Wednesday, December 2, 2020
Home CIO Spotlight CIO Spotlight: Dean Crutchfield, EVP & Chief Information Officer at CDK Global

CIO Spotlight: Dean Crutchfield, EVP & Chief Information Officer at CDK Global

Walk us through your CIO path. How did you decide to pursue a career in technology, and how did you progress to your current organization?

Early in my university experience, I was a business school student unsure of where to focus my major: accounting, business operations, MIS, etc. I took my first programming course and I knew immediately that MIS would be my major. I have always been drawn to practical, tangible improvements and I could see how programming and other technologies could be applied to improve and scale a business. I was also drawn to working with people in leadership roles early in my university experience and post-university.  I was always one of “those people” volunteering for leadership roles in associations like the Society of Information Managers, PC User Groups, and eventually as a volunteer television producer on an educational technology program that I started on PBS. 

I’ve been blessed to work in companies and in roles that worked closely with geologists, geophysicists, electrical, mechanical, and software engineers, and that has shaped my preference to work with technology-oriented companies and people.

As I progressed in my career, these early leadership experiences helped me understand the importance of an organization’s mission, values, servant leadership – attributes essential to someone leading volunteers.  I enjoy technology, and especially the people in technology roles who operate, secure, and innovate every day to help companies meet their goals and objectives. I’ve been blessed to work in companies and in roles that worked closely with geologists, geophysicists, electrical, mechanical, and software engineers, and that has shaped my preference to work with technology-oriented companies and people. Given the strategic importance of digital, the mission-critical requirement of a secure, reliable, and cost-effective digital ecosystem inside all organizations today, the opportunities associated with working with technologists to make a difference in our organizations has never been more exciting.  

Tell us about your company.  Speak to the industry, size of the company, and the services provided to your customers.

CDK Global is a SaaS provider to 30K transportation dealers globally which means we work with global transportation manufacturers as well as their dealers. Our annual revenue is $2B and we have over 1M subscribers to our platforms.   

What are your top 3 – 5 (ongoing) main priorities as a CIO in your organization?

We’ve been focused on enabling transformation and modernization of our software installation and customer service processes and technologies. We’ve also been modernizing and transforming our core software products moving to modern API, Microservice and Cloud architectures. Finally, data and insights are a huge priority, we are increasing the velocity of offering insights to the transportation industry to help all partners in the ecosystem operate their business more intelligently.    

How do you decompress from your role as a technology executive?  What do you do for fun?

I’m an avid cyclist, hiker and skier – both water and snow skiing. I enjoy being outdoors and especially now with being more locked down and working remotely, I appreciate the opportunity to get out and exercise more than ever.

Can you list your top 1 – 3 books that you would recommend for a technology leader to have on their bookshelf/Kindle?

  1. The Innovator’s Dilemma by Clayton Christensen
  2. Emotional Intelligence by Daniel Coleman
  3. FYI: For Your Improvement by Michael Lombardo 

The Innovator Dilemma and Emotional Intelligence are enduring leadership reads. FYI: For Your Improvement is a great coaching reference guide for developing others.

Can you share a specific quote that is a source of inspiration for you as a leader?

Envy is the enemy of joy and learning.

You can always find something wrong if you approach people with judgment or jealousy.  Just remember you can always learn something too and stay joyful.

Please share a recommendation or testimonial on the benefit that you see as a member of this CIO Professional Network.

I love to learn and it’s so critical to all CIOs and technologists to be vigilant learners. The CIO Professional Network enables me to learn from others in the network while providing additional learning benefits like the Executive Book Summaries, Research Briefs, and LeadershipX.  I’m inspired by the willingness of the community to contribute to the learning of others and am enjoying contributing as well. Being a member of the CIO Professional Network has challenged me in a positive way to be a contributor as well as a more effective learner.

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