Independent and freelance makeup artists, hairstylists and high-end nail techs make up a large and quickly growing segment of the beauty industry. They have no time and no business and marketing experience to re-engage and retain customers. GlossGenius offers a digital personal assistant that helps these independent beauty professionals earn more income through deeper client engagement and marketing automation. The personal assistant--named "Gloss"-- proactively gets clients back in the door and scheduling appointments. Gloss can accept bookings, automatically prepare personalized appointment reminders, prepare beautiful follow-up emails, and intelligently use client history data to proactively prepare personalized client re-engagement messages containing content, maintenance care suggestions and re-booking nudges. Like its customers that are hyper active on text messaging, Gloss lives on text messaging and operates through an approval-based text-message workflow.