Robert Wheeler

CTO at Stealth AI Startup

Can you please provide a little introduction about yourself

Rob is a Chief Technology Officer with over 25 years of experience in the technology industry. He has a proven track record of success in leading and managing technology teams as a very hands-on player/coach, developing and implementing innovative solutions, and driving business growth.

Rob is currently acting as a Fractional CTO for small, well-funded startups where he is responsible for the company's overall technology strategy and development direction. He has a deep understanding of the latest technologies and trends and uses this knowledge to develop solutions that meet the needs of the business.

Rob is also a strong leader and communicator. He is able to motivate and inspire his team to achieve their goals, and he is able to clearly articulate the company's technology strategy to stakeholders.
Rob is a graduate of the University of Maryland and an 8-year Service Medal
Veteran of the USAF.

What path have you taken to your current position? 

I had a progressive path starting out as a developer, working my way into more senior-level roles, and then ultimately into management roles.  

I started out working as a developer and in some cases, a computer operator working on a local area network and then ultimately working my way into development, which I enjoyed and thought was a better spot for me to be in.

I've had some good milestones, mostly around startups and exits and I was pretty proud of that, so I tried to stay within the startup world ever since. 

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?

I never really thought of it as being a vision; it just kind of happened.  I wanted to help lead and run startups, and I did what I had to do to get there.  

I can't say it was a vision, but it certainly turned into one.

Have you had a role model or mentor that has helped you on your journey?

Yes, one of my early mentors was a boss of mine at a very, very large company that really gave me advice and put me on a really good track to become a better leader. 

He was a very successful advertising executive, and to this day, I still speak to him about my journey. Robert William Schrijver.

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

There's a lot of fruitful conversations going around about this topic.  Many CTOs believe that they should be focused on strategy and only strategy and not getting themselves involved in the architecture in code and I believe that is incorrect.  Technology leaders are gonna have to be more focused on the engineering part of it considering what's going on with AI and where it's going to take us.

I do believe it's gonna make things significantly easier on the Development side.  The emphasis for tech leaders will be transformation. They will have to have the ability to deal with these transformative systems, like AI and ML. LLMs are going to become more dominant, and more practical, and the content will balloon. 

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

Good question.  The ability to adapt is the ability to change your mind based on evidence of the way things are changing now. This is going to be a critical ability that tech leaders are going to need to have. Steve Jobs was known for this.

Decisions are going to be made based on data more and more data is going to be available with the advent of AI and machine learning. #DATA will rule.

Leaders are going to have to be knowledgeable of the technology and comfortable navigating that technology. Not only do they have to understand the latest and greatest, but they have to be able to leverage that innovative culture and transform business models.   It's a continuous learning environment for technology leaders. There are many other things that leaders will need to engage in. 

Is there anything in particular that you would still like to achieve in your career or what is the next step on your journey?

I've had some success with startups, so my next achievement requires that I engage with another startup to build some AI tech that I've been toying with over the past few months. i want to scale that and see that technology come to fruition. 

What role do you see emerging technologies (e.g., AI, machine learning, blockchain) playing in your industry, and how are you preparing for them?

Emerging technologies are going to have a profound effect on most industries.  I suspect the evolution of personalized shopping and the way that retail and big box stores operate will dramatically transform. It will be unrecognizable to the current human in 10 years.

You will see analytics start to take over, where everything is done based on data. Blockchain technology will start to transform things like supply chains, pure energy, trading payments, and crypto, and will become a bigger and bigger piece of our economy. 

"As a technologist, it's important that we all stay up-to-date with the latest and greatest trends and tools that we are using."

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

I use the entrepreneurial operating system and I focus on rocks, which are essentially project-related activities that need to be accomplished.  so that makes communication easier because it's already informative on the leadership side because it was previously set. 

So I think this type of communication and collaboration will only need to continue to improve to be candid technology at all levels from junior developers to CTOs need to understand what the goal of the business is what the strategy of the business and that technology needs to focus on those, levels.  Establishing that culture in the beginning is crucial.

How do you ensure that you and your team stay updated with the latest technology trends and industry best practices?

As a technologist, it's important that we all stay up-to-date with the latest and greatest trends and tools that we are using, or could potentially be used in whatever world or industry we are building in. 

You have to share your knowledge,  you must set up protocols for your team to communicate with tech sessions for example, or develop an internal knowledge base,  have a mentorship program, cross-functional working groups, and things of that nature will allow you to stay abreast of what's going on and active engagement with your ecosystem is critical to stay abreast and keeping up-to-date with the latest.

Team demos are fun, to be honest. when you do that with a dev team, it's truly a set of conversations that are quite enjoyable. 

A big thank you to Robert Wheeler from Stealth AI Startup 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.