customer-centric solutions that yield quantifiable results.
From voice and Internet solutions to Contact Center operations and managed IT services, Cloud5 is now synonymous with reliability, service excellence and hospitality technology expertise. What is more fulfilling is the feedback that we get from our customers. They appreciate our collaborative spirit and our ability to evolve and innovate in this rapidly transforming sector. They know that they can depend on us and that is highly rewarding.
What first made you think of a career in technology?
It wasn’t intentional. After doing a stint on active duty in the army, I was waiting to go to law school. In the meantime, I took a job and got involved in mergers and acquisitions. We acquired Western Union, which had a new travel division that supplied technology and connectivity for airline reservation systems and travel agencies, and I just happened to run that business unit for a while. I enjoyed it and I was good at it – my future at law school went by the wayside.
What style of management philosophy do you employ with direct reports as CEO?
I believe in transparency, collaboration and accountability – bringing those three things together in terms of a culture is how I work with my direct reports and operate as a leadership team at Cloud5.
What is the current hot technology that you’re anticipating to impact your industry?
I get asked about AI a lot and while AI certainly impacts our business and we use AI tools, it’s not so much about having the next best thing for us – it’s about enabling the best things for the customers we support.
In fact, I call what we do the “plumbing” – the infrastructure that makes everything else function. For us, it’s about continuing to deliver a strong backbone that can facilitate new technologies that are important to our clients along with the support necessary for all the technology that goes into a hotel today.
Our focus is on being that critical infrastructure and technology support partner that makes all the other innovations possible.
How do you deal with stress and unwind outside the office?
I’ve been in this business for years and there is always stress. You just learn to live with it – in fact for me, the absence of stress would be a bit stressful. Having said that, I do Pilates and play pickleball to relax. I’m also about to marry a wonderful woman who is truly my partner and having her in my life makes a huge difference.
If you could go back and change one career decision, what would it be?
I wouldn’t have done anything radically differently. I’ve grown from all the mistakes and victories I have made along the way – and each experience has moulded me into the individual and leader I am today.
What do you currently identify as the major areas of investment in your industry?
Broadly, having the appropriate technology stack that yields efficiencies is where I see people are investing. At Cloud5, we’re focused on our MSP and IT services business because we view the marketplace demand growing exponentially, so we’re investing time and dollars for organic development and M&A in that area.
What are the industry-specific challenges when implementing new technologies in hospitality?
A clear definition of what ‘problem’ is being solved for is very important due to the complex stakeholder landscape of our industry – from property owners to management companies to brands to the actual guests. Poor alignment between stakeholders on intended results leads to unsatisfactory outcomes. Success is only possible with adequate planning and through defining clear goals prior to initiating development.
What changes to your job role have you seen in the last year and how do you see these developing in the next 12 months?
We started 2025 off with a pretty strong economy. Hospitality did well the last couple of years and was returning to normal. But all that has been turned upside down. I was recently emailing our ownership about where things were going. I told them I’ve got lines on my face for every turn of the business cycle over the last 30 years. I have deep grooves for some of them, including 9/11, the Great Recession and COVID. I was expecting what we’re going through now with Tariffs to be just one of those lines. But those lines may be turning into crevices too.
So, while I’ll continue focusing on growing and diversifying the business, I’m now looking at contingencies if the economy takes a huge hit due to the global tariffs and the geopolitical situation.
What advice would you offer somebody aspiring to obtain a C-level position in your industry? What about others entering the field of hospitality?
Everyone says to do something you like, but I think you also need to do something you can be good at. Your attributes, strengths and skill sets need to be put into a field where you can excel. I believe being inquisitive, curious and willing to learn is important. You also need to be good at dealing with and managing people.
Knowledge of both the tech side and hospitality is a benefit for those going into this industry specifically.
Our business sits at the crossroads of guest experience and technology infrastructure, so being able to speak both languages will set you apart.
