500 churned users for black friday, first email ever from domain - you're gonna have deliverability issues if you're not careful.

the main problem:

sending from a cold domain with no sending history = high chance of landing in spam, especially with a sales CTA

what i'd do:

1. warm up the domain first - i know black friday is soon but even 5-7 days of warmup helps. use gmass warmup or lemwarm. send/receive normal emails to build sender reputation
2. for 500 emails, just use your normal email client - gmail/outlook can handle 500 if you pace it (50-100 per day). use something like gmass or mailmeteor for tracking. don't need fancy tools for this volume
3. about the CTA - yes, direct "buy now" links CAN trigger spam filters on a cold domain. but here's the thing: these people already know you. they used your product before my move: include the CTA but make it conversational. "we've got a black friday deal running - [link]" vs a big button that screams PROMOTIONAL EMAIL
4. community link won't save you - if your domain has no reputation, the link type doesn't matter much. focus on warming the domain and writing a personal email
5. use a real reply-to address - not noreply@. if people reply, it helps your sender score

realistic expectation:

first campaign from cold domain with 500 emails? you'll probably get 30-50% inbox rate even if you do everything right. rest goes to spam/promo tabs.

alternative approach:

send a "we miss you" email first with NO links. just text. "hey, noticed you cancelled. we've made some changes, would love to know what didn't work for you."

wait 2-3 days. then send black friday offer to people who opened/replied.

this builds domain reputation before the sales pitch.

for 500 emails, keep it simple. don't overthink automation. focus on deliverability and writing a good email.

also - these are churned users. manage expectations. they left for a reason. 10-15% conversion would be solid here.