In an industry known for fast change, Donald OGrady has chosen to stay put and rise through the ranks at his employer of almost two decades.

After completing an undergraduate degree in Business Administration with a concentration in Information Technology, OGrady joined Kimpton Hotels & Restaurants as an IT Manager in 2007, where he was responsible for all systems and support for a 417-room hotel. OGrady was then promoted to a regional IT management role, director of property technology post, and regional vice president of property technology before assuming his current role as VP of technology. In it, he directs an enterprise-wide technology team, including strategy and budgets. His responsibilities extend to security, property technology, applications, data center, support, and new acquisitions.

HC: What does a typical day at work look like for you?

OGrady: My time is usually divided between project calls, meetings within my team, and working with other departments here at Kimpton. I have four direct reports, who are all senior director level, and oversee the departments that make up my team: Openings & Transitions, Enterprise Systems (including Data Center), Business Solutions/Operations (including Helpdesk), and Property Technology.

HC: You’ve been with Kimpton for a while. What attracted you to the company and hospitality in general?

OGrady: I’ve always enjoyed travel and I worked a few hotel jobs while I was in college. There’s a certain buzz you can get from working at a Front Desk. Through that experience, I know it’s a challenging job to be an operator, and supporting our teams is still something I find rewarding. 

HC: What has kept you at Kimpton and in hospitality? What are the perks/benefits to the industry or this particular hotel company in general?

OGrady: I’ve been extremely fortunate to land at a company that is completely focused on creating great experiences for our guests. That clarity of purpose makes it easy to align all of our efforts. What’s just as important for me is the Kimpton culture which encourages, and expects, all of us to be our authentic, unique selves.  

HC: What are your top tips for rising up the ranks in the hospitality industry?

OGrady: Create your own path: Identify a role that fulfills a current or future need for your team or your company and then present yourself as the solution – and do the math to justify it. Then do the same for others to create opportunities for them as well. Take advantage of any available soft-skills training offered by your company. Those are the skills that will get you to the next level.

HC: What traits separate those IT employees from others who are able to succeed in management positions?

OGrady: I tell my team to hire IT staff who would make good Front Desk agents. Technology, like hospitality, is essentially a service business – our goal is to provide services that are valued by customers. So it’s not surprising that those who are successful in tech management start with a drive to provide great service.

HC: What are the unique challenges of IT work in hospitality and of your day-to-day job?

OGrady: I’ve encountered experienced techies who come to this industry assuming they’re comfortable with the 24/7 nature of our business because they pulled occasional weekend, on-call duty. As someone who has worked many graveyard shifts at hotels, I appreciate that our staff – and our guests – need our full support around the clock. Because our priority is always the guest experience, it can be challenging to make the case for technology initiatives that don’t directly support that process. At a financial institution, the product is the data and the systems that provide and protect it are undeniably essential. In hospitality, I sometimes need to connect the dots to make that case.  

HC: How do you feel about the overall job market for Tech professionals in hospitality right now?

OGrady: Hotels and restaurants are becoming increasingly complex computing environments as additional guest-facing services are being added (and secured). Management companies and owners are beginning to realize that supporting these interconnected systems, and leveraging them for their full value requires more technology staff than it has in the past – and that this is a somewhat specialized skill set.

HC: Where are the hiring needs?

OGrady: I see a lot of opportunities for IT Technician/Manager positions at the property level. That role is a great starting point to going deeper (into a particular technology area) or broader (into IT management) because you learn both the business and the technology.

HC: What skills or experiences are most in demand in the hospitality job market for tech?

OGrady: Both security and project management experience are very valuable right now. If you have both, you won’t go hungry any time soon.

HC: What advice can you offer those tech professionals who are interested in breaking in to hospitality?

OGrady: I’m inclined to flip this question and offer advice to hospitality staff who want to break into technology. My advice is: “Join us.” Leverage your operational experience and apply your existing technical aptitude to an IT role. You can pick up the technical certifications you need along the way, but your business knowledge will be even more valuable. Some of our most successful people on the Kimpton Technology team started in hotel or restaurant operations.

HC: What kind of educational background/credentials would you recommend to those interested in an IT job at a hotel?

OGrady: Technology evolves faster than business. So in that sense, I tend to place more value on current technical certifications for specific IT skills and look at the degree to add more context and depth. The PMP (Project Management Professional) is a good one to add because it demonstrates, if nothing else, that someone can follow a rigid preparation process and pass a truly arduous exam.

HC: How helpful has the business administration degree been?

OGrady: This has become more valuable as my key relationships have increasingly included owners and asset managers. Being able to understand their priorities and speak their language is more important than translating three-letter acronyms.

HC: What types of experience and expectations are required for those in more senior-level positions, such as yours?

OGrady: Our field has an inevitable “knowledge inversion” where the manager will always know less than those they manage because the technology keeps changing. One of the most difficult challenges IT staff face, when they are promoted, is “letting go” – giving up the hands-on technical work that got them where they are. The ability to recognize this and to shift from tactical solutions to strategic planning is critical in moving into more senior-level positions.

HC: What is the income potential for senior-level IT professionals in hospitality and at your level?

OGrady: I’m actually paid in Bitcoin so it’s difficult to do the conversion. In all seriousness, IT pros with the right set of skills and experience will find the compensation competitive with other industries – and you get all the free pens you want.