Credit to Remianen on the TEW Forums and the anon who posted this as a screenshot. Slightly edited for TEW 2020.

Question: How do you get someone over in small fed?

Answer:

Actually, the same applies as a larger fed. Remember that grades are relative to a promotion size so a 50 rated segment in a local promotion is FIRE!  At those sizes, you don't want your workers getting over quickly because they'll move beyond your budget.  Unless you're like me and use your most over workers multiple times per show (and you really should), that could make them cost-prohibitive.

At local (Insignificant/Tiny) and small, my most expensive workers are often the people who can affect the show in more than one way. In past games, I typically splurged on a highly rated Road Agent for this reason. If you've been to any micro-indy shows at all IRL, you can easily get an idea of how things should probably work. The typical formula I've seen is:

Open angle with authority figure (usually owner/booker)
Match between trainees (often a tag)
Midcard vs Midcard
Promo by worker(s) in the advertised main event
Upper mid vs upper mid match
Promo by other worker(s) in advertised main event
Main event match, sometimes ending in a schmozz featuring everyone else who worked on the show

As you can see, everybody worked at least twice in the show. That's a value proposition. That also happens to be how it's done in real life, many times. Think of John Cena with the US Open Challenge. He'd come out and cut a promo (angle), lay down a challenge (angle), someone answers the challenge (angle), then they'd have the match. That's four uses from THE top guy, on a written contract. Vanity booking does the same thing (think of HHH and Steph during The Authority bit - 20min opening angle then lors of multiple smaller angles during the show).

If you have trouble getting your main eventers over but your undercard has no issues, try pitting your main eventers against your best undercard workers but don't use the "Open Match" note. The goal is to make the main eventer seem a lot better (you probably don't want this as your main event). Or, open your show with a squash with a main eventer and an undercard worker. The undercarder worker can be made up later but you're trying to boost your headliners so it's all good.