Meet Mindsight’s VP Of Operations, Dana Bailey


August 14, 2018 by Siobhan Climer

Dana Bailey, Mindsight’s VP of Operations, sat down with Siobhan Climer, Mindsight’s Science and Technology Writer, to discuss his role in developing strategic operational and business objectives that transfer to the customer-centric focus for which Mindsight is known. Without Dana’s thoughtful insights into how our business can best serve our customers, Mindsight wouldn’t be able to deliver superior managed IT services and technological expertise.

Though Dana started out interested in marketing and communications, both a first job and a strategic mind put him on the path to becoming a business leader. Today, Dana manages both the project and service teams at Mindsight, works as part of the leadership team to ensure we are prepared to meet our clients’ evolving needs, and guides operations and strategy so Mindsight can continue being a leader in our industry.


vp of operations


What Does A VP Of Operations Do?


SC: A VP of Operations is described as everything from strategic planners to advanced HR directors. What do you see as your role here at Mindsight?

DB: One of the things that makes my role unique is I get to wear several different hats. I’ve been in business for over 32 years now, and I appreciate the opportunity to leverage my experiences in executive leadership across sales, marketing, and operations to help Mindsight continue to drive forward as a business. First off, we have a tremendous pool of engineering resources. The team is really comprised of two key functions: one is the service delivery function and the other is the project engineering function. Within those areas, I have to provide a lot of focus. This is a 24/7/365 operation. A lot of the stuff we’re managing every day is mission-critical for our customers. We have a team and processes that we ensure are structured and capable to handle what we’re doing today and is scalable for what we’ll be doing tomorrow. And that’s a lot of what I focus on.

vp of operations

I focus on process. I focus on how work flows in the team, and how – within that team – resources can be leveraged to give us greater scale. Because you can’t just hire one more engineer with the next managed services client that we bring on board. We have to make sure we are constantly staying up on the things we have to keep pace with from a technology standpoint. We are leveraging more and more osmosis between team members, so we get more work capacity out of the existing resources we have. But we go about it in a way that is systematic. So that even when we do have to grow the team, we’re still doing it in a way that is smart. It’s practical.

In the end, for everything that we do, not only do we have to do it efficiently, not only do we have to be process-driven, it has to be repeatable, quality, and it has to be very customer-service oriented. Delighting our customers, being proactive, being consultative in our service delivery, that’s really how we can hope to differentiate ourselves.


SC: The skills needed in your role are diverse: adaptability, creativity, leadership, and a strategic/fiduciary mind. Many operations leaders have a background in engineering, finance, or the liberal arts. What was your path to the role you have today?

DB: Yes, my path wasn’t traditional. I’m not an engineer. My focus in college was on business and communications. Sure, I took several computer programming classes, but that was just because I thought it would be a nice added-value when I got into business. My goal was to go into marketing, but that’s not where I started. My first job out of college was with Rockwell International as a technical trainer. They thought I had enough technical acumen to handle it, and they liked how I presented myself. It wasn’t where I expected to start, but it ended up being a great stepping stone in my career.

Eventually, I moved into sales support and consulting roles. I finally got into the product management ranks and, from there, progressed into running a business unit and global sales ops. Since then, my career has spanned running my own company to leadership roles overseeing both product and service lines in public- and privately-held companies. It’s been a great run over the years, and I find I can leverage so much of what I’ve learned just about every day here at Mindsight.


Leadership And Communications Perspectives


SC:  With a mind for strategy, you are likely responsible for determining how to use the expertise within Mindsight effectively. What kind of team talent is needed as you build and evolve the operations teams from the perspective of a VP of Operations?

DB: Certainly, team members must have the necessary technical competencies to fill the unique roles we have on our Operations team. But we also need our team to be comprised of professionals who are thoughtful about the solutions we are delivering and consider the end-game outcome of the customer. We appreciate creativity and we look for our team members to bring that kind of thinking forward with the solutions we deliver. One of the most important qualities I look for is being customer-service driven. We serve our customers, and we need people that believe that to their core.


SC: Effective communication is vital to leadership. What is your philosophy on communication? Has it evolved or changed based on your experiences? 

vp of operationsDB: Well, I’m a little old school in this area but at some level, you have to roll with the times. I am a believer in live communication, in person or on the phone. So much gets lost or misinterpreted over email or messaging apps. I know the latter is convenient, but I can’t tell you how many times I’ve seen issues arise because of miscommunication due to misinterpretation of tone or because of message brevity. As such, I and those with whom I work have to be sensitive to the way we communicate in writing versus verbally. And while I have evolved to see the role collaboration tools play in creating efficiencies in business, I would rather deal with essential tasks in person.



SC: A big part of what a VP of Operations is supposed to do is help drive cross-functional support for the business. How do you help interlock teams from various internal departments?

DB: When I joined Mindsight, this was one of my main objectives. It started with communications. I essentially eliminated bureaucracies and compensation matters that inhibited cross-team collaboration. I also addressed perception issues that existed between teams. Sure, in some ways, I mandated how things were going to be done, but more importantly, once I explained and continued to reinforce the benefits of what we were trying to do, people got onboard with it. When the teams support each other, we do better, more efficient work, for our customers and ourselves. I think that once this was evidenced in workloads and shifting mindsets, the rest really relied on consistency and opportunity on my end, so we can continue to grow that collaborative attitude.


Changes And Challenges For Business


SC: There is a lot happening in the technology world: AI, cloud technology, blockchain, IoT. What market trends are the most critical today in your view?

DB: I think there are a few key things going on that are game changers for everyone. One thing’s for certain: everything is changing very quickly. I think the ubiquitous nature of things is profound. With cloud computing and cloud-based applications, you get access to infrastructure – and capabilities and information – from anywhere. You can engineer for greater availability and accommodate elasticity to deal with variability in demand. Also, storing and retaining data is important, but understanding how to monetize data is becoming a key competitive driver for companies. Providers of technology and services don’t have the luxury of just selling point solutions to businesses anymore. You must think about the interrelationship between what business your customers are in, what are their challenges, risks and imperatives, and how you can align in a way to add quantifiable value. 


SC: What is the biggest challenge our clients face right now, and how do we go about solving those problems?

DB: It’s funny you mention this, because I was just talking with Ed Kapelinski, our CEO, about this. My conclusion? Time. Money. Risk. In my experience, when I’ve gone in to have a conversation with a customer, it is most effective to try and understand – what are you working on? What are the primary focus items for the business? What are your real imperatives? Okay, great. That all sounds good. Then you have to ask, what do you feel are some of the biggest risks and challenges you face? And, more often than not, if you just summarize what you would net from those conversations, it would come down to what I just said. Time, money, and risk.

vp of operationsCompanies have objectives and they only have so much time and money to work with to get them done. The market is hypercompetitive and it changes rapidly. Keeping pace with change is challenging, to say the least. The risk comes from the potential for failure. What is the risk to the business if you fail to accomplish the key initiatives that support the goals or the company? This can be a devastating outcome for a business.

We want to help our customers address these challenges. I think it starts with asking questions around what those key initiatives are, what is the expected benefit to the business, and what is the risk to the business if any of these objectives aren’t met? Then we can talk about how we can add value to help mitigate those risks.


The Mindsight Difference


SC: What is something people don’t know about you?

vp of operationsDB: Now comes the embarrassing question. Well, I spend my spare time playing bass guitar. I certainly spend more time practicing than I do playing in front of people. It’s something I took up only a few years ago. I can’t read music, probably never will, and I am still learning a lot of basic stuff. But it’s really satisfying as a personal outlet, and I have had the opportunity to play a few live gigs so that’s all good. One day, when I retire, I want to be in a little band that plays all the small pubs somewhere near a beach.


SC: What keeps you excited at Mindsight? 

DB: The people and the challenges. When I look at our Operations, I believe we have an excellent team. We deal with problems all day long, but we do it together, as a team, and people really do help one another out. The management team has great energy and enthusiasm, which keeps things moving and growing. We have challenges all the time. We’re either dealing with issues or we’re learning something new. In both cases we have to figure things out, and the process of problem solving gives you a regular sense of accomplishment.

Contact us today to find out how you can benefit from the insights of Mindsight’s VP of Operations as you develop your own business strategy.

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About Mindsight

Mindsight, a Chicago IT services provider, is an extension of your team. Our culture is built on transparency and trust, and our team is made up of extraordinary people – the kinds of people you would hire. We have one of the largest expert-level engineering teams delivering the full spectrum of IT services and solutions, from cloud to infrastructure, collaboration to contact center. Our highly-certified engineers and process-oriented excellence have certainly been key to our success. But what really sets us apart is our straightforward and honest approach to every conversation, whether it is for an emerging business or global enterprise. Our customers rely on our thought leadership, responsiveness, and dedication to solving their toughest technology challenges.

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About The Author

Siobhan Climer, Science and Technology Writer for Mindsight, writes about technology trends in education, healthcare, and business. She previously taught STEM programs in elementary classrooms and museums, and writes extensively about cybersecurity, disaster recovery, cloud services, backups, data storage, network infrastructure, and the contact center. When she’s not writing tech, she’s writing fantasy, gardening, and exploring the world with her twin two-year old daughters. Find her on twitter @techtalksio.

Mindsight CEO And President, Ed Kapelinski Talks Technology, Business, And The Future

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