Inyssius, all of the three Insider pieces I've worked on started with Chris Youngs coming to me with a specific assignment he needs to fill, along the general lines of "an article about X as part of the Y series, ### words total with ## words of flavor hook."
I then come up with some ideas about how to approach that: for example, these are the suggestions I had for the piece that became Warden Essentials:
The idea I like best for the flavor hook is the Forest Moon, which is a silver crescent symbol that woodsfolk hang up in a tree when they need help. The origin of the symbol is that the sight of a warden's curved polearm blade (referencing the class archetype the char op guys call the "reacher") rising out of the treetops like a waxing crescent moon was a sign of hope. Because of the fearsome reputation of the wardens, hanging up the crescent can often serve as a scarecrow to keep trouble away. Putting glyphs on the crescent can serve to alert forest defenders of specific types of peril, like bandits or an incursion of kruthiks. I like this because it references the warden but can provide a hook for any party members, and any warden can make it part of their own story - it's not something you have to build in at character creation, although we can offer some reach weapon-focused mechanics.
Other ideas I had were:
- Mossbacks are an order of wardens known for encouraging forest mosses and lichens to grow on their armor and vestments. These growths remain on them even when they are in guardian form. There could be a mechanical effect of the moss (e.g. treating it like a magic item or feat in addition to a mossback paragon path) but mostly I thought of it as a visual cue that'd make for a striking illustration.
- The Lost College was a campus of the War College (referenced in other articles in this series) that was destroyed and its ruin overgrown by wilderness. The College still has students, however. Some wardens claim to be taught directly by the ghosts of the former instructors, while certain fey and woodland types have also set up shop in the ruins to pass on the lineage of the wisdom imparted to them by the ancient spirits. Those wardens trained by the Lost College have certain distinctive abilities (game mechanics here), but are regarded with suspicion or scorn by affiliates of other War Colleges.
That's not the same as a pitch that I initiated, but it might give you some idea of the level of detail I've used in communicating with Chris about projects he initiated. This was my first Insider assignment; in later ones I think I've been even briefer in my thumbnail sketches.
However, I think the more useful advice is "how do I get to be in the position of having Chris come to me with assignments?"
For me, this came about because I responded to an ad for a staff designer at the
Wizards job page. I didn't get hired for the full-time position, but as the second step of the application I was asked to submit a design test that involved writing powers, monsters, etc. Based on that opportunity to show my chops, James Wyatt offered me an assignment doing a section of Martial Power II (and also gave me individual feedback on the design test that substantially improved said chops).
Design jobs don't get posted all that often, but you should certainly apply when they do - even if relocating to Renton is unlikely, my experience suggests you could parlay it into freelance work from wherever you are.
In the meantime, build your chops by doing as much RPG writing and networking as you can! James cited the fact that I'd done other published game writing as another reason he offered me the opportunity, and things like the Goodman Games open call for rituals or the Paizo Superstar contest are, I suspect, substantially easier ways "in" than cold querying for Insider. I can't emphasize enough that getting published is based much more on effort than merit; my first RPG writing credits were self-published, which is increasingly easy to do, and later 3PP assignments came along because of personal contacts I'd made while recruiting for campaigns, running games at conventions, seeking people out online, etc. Again, having some self-published writing you can point to when you make contact with people is very helpful.