The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

Cold Email: Lessons from Real Outbound Campaigns in 2025


Listen Later

#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 [email protected]
    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 Zuddl.

    We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.


    Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

    Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

    On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.


    If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

    Head over to zuddl.com/exitfive to learn more. 


    ...more
    View all episodesView all episodes
    Download on the App Store

    The Exit Five CMO Podcast (Hosted by Dave Gerhardt)By Dave Gerhardt

    • 4.7
    • 4.7
    • 4.7
    • 4.7
    • 4.7

    4.7

    38 ratings


    More shows like The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

    View all
    The Digital Marketing Podcast by Ciaran Rogers, Daniel Rowles and Louise Crossley

    The Digital Marketing Podcast

    114 Listeners

    The Smart Passive Income Online Business and Blogging Podcast by Pat Flynn

    The Smart Passive Income Online Business and Blogging Podcast

    3,449 Listeners

    Social Media Marketing Podcast by Michael Stelzner, Social Media Examiner

    Social Media Marketing Podcast

    1,447 Listeners

    The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship by Omer Khan

    The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship

    181 Listeners

    The Official SaaStr Podcast: SaaS | Founders | Investors by SaaStr

    The Official SaaStr Podcast: SaaS | Founders | Investors

    175 Listeners

    Marketing School - Digital Marketing and Online Marketing Tips by Eric Siu and Neil Patel

    Marketing School - Digital Marketing and Online Marketing Tips

    1,256 Listeners

    Noah Kagan Presents by Noah Kagan

    Noah Kagan Presents

    906 Listeners

    The CMO Podcast by vYve & Jim Stengel

    The CMO Podcast

    348 Listeners

    Creator Science by Jay Clouse

    Creator Science

    457 Listeners

    GTM Live by Passetto

    GTM Live

    201 Listeners

    The Marketing Millennials by Daniel Murray

    The Marketing Millennials

    147 Listeners

    Marketing Made Simple by Powered by StoryBrand

    Marketing Made Simple

    292 Listeners

    Marketing Against The Grain by Hubspot Media

    Marketing Against The Grain

    352 Listeners

    Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold by GURU Media Hub

    Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold

    713 Listeners

    AI Explored by Michael Stelzner, Social Media Examiner—AI marketing

    AI Explored

    78 Listeners