Cold Email: Lessons from Real Outbound Campaigns in 2025

#249 Cold Email | In this episode, Danielle is joined by four experts in B2B outbound: Zoe Hartsfield (Apollo), Will Allred, (Lavender), Maximus Greenwald (Warmly), and Alex Fine (Understory). Together, they dive into the good, bad, and “please don’t ever send this” of cold email strategy. Each guest brings firsthand insight from scaling outbound at fast-growing B2B companies and helping clients do the same.Danielle and the crew cover:The biggest reasons cold emails flop and what great ones do differentlyHow to use personalization, targeting, and timing to get replies (not unsubscribes)The right way to blend automation and human touch in your outbound strategyIt’s an inside look at how marketers and founders approach outbound messaging, across strategy, execution, and scale.Timestamps(00:00) - — Intro and guest lineup (02:30) - — Why most cold emails fall flat (04:30) - — Common copy mistakes: too much “I,” not enough “you” (06:00) - — The automation vs. personalization debate (08:15) - — When *not* to send a cold email (10:30) - — What targeting gets wrong (and how to fix it) (12:30) - — Teardown #1: Robotics email with 0% replies (14:45) - — Subject line issues, tone, and CTA feedback (17:00) - — Teardown #2: CRM campaign with profanity (18:45) - — Why this email screams “marketing,” not “outbound” (21:00) - — Teardown #3: Direct debit email repurposed from a nurture (23:30) - — Why HTML-heavy emails kill deliverability (25:15) - — Teardown #4: Founder-led cold email from Breakout (27:30) - — What worked: relevance, format, and intent (30:00) - — Teardown #5: Cybersecurity email to bank execs (32:00) - — Final takeaways on relevance, timing, and strategy 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