AI Challenges in Sales Prospecting

Every B2B sales tool today: "We're powered by AI!" Ughh. Are you? I talk to dozens of founders every month. Most have been burned by buying "AI sales tech" That was just a basic GPT wrapper. With good marketing. 🙈 ❌ THE PROBLEM TODAY: So many "AI" sales vendors today demo well. But their actually product? It's not really AI. It's an API call. To ChatGPT... The red flags you should look for: 🚩 Template based responses 🚩 Minimal error checking 🚩 Basic API calls We've tested so many of these tools ourselves. And guess what? They failed to verify basic company data. They misunderstood qualification tasks. They sent emails with wrong context. That's because they're treating "AI" like... A fancy version of mail merge. SO... What should you look for? 2️⃣ What AI Sales infrastructure SHOULD look like Your AI sales stack needs these core components: Multi-Source Verification: - Cross-reference data across 3+ sources - Source tracking for every data point - Real-time accuracy validation - Automated fact-checking Context Management: - Industry-specific knowledge bases - Historical interaction memory - Company relationship graphs NOW... Here's where I'd focus your AI sales agents first 👇 Start with research heavy tasks. Things like: Lead Research: - Identifying expansion opportunities  - Analyzing technographic data - Mapping org structures - Finding trigger events Prospect Qualification: - Technology stack analysis - Company size verification - Recent company changes - Budget signals BEFORE YOU BUY... Look at THESE metrics 📈 "What are your accuracy rates?" Ask them for: - Research verification percentage - Data freshness metrics - Error correction stats - Learning curve data "What are your performance metrics?" - Error reduction over time - Processing speed at scale - Consistency across tasks - Adaptation to feedback THEN... Here's how I'd do a roll out 1️⃣ MONTH ONE - Audit manual research tasks - Document qualification criteria - Map current research workflow - Identify verification sources 2️⃣ MONTH TWO - Test AI on small lead segment - Measure accuracy vs humans - Document error patterns - Refine verification process 3️⃣ MONTH THREE - Scale successful processes - Build feedback loops - Train team on collaboration - Measure productivity gains -- P.S. Always ask AI vendors: "Show me your error rate metrics" If they can't, you know what you're dealing with. Have more questions? Hit me up in the comments or DM me!

If your reps didn’t know how to prospect before, AI just helps them do it faster. And worse. Sales teams are racing to slap AI onto their prospecting workflows. Custom GPTs, intent data engines, AI-personality profilers…it’s starting to feel like MORE tech is the answer to FEWER responses. But here’s the thing: We all know by now that AI isn’t the magic bullet. Bad inputs = bad outputs. The folks I see using AI properly are doing the following: 1. Using AI to prep smarter, not spam harder. AI tools that analyze 10-Ks, earnings calls, and LinkedIn posts? Gold…if reps know what to look for. Example: Instead of “Congrats on your funding!” (the most overused opener ever), a rep could say: “Noticed your Series B is aimed at scaling product. We’ve helped [competitor] cut onboarding time by 40% - thought it might be relevant.” 2. Custom GPTs built around their data. Some teams are building internal GPTs trained on their closed-won deals, past proposals, and customer calls. The result? AI that mirrors their own voice, knows what messaging actually works, and avoids the generic stuff ChatGPT spits out. 3. AI-Powered research, human-powered messaging. AI should handle the grunt work, like digging through data, summarizing insights. But the message? That still needs a human touch. The best reps blend AI-driven intel with personality. Think less “perfectly optimized email” and more “insightful, relevant, and human.” What’s NOT Working? - Mass personalization at scale. (Spoiler: It’s not really personalized.) - Relying on AI to write the whole email. (Prospects can smell a ChatGPT draft a mile away.) - Using AI without strategy. (More data isn’t better if reps don’t know what to do with it.) The reality is that AI is making bad prospecting louder. The winners? They’re using AI to do what it does best, which is research, prep, and pattern recognition. But the messaging? That’s still where the real game is played. Prospects don’t want to talk to robots. They want value. They want Insight. They want a reason to respond. Use AI as your sidekick, not your crutch. Because at the end of the day, the best sales weapon is still the same: A rep who actually gives a damn.

The Liar’s Dividend is the biggest challenge to sellers right now, and nobody is talking about it. ⛔ Maybe a little hyperbolic… but let me make my case. The Liar’s Dividend describes the benefits accrued to bad actors when misinformation makes us distrust all information, even the good stuff. Why is this a problem for sellers? AI tools make it easy for people to create outreach at scale (think of all the people on LinkedIn hawking their new “AI-powered” apps for sales). So yes, it could help create new emails or phone scripts. But it’s also going to: 1️⃣ Further clog your prospects’ inboxes and social media feeds. 2️⃣  Make them distrust all outreach even more. That second one is the doozy. If someone isn’t sure about what to trust, they don’t trust anything. If someone has to think “Did a 🤖 write this?” about emails or LinkedIn messages, they’ll just stop paying attention. They don’t have the bandwidth for it. This means that if you are trying to start new relationships, i.e. cold call, cold email, cold InMail, it’s going to get even harder. Because people will just ignore all of it. That doesn’t mean that these communication channels won’t be useful, just that they won’t be as useful for starting relationships. There’s going to be a continuing arms race as we get more tools for outreach and more defenses against outreach. What can you do to make your digital engagement more effective in the meantime: Go out and meet people. In the offline world. Go to events, have coffee, shake hands and meet in person. That way, tools like LinkedIn, email, and the phone become ways of cultivating relationships instead of starting them. #socialselling #authenticity #AI #sales #prospecting Anthony Carlson Becky Brown Todd Caponi Ari Jubelirer Jeff Rosset Ryan Rhoten Richard van der Blom Brooke Huckabee Lenny Goldman