He should definitely start reaching out now, filling out recruiting questionnaires at schools of interest and following up with emails. Coaches know that XC courses vary widely so XC times are not as important as track times. High placements in larger meets (big invitationals, state series, and postseason) are good. He can update via email throughout the season and then also during track season.
Be sure to cast a wide net. Make sure schools pass the “broken leg” test and are also affordable since there isn’t much money available for XCTF scholarships.
Good luck!