The Sales Prospecting Paradox: How to Stand Out When AI Makes Everyone Sound Good

Download Now: Free Sales Prospecting Guide + Templates
Kipp Bodnar and Kieran Flanagan
Kipp Bodnar and Kieran Flanagan

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AI is making everyone ‘better’ at sales prospecting — and that's exactly the problem.

marketing against the grain explores prospecting

I get laughably bad sales prospecting emails every day. I mean really bad. But that’s swiftly changing, with AI making it increasingly easy for just about anyone to craft polished, personalized messages at scale. But therein lies the paradox.

AI is turning sales prospecting into a commodity. Soon, your prospects' inboxes will be flooded with AI-generated, B-grade outreach that all sounds remarkably similar: Good enough not to be ignored but rarely good enough to stand out.

Download Now: Free Sales Prospecting Guide + Templates

As a result, traditional prospecting strategies lose their impact. So, what steps can you take to rise above the noise and connect with contacts in ways that actually break through?

In a recent Marketing Against the Grain episode, Kieran and I discuss four high-impact strategies we've discovered through our work and tests at HubSpot. Let’s dive in. 

1. Build brand recognition beyond the inbox.

When anyone can reach your prospect’s inbox with AI-generated perfection, you need to figure out how to be visible elsewhere. This means showing up where your prospects spend their time outside of email — and making those interactions count. 

For example, look at how Bland AI went beyond digital outreach, turning physical billboards — something many people see in their daily lives — into an interactive, AI-powered sales pitch.

You also need to think beyond basic company updates or product announcements for messaging. Your YouTube content should showcase real thought leadership. Your LinkedIn should spark genuine industry conversations. The goal isn't just to broadcast but also to build recognition and trust before prospecting ever begins. 

This way, when that AI-powered email finally does arrive, the prospect thinks, "Oh yeah, I know these folks." And that recognition — earned through consistent presence both online and off — is something no AI tool can replicate.

2. Use...

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