If you’ve ever wondered whether cold email is worth your team’s time, this episode covers why it still works when done strategically. You’ll learn how to deliver value at every touchpoint, increase response rates without spamming, and avoid the follow-up traps that kill credibility.
It is not hard to see why cold email gets such a bad reputation. Most executives say they hate receiving them. The inbox is overcrowded, subject lines feel robotic, and messages often read like they were stitched together by a template.
When Sarah Shepard and I sat down for this conversation, we laughed at how many people roll their eyes the moment “cold email” comes up. The truth is, the channel is not the problem. It is the way people use it.
“The tactic isn’t the problem. It’s the strategy and how you use it and the value you deliver.”
Cold outreach can still open doors if:
When those three things are missing, your emails do not stand a chance.
Let’s be honest. Most campaigns fail because they are built for speed, not impact.
“Every time you use ‘just checking in’ without adding new value, you’re just training prospects to delete it faster.”
Executives are not annoyed by the idea of email. They are annoyed by lazy outreach.
Cold email is still one of the most cost-effective ways to start conversations. The difference between campaigns that convert and those that flop comes down to four things.
Deliver Value with Every Touch
Each message should bring something new to the table — an insight, a data point, a resource, or even a perspective tied to what your prospect is dealing with right now. If you cannot answer “what’s the takeaway for them?” then it is not ready to send.
Diversify Your Touchpoints
We often hear that it takes 12 to 15 touches to convert a lead. That does not mean 15 emails. Mix in:
When your outreach shows up in different ways, it feels less like spam and more like persistence with purpose.
Personalize With Intent
The best cold emails feel timely and specific. Use public signals like funding announcements, leadership changes, or new product launches to guide your timing. As Sarah said, the best messages make prospects feel like you are “reading their mind.”
Test Like a Buyer
This is one of my favorite exercises. Print out your last ten outreach emails. Then ask your team: “Would you reply if this came from a competitor?” If the answer is no, it is time to rewrite.
Q: How many times should I follow up before stopping?
A: Focus on value, not volume. If you are just repeating yourself, you are done. If you are adding new relevance, you can keep going.
Q: What counts as a touch besides email?
A: LinkedIn comments, direct mail, phone calls, or even a quick connection at an industry event. Variety keeps it fresh.
Q: Why do my emails keep going to spam?
A: Filters catch spammy keywords like “just checking in” or overused gimmicks. Keep it straightforward and professional.
Q: How can I personalize without being creepy?
A: Use public signals like funding rounds, product launches, or content they have shared. Stay away from personal details that cross the line.
Q: Is AI useful for cold email?
A: Yes, when it helps you scale personalization. AI should make customization faster, not turn your outreach into copy-paste templates.
This episode features Sarah Shepard, COO of StringCan Interactive, and me, Jay Feitlinger, CEO. Between us, we have built and refined hundreds of outreach campaigns for mid-market companies. We know what it looks like when cold email drives real pipeline growth, and what it looks like when it fails.
“If you cut right to it and deliver value, that is where I see some amazing results.”
Cold email is not dead. It is just often rushed. When you slow down, personalize with intent, and focus on delivering value at every touchpoint, cold outreach can become one of the most efficient revenue levers in your pipeline.
For the full breakdown and real-world stories, listen to the episode on Apple, Spotify, Amazon Music, or YouTube.
If you are ready to fix your revenue engine, connect with our team at StringCan Interactive.