230: Cold Emailing in 2025: Mastering Deliverability & Outbound Success

ARRtist on AIR - Meaningful conversations with Software & AI leaders

With Margaret Sikora - CEO at Woodpecker

Is your cold outreach landing in spam? The rules of email deliverability are changing fast, and if you’re not adapting, your outbound strategy is doomed to fail. In this episode, Margaret Sikora, CEO of Woodpecker, shares her expert insights on email deliverability, domain reputation, and outbound best practices for 2025.

WHAT YOU WILL LEARN IN THIS EPISODE 🔹 The 3 Pillars of Email Deliverability Success Why technical setup (SPF, DKIM, DMARC) is critical for inbox placement How email copy quality and engagement signals impact deliverability The importance of list hygiene & validation to avoid spam traps 🔹 Why "Spray and Pray" is Dead – Micro-ICPs Are the Future Why highly targeted outreach wins over mass email blasts How AI & automation tools help personalize at scale The role of U-to-I ratio (talking about "you" more than "I") in boosting replies 🔹 How to Scale Email Outreach Without Burning Your Domain The risks of using your main company domain for outbound How to set up secondary domains & scalable mailboxes for high-volume sending Why email warm-up is crucial to maintain a good sender reputation 🔹 Why Cold Emailing is Still One of the Most Cost-Effective GTM Strategies How outbound stacks up against paid ads and LinkedIn outreach When and how to integrate multi-channel cadences (email + LinkedIn + calling) The legal side of outbound in Europe – What you really need to know about GDPR 🔹 Practical Quick Wins to Improve Your Cold Emailing TODAY The one thing you should change every two months to avoid spam filters The must-have tools for email validation, domain setup, and copywriting Why iterating your messaging frequently is key to long-term success

** Key Takeaways:** Deliverability is everything – if your email doesn’t land in the inbox, it doesn’t exist Targeting is more important than volume – micro-ICPs outperform mass mailing Domain strategy matters – never send outbound from your main business domain AI & automation help, but there’s no silver bullet – human strategy is still key Cold emailing is evolving, not dying – but only for those who stay ahead of the curve

Our Guest: Margaret Sikora https://www.linkedin.com/in/margaretsikora/

Our Host: Julius Göllner https://www.linkedin.com/in/julius-goellner/

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**Unser Werbepartner: ** Float

Restaurant Tipp:

Młoda Polska bistro & piano https://mlodapolskabistro.pl/ Wrocław, Poland

Recommendations & Sources:

Woodpecker Website: www.woodpecker.co ARRtist Circus: www.arrtist-circus.com