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 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:Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive. ***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