Jon Shearer served as head of digital products at Dave Ramsey, creator of Financial Peace University and numerous other products designed to teach healthy personal financial practices and get out of debt. This was during Ramsey’s migration as a company from a content producer and radio show, to a digital-first brand that can meet people where they are and support them practically.  

Jon talks about the highs and lows of leading a digital transformation, and how great technology had immediate impact on the company’s reach and revenue. He also gives great advice for navigating the recurring struggle between tech and business.

Topics by time stamp:

1:06 — What is digital transformation? How to ensure that you don’t get in your own way, and kill the very idea that could be the new life of your business.  

6:25 — Jon’s journey at Ramsey: where they started and how they evolved.  

12:19 — Leadership, aka, how to scale your team under you, why leadership in tech is different from other areas, and how to help other leaders understand tech within the organization. 

22:48 — How to create a culture where technology and commercial sides of the company understand each other, and work really well together. 

40:09 — What Jon is focused on right now: Advising and mentoring in leadership “wherever people are present”.  

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