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The Nathan Barry Show

074: Alyssa Dulin – Secrets of Email Deliverability

60 min episode · 2 min read
·
Alyssa Dulin

Episode

60 min

Read time

2 min

Topics

Career Growth, Productivity, Health & Wellness

AI-Generated Summary

Key Takeaways

  • Positive Engagement Signals: Inbox providers track opens, clicks, replies, safe sender additions, and spam folder removals to build sender reputation. Getting subscribers to reply to emails provides particularly strong positive signals that messages are transactional and valuable, helping algorithms favor primary inbox placement over promotions.
  • List Cleaning Strategy: Sending to unengaged subscribers who leave consecutive messages unread creates negative signals that suddenly tank reputation and trigger spam filtering. Clean lists proactively using engagement scores, reduce frequency to cold subscribers, or implement reengagement campaigns at three to six month intervals to maintain healthy sender reputation.
  • Open Rate Benchmarks Post-iOS: Apple Mail Privacy Protection automatically opens tracking pixels regardless of actual user engagement, inflating open rates across the industry. Aim for 40 percent or above open rates now versus 30 percent pre-iOS changes. Focus on conversions and replies rather than opens for accurate engagement measurement.
  • Custom Domain Considerations: Using verified sending domains or dedicated IPs removes ConvertKit's reputation boost, requiring minimum 10,000 messages monthly and consistent sending frequency to maintain independent reputation. Shared IPs provide buffer against mistakes, time off, or engagement drops through pooled reputation with other quality creators.
  • MOG Membership Advantage: ConvertKit belongs to M3AAWG, an exclusive anti-abuse organization requiring strict application processes and proven spam fighting. Membership provides direct relationships with Gmail, Microsoft, Yahoo postmasters and Spamhaus, enabling immediate issue resolution that individual creators cannot access independently.

What It Covers

Alyssa Dulin, ConvertKit's head of deliverability, explains how email reputation systems work, what impacts inbox placement, why list cleaning matters despite revenue loss, and how positive subscriber signals like replies boost deliverability performance.

Key Questions Answered

  • Positive Engagement Signals: Inbox providers track opens, clicks, replies, safe sender additions, and spam folder removals to build sender reputation. Getting subscribers to reply to emails provides particularly strong positive signals that messages are transactional and valuable, helping algorithms favor primary inbox placement over promotions.
  • List Cleaning Strategy: Sending to unengaged subscribers who leave consecutive messages unread creates negative signals that suddenly tank reputation and trigger spam filtering. Clean lists proactively using engagement scores, reduce frequency to cold subscribers, or implement reengagement campaigns at three to six month intervals to maintain healthy sender reputation.
  • Open Rate Benchmarks Post-iOS: Apple Mail Privacy Protection automatically opens tracking pixels regardless of actual user engagement, inflating open rates across the industry. Aim for 40 percent or above open rates now versus 30 percent pre-iOS changes. Focus on conversions and replies rather than opens for accurate engagement measurement.
  • Custom Domain Considerations: Using verified sending domains or dedicated IPs removes ConvertKit's reputation boost, requiring minimum 10,000 messages monthly and consistent sending frequency to maintain independent reputation. Shared IPs provide buffer against mistakes, time off, or engagement drops through pooled reputation with other quality creators.
  • MOG Membership Advantage: ConvertKit belongs to M3AAWG, an exclusive anti-abuse organization requiring strict application processes and proven spam fighting. Membership provides direct relationships with Gmail, Microsoft, Yahoo postmasters and Spamhaus, enabling immediate issue resolution that individual creators cannot access independently.

Notable Moment

Dulin reveals ConvertKit turns down millions or tens of millions in annual revenue by rejecting customers who send cold emails or low-quality content, prioritizing long-term deliverability reputation over short-term growth to protect all creators on the platform from reputation damage.

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Episode Transcript

You want to receive positive signals from your subscribers and reduce the amount of negative signals that you're receiving. So some positive signals are opening the message that you send, clicking, responding to your message. That's actually a really big one. So getting your subscribers to reply to your emails is really, really great, adding you to their safe senders list or address book. If your message did land in their spam folder, if they mark it as not spam or move it out of spam, that's a huge positive signal. So those are all the good things that you want to see from your subscribers. In this episode, I talked to Alyssa Doolin, who is the head of deliverability for ConvertKit. So if you've heard around that ConvertKit has amazing deliverability, which is absolutely true and, you know, you hear a lot of creators talking on Twitter about how when they switched to ConvertKit, their open rates went up, their engagement went up, and that's because of the hard work that Alissa does behind the scenes. So in this episode, we talk about what professional creators need to know about deliverability, how the industry actually works, the semi secret organizations that exist behind the scenes. And then we even dive into a really fun new project kind of behind the scenes of what actually announced today when we're recording it and will have been maybe out for a couple of weeks by the time this episode airs. Well, behind the scenes is the deliverability and compliance side of how this secret new project is working. So there's a ton of stuff. Elyssa is seriously the best in the industry. She leads the industry podcast on this and everything else. So if you ever wondered about deliverability, this is the episode for you. Elyssa, welcome to the show. Hey, thanks for having me. I was just on your podcast about deliverability, which is the key industry podcast about deliverability I hear. Our creators reference it all the time. And then what's the most fun is when, like the rest of the people in the industry reference it. I love the fact that you're out there sharing, like our values of teach everything, you know, and work in public when your podcast is listened to by, I think most of the competition, because you're the only one actually talking about these things. Everyone else is like no deliverability is this like, opaque world, you have to, you know, be a member of our secret organization to know about it. And you're like, look, here's how it actually works. Here's what's going on. So anyway, I'm thrilled that you're talking about this. Maybe let's start there. Why do you talk about it publicly so much compared to the rest of the industry that tends to keep things these things very quiet and secretive? Such a good question. Well, I mean, if you're listening to this podcast, there's a good chance you send …

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  • Membership provides direct relationships with Gmail, Microsoft, Yahoo postmasters and Spamhaus, enabling immediate issue resolution that individual creators cannot access independently.
  • Alyssa Dulin, ConvertKit's head of deliverability, explains how email reputation systems work, what impacts inbox placement, why list cleaning matters despite revenue loss, and how positive subscriber signals like replies boost deliverability performance.
  • ConvertKit belongs to M3AAWG, an exclusive anti-abuse organization requiring strict application processes and proven spam fighting. Membership provides direct relationships with Gmail, Microsoft, Yahoo postmasters and Spamhaus.

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