What if the biggest thing holding your business back wasn't marketing, pricing, or lead generation, but the fact that everything lived inside your head? In this episode, I sit down with Jordan Craig, a wedding photographer who joined Systems in Session after years of managing inquiries, contracts, invoices, reminders, and client communication manually. Together, we unpack what happened when he moved from a patchwork process of Gmail, reminders, QuickBooks, and memory-based workflows into a streamlined Dubsado system designed to support both his business and his life.

Jordan shares what surprised him most about the experience, how automation improved his client experience instead of making it feel robotic, and why he believes he'll gain back more than 180 hours every year because of the systems we built together.

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00:24 - Meet Jordan

01:32 - The Chaos Before Dubsado

03:38 - Five Minute Proposals

07:15 - Email Like You Mean It

13:39 - Centralized CRM Wins

17:14 - Offboarding Reviews Blogging

18:54 - Automation Balance

21:08 - Next Services To Automate

24:33 - Timing Inquiries And 60 Days

30:17 - Favorite Parts And GPTs

Mentioned in this Episode