Automated Gumroad Video Drip

I run a subscription product on Gumroad and need the entire email-automation flow built so my members start receiving fresh video content—three messages a week—without me lifting a finger.

Here’s the goal: every Monday, Wednesday, and Friday a new email lands in a subscriber’s inbox with the week’s video, audio or form already embedded in the body of the email. The videos are not on YouTube, Vimeo, or any mainstream host; they sit on a private location I’ll share with you once we start. The embed must play smoothly across the major email clients (desktop and mobile) and respect any size or codec constraints those clients impose.

What I need from you
• A working automation that triggers automatically for every new or existing Gumroad subscriber on the correct days, time and in the correct order.
• An email template that pulls in my thumbnail, description, and the fully embedded video.
• A simple way for me to swap in next week’s video batch without breaking anything.
• Clear, step-by-step documentation (screenshots or loom video fine) so I can maintain or tweak the workflow later.

Preferred tools are Gumroad’s native email system plus Zapier, Mailchimp, ConvertKit, or another platform if it handles embedded playback better—open to your recommendation, as long as it keeps costs low and the user experience high.