Cold Email Outreach with Jeremy & Jack

#404 - Transforming Silent Rejections into Profits


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About this episode (#404):

In this episode, Jeremy and Jack dive into a smarter way to structure follow-up emails in cold outreach. Instead of repeating the same call-to-action (CTA) or simply lowering commitment levels, they introduce a sales-letter-inspired approach using upsells and downsells to increase engagement and conversions over time.

Key Topics Discussed:

  • Why sending the same CTA in follow-ups is a missed opportunity
  • Introducing a follow-up "ladder" with escalating and descending offers
  • The psychology behind "foot in the door" vs. "door in the face" techniques
  • Using varied offers (video, guest post, webinar, trial) to maintain attention and add value
  • Why the third ask might get a "yes" even if the first two didn't
  • How to keep leads in your universe (e.g. newsletter, YouTube) even if they're not ready to buy
  • The importance of investing thought into offers, not just copy, during outreach planning

This episode is a goldmine for anyone running outbound campaigns and tired of stale follow-ups. Rethink your offers, make your asks more strategic, and turn "no response" into lasting brand engagement.

About the hosts:

Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/

Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

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Cold Email Outreach with Jeremy & JackBy Jeremy Chatelaine and Jack Reamer

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