#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
- (04:37) - — Why most cold emails fall flat
- (06:37) - — Common copy mistakes: too much “I,” not enough “you”
- (08:07) - — The automation vs. personalization debate
- (10:22) - — When *not* to send a cold email
- (12:37) - — What targeting gets wrong (and how to fix it)
- (14:37) - — Teardown #1: Robotics email with 0% replies
- (16:52) - — Subject line issues, tone, and CTA feedback
- (19:07) - — Teardown #2: CRM campaign with profanity
- (20:52) - — Why this email screams “marketing,” not “outbound”
- (24:53) - — Teardown #3: Direct debit email repurposed from a nurture
- (27:23) - — Why HTML-heavy emails kill deliverability
- (29:08) - — Teardown #4: Founder-led cold email from Breakout
- (31:23) - — What worked: relevance, format, and intent
- (33:53) - — Teardown #5: Cybersecurity email to bank execs
- (35:53) - — Final takeaways on relevance, timing, and strategy
Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Today’s episode is brought to you by Paramark.
It’s November. 2026 planning is already here. And the stuff you’re doing right now will decide how next year plays out.
But here’s the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel. And you can’t make smart budget calls if you’re just guessing what’s working, what’s not, and where to put your next dollar.
That’s where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They’ve figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.
And right now, they’re offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly.
In this 45-minute strategy session, they’ll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that’s rooted in data, not gut.
This is a heck of an offer. And it’s real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don’t miss out on this offer.
Grab your spot at paramark.com/brand-consult.
***
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
The Dave Gerhardt Show