#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 differently
- How to use personalization, targeting, and timing to get replies (not unsubscribes)
- The right way to blend automation and human touch in your outbound strategy
It’s an inside look at how marketers and founders approach outbound messaging, across strategy, execution, and scale.
Timestamps
- (00:00) - — Intro and guest lineup
- (04:04) - — Why most cold emails fall flat
- (06:04) - — Common copy mistakes: too much “I,” not enough “you”
- (07:34) - — The automation vs. personalization debate
- (09:49) - — When *not* to send a cold email
- (12:04) - — What targeting gets wrong (and how to fix it)
- (14:04) - — Teardown #1: Robotics email with 0% replies
- (16:19) - — Subject line issues, tone, and CTA feedback
- (18:34) - — Teardown #2: CRM campaign with profanity
- (20:19) - — Why this email screams “marketing,” not “outbound”
- (24:50) - — Teardown #3: Direct debit email repurposed from a nurture
- (27:20) - — Why HTML-heavy emails kill deliverability
- (29:05) - — Teardown #4: Founder-led cold email from Breakout
- (31:20) - — What worked: relevance, format, and intent
- (33:50) - — Teardown #5: Cybersecurity email to bank execs
- (35:50) - — Final takeaways on relevance, timing, and strategy
Send guest pitches and ideas to hi@exitfive.com
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