There are a number of companies that have failed to make the digital transformation.
Jeppesen, a company all pilots are familiar with, had two CEOs in a row since 1993 through 2016 that failed to make the digital transformation.
Jeppesen owned 97% of the aviation paper charting market. In fact, they OWN the worldwide navigation database those paper charts are derived.
They spent over $1 billion from 1993 to present and have yet to make a significant contribution to the digital age. The entire Electronic Flight Bag (EFB) market was theirs to define and own, yet, they failed. Mismanagement of hiring the MBA/PMP types with zero aviation or engineering experience, allowing the outright jealous hatred of pilots by their employees, the view that they were too big to fail, etc., all contributed to their demise. Boeing owns them and has been picking apart the bones. Soon there won’t be a Jeppesen left.
I have to agree, I really miss the free Jeppesen Internet Flight Planner from AOPA, I thought it was the best I ever used.