#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
- (03:38) - — Why most cold emails fall flat
- (05:38) - — Common copy mistakes: too much “I,” not enough “you”
- (07:08) - — The automation vs. personalization debate
- (09:23) - — When *not* to send a cold email
- (11:38) - — What targeting gets wrong (and how to fix it)
- (13:38) - — Teardown #1: Robotics email with 0% replies
- (15:53) - — Subject line issues, tone, and CTA feedback
- (18:08) - — Teardown #2: CRM campaign with profanity
- (19:53) - — Why this email screams “marketing,” not “outbound”
- (23:19) - — Teardown #3: Direct debit email repurposed from a nurture
- (25:49) - — Why HTML-heavy emails kill deliverability
- (27:34) - — Teardown #4: Founder-led cold email from Breakout
- (29:49) - — What worked: relevance, format, and intent
- (32:19) - — Teardown #5: Cybersecurity email to bank execs
- (34:19) - — Final takeaways on relevance, timing, and strategy
Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership
***
Today's episode is brought to you by Knak.
Email (in my humble opinion) is the still the greatest marketing channel of all-time.
It’s the only way you can truly “own” your audience.
But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.
That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.
- Frustrated by clunky email builders? You need Knak.
- Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
- Big team making it hard to collaborate and get approvals? Definitely Knak.
And the best part? Everything takes a fraction of the time.
See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.
***
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 Exit Five CMO Podcast (Hosted by Dave Gerhardt)