You can't be a superior engineering contributor unless you are honest with everyone, from superiors to peers, to reports. The key is how you present information. I just proactively scheduled a 1-1 with a Sr VP three levels above me for later this month to cover an important topic.

This is what I want to tell them:

Our core customer facing application is shit. The contractors who wrote it cut tons of corners and the marketing people who designed did a horrible job, the UI emphasizes features customers don't care about, and makes it extremely difficult for customers to actually reach and use the revenue generating sections of the app. Not only is the marketing leadership is disfunctional, and worse, you (the Sr VP) have created a disfunctional development organization, that makes me wonder if you understand how to develop commercial applications.

This is what I will say:

The weaknesses in our core application are costing the company millions of dollars a month. We are struggling with making quick, effective decisions and shipping new versions to address the major problems because we have "too many cooks in the kitchen" in our team meetings and planning. I will give specific examples and relate them to specific examples from my long history shipping quality commercial apps on time. I will finish by saying the team is demotivated and underperforming, which makes you, the Sr VP, look bad, and plead that we need to solve this, for them and the company both.