Packaging is a very "wasteful" process because it does require adjustments and unfortunately the waste cannot be re-use for anything else.
As I mentioned in my comment, your workflow seems fine. It's normal to have to do a mockup, show the dieline and printed sheet to the people who will assemble the product, revise the dieline if necessary and then go to production. And even after all this, there's still waste and adjustments because the stock will react differently depending on environmental factors, the prints and little mistakes too. You don't really have a choice to do a mockup unless you're always using a template that has proven to be 100% efficient.
It's unclear to me what's your production workflow is though, eg. if everything is done in-house. If it's all done in-house, then speak with the people on the assembly lines and ask them what they find challenging.
Packaging isn't easy because you need to calculate the thickness of the stock, adjust your folds and cut line according to this, leave a little room for people or machines assembling the wrapping, etc. So it's a lot about anticipating what can be challenging for the people after you on the production line, knowing your stock, preventing paper "cracking", etc. And honestly, wrapping is not that easy.
There's certainly software or commercial dieline you can have created for this but this has a cost too and will be created for a specific purpose. If your boss is doing 50 different types of dielines, with different stocks, he better plan a budget for this! At this point, it's starting to be engineering work, not printing. Unfortunately, I don't know any software created specifically for this but I'm guessing something like autocad might be what's used for this (plus you need to actually learn how to use the software). But in general, it's not necessary to use a software once you know what you're doing. If your team and company never did any packaging themselves, there's a learning curve and there's a cost to gaining that experience. Once you'll get your perfect formula, you'll still do a mockup but you won't need to worry so much about the dieline itself, especially if you're always using the same kind of wrapping. If you want to get some precise dielines done for you, you can always contact a packaging company.
Digital machines can look like everything is easy and everything will magically fit, but as with any other machine there's a certain level of expertise necessary to use them and the maintenance is also a big part of the quality control.
Now, for your dieline, I can't see the real dieline but it looks like you're using a lot of 90 degrees angles and the diecut is "too fit". In this case, you're not leaving much room for adjustment and human mistakes. So it's possible it never looks like it fits perfectly on the box.
Here's an example of what -- I -- would do if I had to create a dieline for this kind of project:
- Instead of using 90 degrees angles on the flaps, I'd use something like 85-87 degrees. The reason is: You don't want the flaps to be perfectly equals with the corners of the box because they might end up not sticking on the edges perfectly and it's also way harder to assemble since it needs to be glued 100% perfectly! You'll use the flap below that one to cover the box; it's the same concept when you wrap gifts manually. You need to think of your flaps as layers. The flaps that will be covered by another flap don't need to be at a 90 degree angle since they'll be hidden anyway.
- Make sure to leave some room for the height of the paper vs the
height of the box. You can't make it 100% fit or you'll have some
issues and bad folds. Ideally, that part of the dieline should be at
least 1/8" to 1/4" shorter.
- Don't use a perfect 45 degree angle for the corners; you might end up with parts of the box looking uncovered in the corners. You can use a smaller
angle and increase the length of that flap. That will give you some room to position the wrapping with the box.
- If your paper is thick, you need to calculate the thickness of the paper and add this to your folds. That means a thick paper will
require you to increase slightly the height of some flaps.
- I don't see any "score" line on your dieline; that's the fold lines. It looks like these folds were done manually, maybe I'm wrong.
If you don't have these then it's even harder to get a precise final
result because all folds will be slightly different. If you can create folds with your machine, do it. If you cannot, then make sure to add the angles I mentioned above, they'll be even more necessary in that case. If your digital diecut machine doesn't do any fold line, then I'd say your boss purchased the wrong machine for that kind of project. Fold lines/score are important because they avoid ugly things like paper cracking and serve as guidelines too, they add precision (http://www.technifoldusa.com/bindery-success-blog/bid/39886/Why-is-Creasing-or-Scoring-Paper-Important)
- What you can do to make your boss happy is to work on the angles of
your dieline, leave some room for mistake so it requires less
adjustment (it's also faster to assemble, eg. lowers the
production cost as well) and stick to the formula that works well for your type of packaging. Not only you need to plan how the dieline will look like once cut but also how every single flap and fold will be glued together on the assembly line and in what order this will be done.
- You mentioned a packaging company; if you do work with a packaging
company doing the production process for you then maybe you could ask
them some tips.
- You might need to practice and find your formula on some non-client
projects. It will leave you more freedom to experiment and you can do it with extra waste from other projects too.
- You can also ask the manufacturer or salesman who sold the digital
diecut machine to your boss. They will be very happy to prepare a new
quote for extra equipment or software.
Something like this (not a precise example):
My experience is in commercial packaging on offset and digital printing. I'm actually the person who used to create and fix designers' dielines, and the tricks above are meant to accelerate the production process and lower its costs too.