alt Hacker NewsIf it's been around for a while, look at the last year's worth of projects and estimate the total delay caused by the specific piece of tech debt. Go through old Jira tickets etc. and figure out which ones were affected.
You don't need to be anywhere close to exact, it's just helpful to know whether it costs more like 5 hours a year or 5 weeks a year. Then you can prioritize tech debt along with other projects.
It takes guts to say “this 1 month feature would be done in a couple days by a competent competitor using modern technology and techniques”, and the legendary “I reimplemented it in <framework> over the weekend” is often not well received.
But - sometimes drastic measures and hurt feeling are needed to break out of a bad attractor. Just be sure you’re OK with leaving the company/org if your play does not succeed.
And know that as the OP describes, it’s a lot about politics. If you convince management that there is a problem, you have severely undermined your technical leadership. Game out how that could unfold! In a small company maybe you can be the new TL, but probably don’t try to unseat the founder/CTO. In a big company you are unlikely to overturn many layers above you of technical leadership.