How to Upgrade Your Webinar and Email Strategy for 2026 with Jay Schwedelson (Founder, SubjectLine.com)

#372 | Dave sits down with Jay Schwedelson, founder of subjectline.com and Guru Media Hub, one of the sharpest tactical minds in email, webinars, and live content. Jay explains why so many B2B marketers get live content wrong from the very first step, and how small shifts in packaging can completely change who shows up and who doesn't. They dig into the psychology behind when people actually open and engage with email, why shorter almost always wins, and the habits that quietly keep you out of the spam folder. Jay also shares the specific email and send-day habits he swears by, a few of his go-to tricks for getting people to actually reply, and how he thinks about testing your way to what works for your own audience.

Timestamps

• (00:00) - – Why "webinar" might be costing you registrations
• (01:12) - – Meet Jay Schwedelson and the virtual event he built to 30,000 people
• (06:26) - – A simple trick to get more people to actually show up live
• (08:44) - – Why giving everything away on-demand might be a mistake
• (10:23) - – The case for live, human connection in an AI-saturated world
• (13:00) - – The send times most B2B marketers are sleeping on
• (15:18) - – How to package and name your content so people actually want it
• (22:02) - – The newsletter habit that makes people stick around
• (26:09) - – Small email tweaks that quietly boost open rates and deliverability

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Brought to you by:

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Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.

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