#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
(03:41) - — Why most cold emails fall flat
(05:41) - — Common copy mistakes: too much “I,” not enough “you”
(07:11) - — The automation vs. personalization debate
(09:26) - — When *not* to send a cold email
(11:41) - — What targeting gets wrong (and how to fix it)
(13:41) - — Teardown #1: Robotics email with 0% replies
(15:56) - — Subject line issues, tone, and CTA feedback
(18:11) - — Teardown #2: CRM campaign with profanity
(19:56) - — 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

***

This episode is brought to you by Webflow.

If you're a B2B marketer right now, you’re probably being asked to do more with less - less budget, fewer resources, tighter timelines. And you’re expected to somehow grow pipeline anyway.

That’s why more teams are switching to Webflow.

Webflow is the website experience platform that helps you consolidate your stack, reduce program spend, and move faster. Instead of juggling a dozen tools and waiting on devs, Webflow gives marketing and design teams the power to build, launch, and optimize sites all in one place.

No-code flexibility. Dev-level control. Built-in A/B testing, SEO, localization, and AI tools. It’s everything you need to turn your website into your highest-performing channel.

It’s everything you need to turn your website into your most efficient, highest-performing channel.

Check it out at webflow.com/exitfive.

Cold Email: Lessons from Real Outbound Campaigns in 2025

The Dave Gerhardt Show (from Exit Five)