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

#329 | Dave is joined by Jay Schwedelson, Founder of SubjectLine.com and GURU Media Hub, to break down why most webinars and email programs underperform and what to do instead. They talk about how packaging drives performance, why the word “webinar” kills registrations, and how small tweaks like renaming your session, shortening it to 22 minutes, or adding an “attend to receive” hook can dramatically increase show rates. Jay also shares tactical email plays, from using white space and tighter subject lines to increasing reply rates and improving inbox placement.Timestamps(00:00) - Why packaging matters more than the content (01:43) - Jay’s virtual event business and the GURU acquisition (04:29) - Why you should stop calling it a “webinar” (06:24) - The “attend to receive” tactic to boost show rates (08:58) - Why on-demand is hurting your engagement (13:07) - Why Fridays and Sundays outperform for B2B email + webinars (16:40) - How to choose webinar topics based on your goal (17:07) - Why 22-minute webinars and shorter podcasts win (26:16) - The white space + no preview text email hack (34:28) - The “reply with GUIDE” tactic to boost engagement (36:14) - Final takeaways and wrap-up Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Webflow - A website platform built for the agentic web, helping modern marketing teams build fully custom sites—no developer needed—that perform in AI search. Learn more at webflow.com/for/exitfive.Markup AI - A content quality platform that scans your content against brand voice, preferred terms, messaging standards, and AI-search readiness before it goes live, right inside Google Docs. Learn more at markup.ai.Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Learn how to deploy agents on your marketing team at Agents in the Mix. Learn more at optimizely.com/exitfive. Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive, or check out the MCP server by clicking this link.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more