ROBERT KOVSKY

Chief Information Technology Officer at BWG Strategy

Can you please provide a little introduction about yourself
I am currently based in central New Jersey and am the CTO of BWG Strategy and OTR Global (recent acquisition). I have always been an avid technologist, adding a CD-ROM drive to my old 386 at age 7, and an entrepreneur having started my first business in PC Repair and Pop-up Blocking at age 12.
 
I like to think of myself lately as a change catalyst, bridging the great Tech<>Business divides, and helping businesses better leverage technology for growth. 
 
What path have you taken to your current position?

I have consistently straddled business and IT throughout my career. I started with a brief stint in pure Tech building networks and on-prem infrastructure mostly for SMBs rolling out their first ERPs in the early 2000s. Taking an interest in the ERP side I moved into the implementation side managing Dev and Project teams for VAR and eventually falling in love with the transformational power of CRM. 

I moved out of Consulting after a near decade, and into the Satellite Communications Business (SES) where I established CRM and Commercial Applications as a strategic pillar for business growth and created a global department. Here I was given the opportunity through the High Potential \ Leadership Development Program to earn an MBA and truly add Business credibility to my established technical background. 

Finally, the entrepreneurial bug caught me and I joined my current company, a primary research producer, as CTO following its founder handing over to Private Equity. The PE firm brought me in as part of the professional management for the “startup” looking to double in size and digitize its customer experience. 

Has it always been your vision to reach the position you’re at? Was your current role part of your vision to become a tech leader?

Yes, though I would have NEVER guessed the industry. As I continue to progress in my career, I continue to enjoy taking on bigger and bigger challenges.

While we are a medium-sized business at best, being in the C-suite has taught me a lot of valuable lessons with a wide range of topics.

Have you had a role model or mentor that has helped you on your journey? (If you feel comfortable, please share their name and how they helped you)

I’ve had dozens of great examples I often reference throughout my career. Some on what to do and how to think about problems, and plenty of examples of how not to think about things, or handle situations which are equally relevant. One that sticks out was an IT Director at a pharma I was consulting for.

I told him I was hoping to be in his seat one day. He looked at me and pointed and said “No you don’t, you want to be over there” pointing out the building next door on the campus housing the Sr. executives. We had a long talk I will never forget about aiming high, etc. 

Another, Stefan Okhuijzen, took me under his wings at SES and regularly opened up about a “way of thinking” that I have blended into my own style. We took many decisions together and ran many projects together, and I am ever grateful.

How do you see the role of the technology leader evolving over the next 5 years?

The biggest difference I see is the savvy of the new generations joining the workforce. The “consumerization of corporate IT”, BYOD, SAAS, Remote, etc. generation that is digital native working alongside a generation that is less means bridging solutions and change management at a new dimension. Just wait for the workforce to be part GenX-Z and part AI… 

CIO Guest interview 1

What skills do you think leaders of the future will need in order to thrive?

Simply put, it’s the Human skills. Much of the operational work will be automated-driven. It’s human communication, motivation, change management, etc. along with a DEEP understanding of how technology can impact, vs. specifics of how it works which will be abstracted. 

Is there anything in particular that you would still like to achieve in your career or what is the next step on your journey?
At my core, I am a change catalyst, and I continue to take on bigger and bigger initiatives. Once this one is over the hump and settled, there will be a new bigger one to come. One day the right idea will strike and I would like to build from the ground up. 
 
What advice would you give to aspiring technology leaders who are just starting their careers?

Get comfortable saying “I don’t know” and especially “Can you please help me understand”. Your peers and managers are generally eager to help. It’s human nature. Importantly, limit it to once if possible and take notes! As much as I love teaching, It’s less exciting showing for the 8th time. Come with ideas, come having tried something, but find the right balance. Don’t come on the due date asking for help, but don’t come after 10 seconds of thought either. 

The ones who deliver are the ones who get the high workloads, and eventually the recognition. Go the extra mile. Go in person and get face time at the right cadence for your situation, but be visible (for the right reasons), and when you go to make your next move, leadership will be more favorable to those who they know, human nature.

"Come with ideas, come having tried something, but find the right balance."

How do you measure and communicate the value and impact of technology initiatives to other business leaders and stakeholders?

WIIFM. While it is changing fast, historically talking about the technology itself has put leaders outside of technology to sleep. "What’s In It For Me" is the question that most non-technical people ask from the start, so start with that explanation.

While touching on why an idea is a Novel or a specific portion of the breakthrough can help to give credibility, nobody cares how cool it is, how long it took (sunk costs), etc. They want to know why they need it in their lives what risk it mitigates, what cost savings the solution will yield, what opportunities it opens, etc. 

Can you share a book that has the most profound impact on shaping your professional journey and approach as a leader?
 
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The 7 Habits of Highly Effective People by Stephen R. Covey
 
One of the most inspiring and impactful books ever written, The 7 Habits of Highly Effective People has captivated listeners for nearly three decades. It has transformed the lives of presidents and CEOs, educators and parents - millions of people of all ages and occupations.
 
Now, this 30th-anniversary edition of the timeless classic commemorates the wisdom of the 7 Habits with modern additions from Sean Covey.
 

 

A big thank you to Robert Kovsky from BWG Strategy for sharing his journey to date.

If you would like to gain more perspective from Tech Leaders and CIOs you can read some of our other interviews here

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The CIO Circle Editor
Post by The CIO Circle Editor
May 20, 2025