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: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