Episode 27: How AI Killed Cold Prospecting

Camela Thompson, Head of Marketing at RevOps Co-op, sat down with Liv Porter from Cloud Adoption Solutions to unpack a hot-button topic: how artificial intelligence (AI) is reshaping outbound sales and prospecting. With a background rooted in user adoption theories and a passion for RevOps, Liv shares her insights into the rise and fall of traditional outbound strategies and how AI is both a challenge and an opportunity in the modern sales landscape.

If you’ve ever wondered why cold outreach seems harder than ever or how AI tools are influencing email deliverability rates, this episode is for you! Camela and Liv tackle how teams can adapt to stand out in an increasingly noisy marketplace.

The Evolution of Cold Outbound: From Effective to Ineffective

A decade ago, outbound prospecting was a reliable playbook. Marketing teams would focus on SEO and inbound strategies, and sales teams could leverage personalized cold emails to generate leads.

“Back in 2016 or 2017, I remember being impressed by how personalized cold emails felt,” Liv reflects. Fast forward to today, and reply rates have plummeted. “Reply rates that were once 15% are now closer to 1-2%, and inboxes are noisier than ever.”

So, what changed? Two major factors:

1. AI-Fueled Spam Detection: Email platforms like Google and Outlook now use AI to filter out what they deem irrelevant or spammy.
2. Over-saturation: With more software companies and more tools enabling high-volume outreach, buyers are inundated with irrelevant messages.

Why Are Companies Still Relying on Automation?

Despite declining results, many companies continue to rely on automated outreach tools. Liv attributes this to a mix of outdated advice, poor change management, and a natural tendency to cling to what worked in the past.

“A lot of advice out there is from 2022, but tactics that worked then won’t work now.” — Liv Porter

Camela adds, “Scaling what doesn’t work just burns through your database. Poor outreach not only damages your brand but also risks your email domain reputation.”

The Points of Failure: Technology, Process, and People

Liv identifies three core reasons for poor outbound results:

1. Over-Reliance on AI Tools: AI-generated emails are often based on outdated templates that lack originality. Both human readers and spam filters can detect these patterns.
2. Lack of Persona Understanding: SDRs often blast emails without understanding pain points or tailoring messages to the target audience.
3. Bad Follow-Up Habits: Post-event or post-conversation follow-ups often lack personalization, leaving prospects feeling ignored.

Where Do We Go From Here?

So, what’s next for cold outbound in a world where AI filters and buyer fatigue dominate? Liv sees three paths:

1. High-Volume Play: If your product is transactional and broadly applicable, high-volume outreach can still work—but only with proper domain rotation and high-quality content.
2. Personalization at Scale: For more complex sales, teams must prioritize creative and meaningful messaging that resonates with the buyer.
3. Relationship Building: The most promising path involves going back to basics—networking, building trust, and using events to connect with prospects.

Camela concludes, “There’s no silver bullet. It’s about nailing the fundamentals and recognizing that good relationships take time.”

Final Thoughts: Adapt or Perish

The era of spray-and-pray emails is over. AI has changed the outbound game for good, and companies must adapt to survive. Whether through better content, smarter technology use, or a return to relationship-driven sales, the key is to strike the right balance between technology and human connection.

PS - Liv will be on stage at RevOpsAF 2025 speaking on this topic if you want to see her live in action.