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How to Start More Sales Conversations. With Bridget Gleason. And special guest, Ryan O’Donnell [Episode 592]

Bridget Gleason is VP of Sales for Logz.io and my regular partner on Front Line Fridays. We’re joined on this episode by Ryan O’Donnell, CEO of SellHack and Replyify.


  • SellHack is a prospect list-building tool with email address verification for salespeople who don’t want to manage their address lists. Replyify is a cold email automation system.
  • Ryan’s motivation for these companies was his desire as an entrepreneur to spend his sales time having sales conversations, not entering data to feed the pipeline.
  • Ryan is writing a post on the psychology behind sales emails. Some people talk about email, some write emails, and some run experiments to quantify email testing. Ryan tests for high response and high engagement.
  • The psychology of cold emailing is the right person at the right time with the right message. Are you writing very specific campaigns for very specific segments? Ryan treats segments differently and writes the emails accordingly.
  • Andy and Bridget see people talking about segmentation and personas, but not much practical execution. Bridget remarks about timing and segmentation challenges.
  • Ryan offers his thoughts on personalization at scale. How many email campaigns does your team have active? One or two is not enough. Apply the scientific method. Ryan has 80 different but similar campaigns running currently.
  • Don’t send a test to 5,000 addresses. Divide into subsets and vary the test messages. Bridget talks about the campaign Logz.io marketing runs, and the various campaigns the salespeople run, which are segmented.
  • Ryan’s email Call To Action is an invitation to talk on the phone next week to see if there’s a fit. Not for a demo call, but for a few questions. Ryan has two categories of cold email and five sequences based on segments.
  • Ryan explains some segments. Ryan encourages listeners to examine how they are approaching cold outbound emails and to challenge their assumptions. He suggests running different edgy test campaigns.
  • Ryan discusses ads, showing up, calling, and emailing. If your message is easily consumed and your CTA doesn’t require deliberation, an email shows the most respect for a prospect’s time. It is most efficient. Learn how to do it.
  • In testing, you might find one that yields a 60% response rate. Double down on that one! Ryan suggests writing drunk and editing sober! He describes his process of writing to a LinkedIn group of people like him.
  • Andy invites listeners to share their email templates, and the best and worst replies they’ve received to their campaigns. Send them to Andy@AndyPaul.com or leave an audio message on AndyPaul.com about your experiences.