AI is making everyone ‘better’ at sales prospecting — and that's exactly the problem.
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.
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.
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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 the ‘Magic Insight’ framework for high-value outreach.
What most people get wrong about AI prospecting is that they focus entirely on company-level personalization — funding rounds, product updates, company news — rather than connecting with the actual person. To really stand out, you need what we call a “Magic Insight.” That insight is a personal, often funny connection that shows you understand the individual you're reaching out to.
To test this approach, we experimented with sales prospecting platform Scout AI on the podcast. The platform scanned my online presence and almost immediately identified a quirky detail that I'd mentioned in previous interviews: my love of ketchup. It then suggested this detail as an email opener.
This kind of specific, personal connection creates an entirely different level of engagement and shows that you’ve gone beyond standard company research.
Caveat: The key to making this framework work is understanding when to use it. Not everyone has a robust enough online presence for AI to find these personal insights. So, if you can't find enough information about someone, stick to company-level personalization. You're better off with a solid company-focused message than forcing a personal connection that feels thin.
3. Turn your data into a competitive advantage.
The key differentiator in AI prospecting success isn’t the technology itself — it’s the quality and uniqueness of your data. So while everyone else is relying on the same public information, successful companies stand out by using their proprietary data in new and creative ways.
For example, when we started using AI to analyze customer interactions at HubSpot, our first-touch email conversion rate increased by 94%. Why? Because AI is better at matching problems to solutions than traditional segmentation — but only when it has rich, proprietary data to work with.
This requires going beyond basic CRM data and tracking meaningful customer interactions across all touchpoints. In other words:
- What do you know about your prospects that no one else does?
- How do prospects engage with your product documentation?
- What features do they use in your free tier?
- How do they interact with your social media content?
These digital breadcrumbs can inform more meaningful, contextual outreach that goes beyond what standard AI tools can generate.
Ready to get started? Start small by connecting your CRM to Zapier. Use OpenAI to analyze prospect behavior and craft personalized messages, then automatically feed these back to your sales team through your CRM.
4. Understand your customers’ language.
Veteran Advertiser Claude Hopkins got it right decades ago when he said, "Marketing is just talking the language of your customers."
In other words, don't use jargon. Don't use corporate speak. Just talk to your customers like they're friends. And now, AI makes this easier than ever to scale.
At HubSpot, we've been building what we call a "customer language repository" — a collection of successful sales calls, support tickets, and product reviews that we analyze with AI to help us understand exactly how our customers describe their challenges and needs in their own words.
But the real game-changer comes from turning this analysis into action. We then use AI to categorize these conversations into key themes and patterns, creating a foundation for all our prospecting communications.
So when a sales rep reaches out to a new prospect, they're not just using generic AI templates. They're speaking the same language as our most successful customer conversations. (In my opinion, it's like having a souped-up Grammarly that corrects your writing while also aligning it with how your best customers actually talk.)
Tool stack tip: start with transcription tools like Otter.ai, then use ChatGPT or Claude AI to analyze patterns. For scale, you can build a custom GPT trained on your customer language data to review all outgoing communications.
To learn more about AI prospecting strategies, check out the full episode of Marketing Against the Grain below:
This blog series is in partnership with Marketing Against the Grain, the video podcast. It digs deeper into ideas shared by marketing leaders Kipp Bodnar (HubSpot’s CMO) and Kieran Flanagan (SVP, Marketing at HubSpot) as they unpack growth strategies and learn from standout founders and peers.