Future Fuzz - The Digital Marketing Podcast Ep. 106 - Poke the bear....carefully. How to nail your reply rates with Margaret & Jakub - Woodpecker
In this episode of Future Fuzz, Justin welcomes Margaret Sikora, CEO of Woodpecker, and Jakub, Customer Success Manager, for a deep dive into the rapidly evolving world of cold email outreach. Together, they unpack why infrastructure is now a critical factor in successful campaigns, how outdated practices like "spray and pray" are sabotaging sender reputations, and why personalization without true market-fit is a waste of effort - even in the AI age. They also critique outreach tactics, explore the “poke the bear” strategy, and share real-world examples of reply rates as high as 95%.
Takeaways
- Cold email infrastructure matters more than ever; diversify your domains and ESPs.
- Never send from your main domain - burning it could wreck your business reputation.
- AI can’t fix poor product-market fit; it will just “multiply by zero.”
- Subject lines work best when they’re short, casual, and human.
- Reply rates can soar with strong targeting and thoughtful strategy (even up to 95%).
- "Poking the bear" can be effective - but only if you can back it up.
- Don’t test campaigns too narrowly; large samples yield better data.
- Outreach is about value and relevance, not gimmicks or over-promising.
Chapters
00:00 Welcome to Future Fuzz
00:45 Meet Margaret and Jake from Woodpecker
01:42 Why Email Infrastructure is Critical in 2025
04:05 The Role of Backup Domains and Mailboxes
06:29 Tools for Planning Cold Outreach Infrastructure
07:22 Average Reply Rates & What Influences Them
08:23 AI is Not a Fix for Bad Fit
09:48 Casual, Value-Focused Subject Lines
10:06 Campaigns with 95% Reply Rates - How?
11:34 Why Spray-and-Pray Tactics Are Dying12:05 What is “Poking the Bear” in Sales?
13:09 Why Testing Strategy Beats Guesswork
14:22 Scaling Tests Without Losing Insight
16:13 Cold Email Techniques Rated Rapid-Fire
20:43 The ROI of Knowing Your Audience
23:38 Where to Connect with Margaret and Jake
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