Worked with static typing for about a decade primarily with Java in the enterprise. However, I've also used Haskell and Scala which have advanced type systems. I moved to work with Clojure about 8 years ago, and I don't miss types. If I did, I would've gone back to a typed language a long time ago.
My experience is that dynamic typing is problematic in imperative/OO languages. One problem is that the data is mutable, and you pass things around by reference. Even if you knew the shape of the data originally, there's no way to tell whether it's been changed elsewhere via side effects. The other problem is that OO encourages proliferation of types in your code. Keeping track of that quickly gets out of hand.
What I find to be of highest importance is the ability to reason about parts of the application in isolation, and types don't provide much help in that regard. When you have shared mutable state, it becomes impossible to track it in your head as application size grows. Knowing the types of the data does not reduce the complexity of understanding how different parts of the application affect its overall state.
My experience is that immutability plays a far bigger role than types in addressing this problem. Immutability as the default makes it natural to structure applications using independent components. This indirectly helps with the problem of tracking types in large applications as well. You don't need to track types across your entire application, and you're able to do local reasoning within the scope of each component. Meanwhile, you make bigger components by composing smaller ones together, and you only need to know the types at the level of composition which is the public API for the components.
REPL driven development [1] also plays a big role in the workflow. Any code I write, I evaluate in the REPL straight from the editor. The REPL has the full application state, so I have access to things like database connections, queues, etc. I can even connect to the REPL in production. So, say I'm writing a function to get some data from the database, I'll write the code, and run it to see exactly the shape of the data that I have. Then I might write a function to transform it, and so on. At each step I know exactly what my data is and what my code is doing.
Where I typically care about having a formalism is at component boundaries. Spec provides a much better way to do that than types. The main reason being that it focuses on ensuring semantic correctness. For example, consider a sort function. The types can tell me that I passed in a collection of a particular type and I got a collection of the same type back. However, what I really want to know is that the collection contains the same elements, and that they're in order. This is difficult to express using most type systems out there, while trivial to do using Spec.
[1] http://blog.jayfields.com/2014/01/repl-driven-development.ht...