The downside to this will be the negotiated rate, and that is the upside for Stripe.... along with the lower risk hiring outcome they also receive.
When time is not on your side your negotiating ability is severely hampered.
There will always be an imperative for someone in a team to "hurry the paperwork" along faster than someone else because they need the financial security of a job etc etc. So unless the "team" is happy to delegate the entire negotiating process to one person with complete authority this situation will be unavoidable. And let's face it, not many people will blindly put their faith in someone else to negotiate every aspect of their next full time permanent position, including whether or not to accept it and give notice at their current employer.
Money isn't everything of course, but this is a sure-fire approach to limiting your income, thus don't think there will be many takers.
As someone else said in the comments here, the more practical alternative that actually does work is called consulting.
In advertising agencies it's not unheard of to hire creative teams (for example an art director + copywriter duo) who are used to working together. In fact where I work most hires and departures in the creative departament in the past few years were in teams of two or three people.
I've never seen this sort of collective bargaining work in action for the reasons I outlined originally.
Given that the Dunning-Kruger effect has two parts (incompetent people overestimate themselves AND competent people underestimate themselves) this looks like a plus: You get a chance to hire people which are competent but aren't confident in their own competence and wouldn't apply if not for the team.