The popularity of Microservices and the other answers here suggests that your boss is correct in "the typical case". Your argument seems to be that the typical case is not absolute and that exception software engineering can deliver extremely high-quality software in a single large code delivery.
If I were you boss I would smile and tell you that while I hope for exceptional software I plan on the occasional worst case of average software. If your boss wants you to spend more time breaking down your delivery into smaller incremental features to reduce risk then, well, they are the boss.
Your boss appears to be indicating that they want to see smaller releases or feature flags. You are then saying "Actually, no, as I am delivering superior engineering through A, B and C". This is probably not a great career move, as your boss is saying they think things are actually too risky, they want you to push out smaller releases, and you are making a general argument that they may be wrong in some cases.
The correct way to think about this scenario is not pondered "who has the correct view of software engineering?". The correct way to think about this is the cost/benefits to yourself. Consider that you take the advice or ignore it:
(A) you get to push out a big code drop, or
(B) you do as your boss says and break things up into smaller code drops
Then some possible outcomes at the next release:
- there is a bug that has a negative business outcome, which includes superficial reputation damage as well as actual financial damage.
- the code is great. no significant defects. no negative business outcomes.
There is likely to be no win for you if you ignore your boss:
{A,1}
a big code drop and a negative business outcome. You ignored your boss and thing went bad. You should get fired.
{B,1}
you did smaller changes. A subtle bug led to a really bad outcome. Your boss knows you did your best and took their advice. You don't get fired.
{B,2}
you did as your boss asked. Nothing went bad. Win-Win.
{A,2}
a big code drop and no negative business outcomes. Yet you have actually ignored your boss on matters of risk which is their responsibility. This is a Win-Lose. You are a gambler who now needs to win every time as the first time you slip up your boss is going to pound you.
My advice is that when it comes to risk assessments then it is the boss's view, where they may know of political risks they cannot share with you, that is paramount.
When I have been the boss in such cases where there I flag up risks and the developer pushes back it is usually because of developer fatigue:
Dev: "This code is ready to ship."
Me: "Hum, this looks risky, because of ..."
Dev: "Nah, I have had enough of this code and I want to ship it. Things will be okay because of X, Y, and maybe Z."
Me: "Let me tell you a story, I did this feature and things went bad because of ... but I didn't get fired as my boss and my team stood by me."
Dev: "Er. Well, if you really want me to do more work to {write tests, simply the code, add a feature toggle, break it up into smaller releases, change the error handling to fail-fast, use a library not my customer algorithm, do rigorous performance profiling ...} (delete as appropriate) then I can.
Me: "Thanks. I really appreciate it."
In general "I don't want to do more work" isn't really a great basis to argue with your boss ;-)