I'm sure you realize that as Rookies you are not eligible for the Chairman's Award, but are preparing one to help with the Rookie All-Star Award. And it is a good idea anyway, as described in the Manual (copied below).
There are many examples of Chairman essays online that would help you. Check the CD-Media section. Our essay and posters we used (from 2007, which are a little dated now) is at
http://moe365.org/chairmans_path.php
6.4.2 First-Year (Rookie) and NASA Grant Teams:
Because the Chairman’s Award recognizes sustained excellence and impact, not just a one (1) year team effort, it is not possible for a first year (rookie) team to receive this honor. FIRST does, however, invite and encourage rookies to develop a Chairman’s Award submission which may be evaluated by the judges determining the winner of the Rookie All-Star Award. This submission will document where the team started its FIRST journey and will also provide background for documenting the results of the team’s efforts – it will be a great way to start the team’s efforts to win the Chairman’s Award.
Rookie Teams: If you prepare a Regional Chairman’s Award submission, print a copy to give the Judges when they visit you at your Pit Station. Judges will not be viewing them online.
Teams receiving NASA Grants must provide a copy of this submission as part of the grant.