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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Jonathan Ozovek

helps you in your leadership.



Jonno White

7 Questions with Jonathan Ozovek

Name: Jonathan X. Ozovek

Current title: Chief Operating Officer

Current organisation: Commonwealth of Virginia - Virginia Information Technologies Agency

Jonathan Xavier Ozovek is the first Chief Operating Officer (COO) of the Virginia Information Technologies Agency (VITA) for the Commonwealth of Virginia. As VITA’s COO, he leads enterprise IT services, service delivery, operations, supply chain management, customer success, investment governance, project management, and finance.
Prior to coming to the commonwealth, Jonathan has extensive experience in the private sector across the healthcare, consulting, financial services, and technology verticals and across the globe. This experience has been across nimble technology startup companies to industry leaders such as PricewaterhouseCoopers (PwC), Johnson and Johnson, Becton Dickinson, Siemens Healthcare, and Citibank. He specializes as a turnaround and transformation executive with a proprietary methodology that delivers measurable outcomes rapidly. This methodology has delivered quantifiable top and bottom line improvements of over $200 million within a range of one to two years.
In addition, Jonathan has a penchant for research, development, and innovation with a specialty in artificial intelligence, predictive analytics, and machine learning. He has designed and developed systems ranging from a predictive commodity trading system, a medical device research and development Enterprise Program Management (EPM) system, and a cutting-edge last mile logistics platform and SaaS solution..

7 Questions with Jonathan Ozovek


1. What have you found most challenging as a CEO or executive of a large enterprise?

As one progresses in their career and their responsibilities increase, the scope and focus of what they lead broadens exponentially. When leading small teams or a department, I was able to develop a personal rapport with my team and I could understand their motivators at a micro level and adjust accordingly to achieve the objective.
As I have risen in my career, this has become less feasible as the number of people as well as communication channels multiplies. At the highest level, you have to see the entire chessboard, understand the direct and indirect interdependencies, and take actions which have a high probability of influencing certain factors which ultimately allow the enterprise to achieve macro level strategic objectives.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I have followed a less than traditional career path across multiple disciplines and industry verticals; however, the common thread was an obsession to learn as much as I could about industry factors and also the functions within organizations to rapidly increase my underlying skill set. Over time, this has resulted in a great body of knowledge, adaptability, and resiliency which serves me well in transformation and turnaround scenarios as well as accelerating technological and process innovation forward!
In my career, I came from the absolute bottom to become one of the youngest Senior Vice Presidents on Wall Street, worked as a private equity executive to transform troubled enterprises, led technology and operations for a publicly traded SaaS company, to now being the first Chief Operating Officer for VITA in the Commonwealth of Virginia, I feel extremely blessed to be in my position and use my pulpit to give opportunities to the next generation of leaders.

3. How do you structure your work days from waking up to going to sleep?

This is a great question and I have five children and a beautiful wife, so work/life balance is crucial. Our last daughter was just born this past December 23rd. My family is the most significant blessing in my life and serves as my rock.
Upon waking up in the morning around 0400, I take care of my kids by setting up breakfast, setting up coffee for my wife, and then physically train for about 1-2 hours before the work day starts. I have found that physical exertion helps me go into work with an endorphin rush as well as a clearer mind. It serves as an advantage.
As an executive, you cannot predict how many hours you may have to work and it is situational. There are critical initiatives, programs, and projects that I will monitor on a consistent basis. For operations, I heavily utilize data analytics with leading/lagging indicators to determine progress and where some underlying issues may arise so I assume a proactive posture. Additionally, I make myself accessible to my staff and will have a variety of conversations throughout the day to help wherever I can and also to help them if needed. I strongly believe in servant leadership, so sacrificing time to be accessible and communicate with my teams is the least I can do for what they are sacrificing for me and the organization.
A very important thing with my family now is that we sit down for dinner every night, so depending on the work situation, I will take a break and have dinner with my wife and kids. This serves as the end of the work day or a brief respite if there are critical items that are being tracked down. After dinner, I will help get the younger kids ready for bed and put them to sleep while my wife puts the baby to sleep. Then, my wife and I try to spend time at the end of the day to bond and discuss what is on our minds before bed. This part is important as it nourishes the relationship.

4. What's the most recent significant leadership lesson you've learned?

The most important lesson that I have learned and incorporated into my approach is to go into the game with no ego. No person is an island. In order to achieve critical and significant strategic organizational outcomes, you NEED your people. How you develop a motivated and engaged organization all starts with for you as a leader, trust that you have their backs, and trust that you are bringing the organization to a much better place. If you do not spend time building that trust, you ultimately will be unsuccessful.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Early in my career, I read The Goal by Eliyahu Goldratt and it changed the way I looked at organizational issues and optimization. This book covers the theory of constraints and incorporates the Socratic method as a way of diving deeper into problems. I incorporate these techniques into my leadership methodology to fully understand the constraints and set up my teams for success. In addition, it helps me guide my teams to develop solutions, which increases organizational sustainability and momentum.

6. How do you build leadership capacity in a large enterprise?

First, you have to be the example and a model of the behaviors you want to see in others and implement a mentorship culture. Second, you have to establish an environment where people are recognized, rewarded, and promoted based on their outcomes and capabilities. If you have top talent and they do not see an environment where they can accelerate their careers, they likely will accelerate their career elsewhere. Many organizations operate where leaders are protective of their spot, hence do not make a serious effort to develop highly talented people at the lower levels. Effective leadership capacity is developed by incorporating mentoring and opportunities within the DNA of your organization. True leaders develop other leaders.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

A meaningful example so far has been the technology transformation in Virginia that I’m currently leading. I am very proud to be here and working with the great team I have at VITA. Here, the transformation from the previous to the future state was extremely challenging. VITA was transitioning to a multi supplier integration model (MSI) from a single monolithic supplier who was uncooperative which is the worst situation you can walk into for that particular scenario. To date, we made significant progress in less than a year and a half during my tenure as the first COO of VITA, defying nearly all expectations from internal and external stakeholders. The situation I came into was unstable, chaotic, and in need of stabilization and clear strategic direction.
My answers to the previous questions resonate when I think about the transformation currently underway in Virginia. I came in here, to Virginia, and understood the issues within the current state and envisioned a future state which would make us by far the best state in the country as it pertains to technology. I worked extensively on building trust with our staff as well as the governmental agencies who are our customers and got them to “buy in” to the future state so we were all moving in the same direction. Trust was built through speaking truth to power, letting the staff know I have their back, implementing a culture based on data, accountability, results, and elevating talented folks into leadership positions as an example to the organization. Furthermore, I espoused a culture whereby relationships with our suppliers were mutually beneficial and focused on “win-win” opportunities to hasten the progress in certain areas. Execution has been and will be everything at the end of the day.
Against all odds, everything has come together and the strategy is executing extremely well, although there is still work to do. I am extremely thankful to be working with top notch staff under my organization as well as mutually beneficial relationships with top tier technology suppliers.

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