The Transaction | AI-Powered Cold Calling & SaaS Sales Strategy with Justin Michael & Charles Needham

AI-Powered Cold Calling & SaaS Sales Strategy with Justin Michael & Charles Needham - Ep 60

July 22, 2025 / 59:51/S2 E60

What if cold calling isn’t dead—but everything we know about it is?

From dissecting permission-based openers to dunking on dated tactics, Justin and Charles make a bold case for why the phone isn’t dead—it’s just misused.

Justin Michael, aka the John Wick of executive coaching, is the Founder of the Justin Michael Method and co-author of The Cold Call Algo. Along with being Justin’s Co-Author on Cold Call Algo, Charles Needham is the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools.

Critical Takeaways

Encouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships.
The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement.
Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes.
Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation.

Chapters

00:00 Intro

01:09 Introducing Justin Michael and Charles Needham

02:55 Discussing B2B Sales Strategies and Cold Calling

03:37 Justin's Sales Stories and Experiences

08:07 Charles on Modern Sales Challenges

13:22 The Role of AI in Sales

17:10 Cold Calling Techniques and Best Practices

30:29 Debating Cold Call Openers

32:53 Unified Theory of Cold Calling

39:03 Mastering Tonality and Rhythm

56:26 The Future of Cold Calling

Epic Quotes

“Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham
“Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham
“ People buy emotionally, they justify with logic.” - Justin Michael

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