Creating Sales Emails with AI & Personalization | GTM Crossroads Ep #2

GTM Crossroads Podcast Ep #02: Creating Sales Emails with AI & Personalization

In the second episode of GTM Crossroads, RevPartners CEO Brendan Tolleson sits down with OutboundSync Founder Harris Kenny, and Octave Co-founder and CEO Zach Vidibor to explore the importance of effective email copy, market insights, and the evolution of personalization in outbound marketing.

Check it out! 👇

5 Minute Rundown:

Navigating Outbound Sales at Scale

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Harris: “There’s a bigger issue when scaling outbound—teams wonder, ‘Where am I supposed to reply from?’ That’s a lot more complicated than it seems.”

Scaling outbound isn’t just adding more reps and hoping for the best. It’s about building workflows that don’t turn into chaos. Managing multiple inboxes, keeping CRMs clean, and avoiding reply confusion are key challenges.

Success comes from clarity, like making sure reps know where to work and how to keep it all aligned.

Write Hyper-Personalized Emails

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Zach: “You don’t want your prospect to feel like they need to solve a riddle to understand what you do. Make it simple, clear, and actionable.”

AI can pump out emails at scale, but if they’re vague or sound robotic, they’re toast. The real win is Using your own ICP data to craft emails that feel like they were written just for the reader.

Think less “Hey {First Name}” and more “Here’s exactly how we fix your problem.”

Relevance Beats Personalization Every Time

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Harris: “People don’t care if AI wrote the email; they care if it speaks to a real pain point they have. That’s what makes them respond.”

No one cares that you know their college mascot; they care if you understand their pain points. Relevance is king. Forget cheesy first-name tokens and focus on their challenges, their role, and what you can actually fix.

Don't be afraid to take bold guesses and lead with real value.

Master Cold Outreach

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Brendan: “Executives read emails on their phones. If your message doesn’t fit on a single screen, you’ve already lost.”

Cold emails shouldn’t feel like reading a novel. Keep it short, clear, and phone-friendly. Offer something valuable without immediately asking for a meeting.

Instead of stressing prospects with a calendar link, invite them to check out something low-pressure, like a Loom video.

Don’t Ignore Your Warm Leads

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Harris: “The CRM has to be the source of truth. Otherwise, you’re just spamming the wrong people and creating noise instead of value.”

New leads are cool, but your existing database is a goldmine if you use it right. Set up your CRM to track key signals, then use that data to send the right message at the right time.

But remember, messy CRMs lead to spammy outreach. Get the data clean, or risk alienating your warmest prospects.

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Write smarter. Sell faster. Grow bigger.

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