There exist both tech-minded church leaders and faith-driven technologists. Yet there are few opportunities for these two groups to interact. 1 Chronicles 12:32 mentions a group of people (tribe) known as the sons of of Issachar, noting that they “understood the signs of the times and knew the best course for Israel to take.” We are now in and have been for some time, the Digital Age. With this has come an entirely new way to communicate with others, solve complex problems, and advance the Gospel. What may be needed in response to those “signs of the times” is a synergy between the tech-minded church leaders and faith-driven technologists. These two groups uniquely understand the signs of the times, and understand the best course to take. There are many barriers preventing this. What are they and how can we overcome them?