This bank started out as a small bank in Sheboygan, WI, and one con is that it has kept some of its small town mentality as it has grown. Some employees are very resistant to change and see working at the bank for 10+ years as a badge of honor, rather than seeing that they have outdated and stale ideas, and that there is much improvement to be made (technologically being one major example). The growth of the HSA industry has made it seem like what has been built previously is what made them successful, which is not necessarily the case. From an IT perspective, it can be like pulling teeth to teach long time employees/managers outside of IT things that have long been industry standard in tech.
On another technology note, leadership is just starting to realize that they have fallen behind and have fairly understaffed development resources for a company run largely via software. They needed management consultants to come in and tell them they needed to start widescale digital transformation efforts, but the consultants also did not tell them how to do that. So, instead of hiring people with these skills or relying on newer employees with backgrounds in digital transformation, they decided to let long time employees who have not led digital transformation efforts lead such efforts. One such group is their product management group, which is led by some of the least digitally-saavy product managers you will find. Lastly, their parent company is even slower and farther behind technologically, which makes it even harder to effect good change with agility as the parent company continues to take more control.
